road trips boston

Peggy's cove lighthouse sunset ocean view landscape in Halifax, Nova Scotia

Best Road Trips From Boston

Top road trip destinations from boston.

Niagara Falls

🚗 470 miles ⏱️ 7 hours

No matter what time of the year you visit Niagara Falls, you will fall in love with its majestic scenery. If you travel during the warmer months, you can take a boat tour to see the raw power of nature up close.

Get ready to explore beautiful cities and landscapes in Upstate New York as you drive past Albany , Syracuse , Finger Lakes and Buffalo en route.

New York City

🚗 215 miles ⏱️ 4 hours

If one city has something unforgettable for every type of traveler, it is the Big Apple. Spend some time at Times Square, explore world-class museums, enjoy Broadway shows and visit the iconic landmarks.

This drive features a great mix or urban and natural, and you can visit places such as Wells State Park , Wadsworth Atheneum Museum of Art in Hartford and New Haven en route.

Portland, Maine

🚗 110 miles ⏱️ 1 hour, 50 minutes

Portland is a coastal gem known for its lighthouse-dotted landscapes. From strolling along the cobblestone streets of the Old Port to treating yourself to fresh seafood and craft beer, Portland is the quintessential New England town.

En route, you will find plenty of amazing new places to discover on the coast, such as Maudslay State Park , Portsmouth Market Square and the cute towns of York and Ogunquit .

Panoramic view of the stunning fall colors and blue waters of the Bay in Acadia National Park

Acadia National Park and Bar Harbor

🚗 320 miles ⏱️ 6 hours, 30 minutes

Acadia National Park is one of the most-visited parks in the country and it is easy to understand why. Hike granite peaks, bike historic carriage roads, and witness sunrise at Cadillac Mountain where the mountains meet the sea.

This drive is a feast for the eyes with endless coastal scenery in Portsmouth , York , Ogunquit and Portsmouth as well as a dip inland to visit the beautiful town of Augusta .

Washington DC

🚗 440 miles ⏱️ 7 hours, 40 minutes

A visit to Washington DC, is a must for any history buff. Here, you can tick iconic landmarks off your bucket list, such as the Lincoln Memorial, the Smithsonian Museums, and the White House.

Some of the charming New England towns you can visit en route include Hartford and New Haven as well as iconic cities such as New York and Philadelphia .

Wooden bridge across lagoon to small island with vibrant sunset

Cape Cod and Provincetown, Massachusetts

🚗 120 miles ⏱️ 2 hours, 20 minutes

Cape Cod and Provincetown are amazing summer destinations. Known for its stunning beaches, historic lighthouses, and buzzing arts scene, this picturesque peninsula is also a great place to enjoy whale watching from mid-April to October.

You can expect some inspirational oceanside scenery on this drive, and visit Plymouth , Sagamore Beach , Nickerson State Park and Cape Cod National Seashore .

Philadelphia

🚗 400 miles ⏱️ 7 hours, 10 minutes

If you have spent some time in the US, it is likely that you are familiar with the Liberty Bell and Independence Hall in Philadelphia. Come here for history, and you will end up staying for the eclectic neighborhoods and the famous Philly cheesesteak!

You will drive past a beautiful stretch of New England on this drive, and get to spend time at Providence and New Haven , followed by a quintessential visit to the Big Apple .

Skyling of Providence, Rhode Island from across the Providence River.

🚗 50 miles ⏱️ 1 hour

If you are looking for the perfect blend of historic charm and modern sophistication, Providence is the perfect destination from Boston. Make sure to enjoy a scenic walk around the WaterFire art installation.

Even though this is a relatively short drive, there is plenty to see en route, such as the Quincy Quarries Reservation , Blue Hills Reservation and the beautiful F. Gilbert Hills State Forest .

Quebec City

🚗 390 miles ⏱️ 7 hours, 40 minutes

For a slice of Europe in North America, Quebec City is a UNESCO World Heritage site famous for its fortified colonial core and stunning Château Frontenac. Here, you will enjoy the French heritage of the city and its delicious cuisine.

This cross-border adventure will take you past Portsmouth , Portland and Augusta before you cross into Canada to visit Saint Georges before you reach your destination.

Toronto, Canada skyline with purple light and the city in the background reflecting in the water in the foreground.

🚗 600 miles ⏱️ 9 hours

Discover Toronto, Canada's largest city! From its easily recognizable CN Tower to its bustling markets, expansive green spaces, and waterfront districts, you will find plenty to do in this charming city.

Before you travel across the border into Canada, you can visit the New York State Capitol in Albany and Saratoga Springs , as well as Kingston and Oshawa once in Canada.

🚗 985 miles ⏱️ 14 hours, 50 minutes

You will immediately recognize the famous Chicago skyline as you approach the Windy City, full of Midwest charm. Dive into the city's jazz and blues scene, savor deep-dish pizza, and visit iconic sites like Millennium Park.

En route you will drive through many iconic cities on this drive to Chicago, such as Albany , Syracuse and Cleveland as well as visit the Finger Lakes .

High rise buildings with sunlight hitting at an angle and red and yellow fall colours on the trees in the foreground

🚗 300 miles ⏱️ 4 hours, 45 minutes

A relatively manageable drive across the Canadian border and you will find yourself in Montreal, home to the historic streets of Old Montreal and Mount Royal Park, which features stunning views and snowshoeing and tubing in winter.

Driving north to Canada, you will get to visit Montpelier and Burlington in Vermont, which is particularly beautiful in the fall, before crossing the border.

Nova Scotia

🚗 660 miles ⏱️ 14 hours, 30 minutes

Nova Scotia is located where the Atlantic Ocean meets rugged coastlines and jaw-droppingly beautiful landscapes. Another destination where you can admire historic lighthouses and indulge in fresh seafood.

This drive will take you past one coastal view after another such as in Portland , Bar Harbor and stunning Acadia National Park before you reach Canada.

Myrtle Beach

🚗 930 miles ⏱️ 17 hours, 10 minutes

Head to Myrtle Beach for a fun-filled getaway in the heart of the Grand Strand. Enjoy miles of sandy beaches, amusement parks, and live entertainment. This family-friendly destination offers something for everyone.

There are plenty of amazing places to visit on this route, such as New York , Philadelphia and Virginia Beach . You can also see the wild horses of Chincoteague National Wildlife Refuge .

Raleigh, North Carolina, USA downtown as viewed from the Capitol Building grounds.

🚗 730 miles ⏱️ 12 hours, 20 minutes

Raleigh is the capital of North Carolina, known for its pretty parks, and historic sites. When in Raleigh, we recommend visiting the North Carolina Museum of Natural Sciences and strolling through the beautiful Pullen Park.

This drive is an urban adventurer's dream with New York , Baltimore and Washington DC directly en route. You can also make a detour to Richmond .

Longer road trips from Boston

Orlando, Florida, USA at Universal studios city walk with a view of the Lighthouse, entrance to Islands of Adventure.

🚗 1,400 miles ⏱️ 23 hours, 40 minutes

From the magic of Walt Disney World to the popular rides of Universal Studios, Orlando offers endless fun for families and visitors of all ages.

Miami, Florida, USA with a skyline view of the city, palm trees and sea in the foreground.

🚗 1,580 miles ⏱️ 25 hours

Soak up the sun in Miami, famous for its stunning beaches, and glitzy nightlife. During the daytime, you can enjoy a tour to view the Art Deco buildings of South Beach.

Los Angeles

🚗 3,115 miles ⏱️ 48 hours

Famous for its iconic Hollywood Sign, always-busy Venice Beach, and glamorous Rodeo Drive, Los Angeles is one of the best destinations on the Pacific Coast.

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16 Fun Road Trips from Boston Only A Short Drive Away

One of the best things about taking a trip to Boston is that there’s so much to do and it’s all so easy for you to get to. You can even take a day trip to New York and head back for the evening without having to worry about losing too much time!

In fact, arguably, the biggest challenge with planning a trip from Boston is narrowing down potential destinations. Plus, there’s an international airport to consider and the option of taking a cruise from Boston to see some of the world from the sea.

Here are a few of the destinations just a short drive away from Boston that you’ll want to consider, whether you’re a Boston resident or looking to book your next road trip. Pack some snacks for the family and hit the road!

This post is part of our North American Destinations Series – you can also read more great road tripping with kids ideas here

Trips from boston: a short drive away, 1. plymouth.

Plymouth, Massachusetts, shares its name with an old English seaside town, and it’s mostly known as the spot where the Mayflower docked and established a colony 400 years ago. There’s plenty of old architecture and historical monuments around Plymouth to see, and it also has a bunch of awesome museums and restaurants to visit.

Plymouth is particularly magical around Christmas, making it one of our favorite winter destinations in the US .

No, this isn’t a typo, and you’re not going crazy. Plimoth Plantation is a sort of living exhibit where you can walk around at your leisure and experience what life would have been like as one of the pilgrims who first settled there.

This is especially a great option if traveling with kids. Many of the original machines and technologies were around at the time, making it a great way to learn a little more about history and where we all came from.

Check out these incredible Airbnb properties around New England to complete your road trip!

3. Portsmouth

Okay, now we’re just playing with you. Don’t make the mistake of getting these three very different destinations confused with each other. This coastal city is also named after an English counterpart, and it’s a great spot for everything from boat trips and fresh seafood to museums and theatres.

Better still, it’s been growing and growing in recent years and now has the infrastructure to rival anything that any other city can throw at it.

4. Newport

Also named after a British place (this time in Wales), Newport is another stunning little coastal town with plenty to offer the casual visitor. In particular, we’d recommend strolling through Brick Market Place in the city’s downtown area, which is iconic for its delicious Chinese cuisine and the wide range of shops and stores that are on offer.

The Newport Mansion at Christmas is an unforgettable experience. And if you’re a car lover, you’ll want to stop by Portsmouth (also on this list) to visit the Newport Car Museum.

5. Newburyport

Seriously, what is it with these names? This coastal town has a lot in common with some of the others on this list, except that it’s a little less busy and so it’s easier for you to lose yourself in your own thoughts while wandering around the stunning scenery.

If you can get there in the summer, all the better – the street performers will be out in full force and the beaches will be just right for a bit of sunbathing. For a small town, there’s a lot to see and do in Newburyport .

6. Lincoln

Nestled at the base of the White Mountains in New Hampshire , there’s plenty to see and do in Lincoln throughout the year. In the winter, the town really comes alive, with a range of winter sports available as well as some of the most scenic ice skating rinks that we’ve ever come across. It’s a great place to take the kids if you’re looking for something magical in the run-up to Christmas.

7. Cambridge

Are you starting to see a theme here? Also named after our friends across the pond, Cambridge MA is just as intellectual as its British counterpart. As the home of Harvard, it’s also home to a bunch of different art galleries and museums that will satisfy even the most culture-obsessed travelers. And because even the smartest college students know how to party, there’s also plenty going on in the nighttime.

8. Providence

Located in Rhode Island, Providence is about an hour’s drive from Boston and makes for a great day trip if you want to see something a little bit different. It has regular festivals and celebrations throughout the year, so if you’re thinking about swinging by then it can be a good idea to spend some time looking at what’s coming up on the calendar; fall is a busy time with leaf-peeping road trippers in New England!

You’ll find plenty of fantastic places to eat, too. We recommend scoring some Italian food on Federal Hill.

9. Martha’s Vineyard & Nantucket

Martha’s Vineyard is one of only five US place names with apostrophes in the name, something which is technically against the law . In fact, it’s only been allowed to keep it because it has so much history, and that should give you a clue about why you might want to visit Martha’s Vineyard in the first place. And as you might expect from a place named after a vineyard, the food and drink scene is fantastic .

Nearby, Nantucket Island is known for its stunning beaches , picturesque lighthouses and crashing Atlantic waves.

10. Provincetown

Based on Massachusetts’ iconic Cape Cod , Provincetown is reminiscent of San Francisco in many ways because it’s a haven for artists, actors, musicians, and more, as well as a thriving LGBTQ+ community.

There are museums and art galleries almost everywhere you turn, as well as cool specialist stores and boutiques selling handmade goodies. There’s really nowhere else in Massachusetts that’s quite like it, and it’s sure to have something for everyone in the family.

11. New York City

As we mentioned earlier, New York City is just 4 hour’s drive away, and the city that never sleeps has so much going on that you could spend a month there and not run out of things to do.

Still, you can see quite a lot in a day trip or even spend the night there to give you a little more time – there’s plenty to see and do on the drive from Boston to New York City too; we’d strongly recommend extending your trip through Upstate New York .

You can read our family guide to exploring Manhattan here .

12. Castle Hill

You’d be crazy to skip a visit to this stunning 60-room mansion. You’ll feel as though you’ve stepped out of Massachusetts and into the middle of the English countryside. At only an hour’s drive away, it’s perfect for a half-day out. Pack a picnic and a blanket to enjoy lunch on the lawn.

13. Glendale Falls

Glendale Falls offers a great excursion by providing you with some of the most awe-inspiring natural beauty the state has. It’s one of the largest series of waterfalls in the country, and there are many trails to explore.

15. Concord

Concord is a relatively small town with a big history. It’s probably most well-known for being the site of a number of battlefields and as the haunting grounds of several key figures throughout history, including writers and statesmen. Walking through Concord, you know you’re retracing famous footsteps.

16. Lexington

Lexington is known for its battlefields too, including the iconic spot on Lexington Common where soldiers fired the first shot of the Revolutionary War. Many come in droves to learn more about the history of the area and the stunning country that we live in today.

Want to extend your trip even further to Acadia National Park and the Maine coast? Try this road trip itinerary taking you all the way from Boston to Bar Habour on an epic new England Family road trip.

Planning your Boston day trips

Now that you know a few of the best places to visit while driving from Boston, it’s time for you to start planning your vacation. Remember, you can always combine multiple different destinations into a single trip by renting a car and going from city to city.

Because of that, it’s a good idea for you to go ahead and create a shortlist and an itinerary of your own, planning out where you’re going to visit, how long you’re going to stay, and which route you’re going to take.

By creating an itinerary and sticking to it, you can start to reserve hotels and other amenities to take advantage of early-bird pricing. This will save you money and also help you to avoid stressing too much in the run-up to your vacation. That way, you can just focus on having a fantastic time. Happy travels!

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Road Trips from Boston – 42 Best & fun getaway ideas for your Massachusetts scenic drive

Road Trips from Boston – Best & fun getaway ideas for your Massachusetts scenic drive

Looking to spice up your Boston adventure with an escape from the city? Lucky for you, there are plenty of thrilling road trips from Boston that you and your family and friends can hop on to and enjoy!

So, if you find yourself looking for ‘Boston getaway’, ‘best road trips from Boston’, or ‘ fun road trips near me’, then buckle up!

Drive through majestic mountains, breathtaking National Parks, and picturesque skiing destinations, or hit the coast for a seaside adventure through charming towns and villages as you take on your next Boston road trip with the help of your list of road trips from Boston ideas!

With endless options for exploration, your Boston road trip can take you on a journey of a few days or more. So sit back, relax, and let us guide you to the most unforgettable road trip experiences departing from Boston!

Editor’s Note: Our staff works hard to bring you the latest information. However, all information mentioned in this article is subject to change. As always, please confirm before heading out.

Also check our posts on Best Parks In Boston , Things To Do In Boston This Weekend , Outdoor Activities Boston , and Free Museum Days In Boston !

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Board one of the orange-and-green trolleys at any of the stops and enjoy the view with live commentary from an expert guide who knows the city inside and out. Learn about the history and happenings of Boston, a city known as the Cradle of Liberty, as the trolley rolls along from one location to the next. For one, or two consecutive days, hop off at any of the attractions for a closer look, then hop back on when it’s convenient.

14 stops and 33 points of interest!

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Road Trips from Boston – Scenic drives 2023

Mohawk trail, ma.

If you’re looking for scenic drives from Boston, the Mohawk Trail is the way to go. This 69-mile scenic route passes through deep forests and historic towns. You’ll be passing world-class art museums, early 20th-century tourist destinations, scenic hikes, and dramatic vistas. All the while, you’ll also be crisscrossing and paralleling five major rivers—the Millers, Connecticut, Green, Deerfield, and Hoosic. It’s quite the scene alright.

Driving time: 2 hours

Martha’s Vineyard, MA

Road Trips from Boston | Image credit: Visit Martha’s Vineyard

Getting to Martha’s Vineyard might not take the whole day, however, for you and your companions to fully enjoy your road trip there, an overnight stay might be better. There, you can take a scenic drive through any of the island’s six beautiful towns. Enjoy the sights of dramatic cliff-lined shores or shop in their quaint Main Street.

Driving time: 2 – 3 hours

Provincetown, MA

For a Boston scenic drive, head on over to Provincetown. This quirky town at the tip of Cape Cod boasts art galleries, beaches, and a vibrant LGBTQ+ culture. It’s also the kind of town where you can indulge in a bottomless brunch right before you head out to see the Pilgrim Monument on the spot where the Mayflower Pilgrims first set foot in the New World.

Driving time: 2 hours and 14 minutes

Lake Winnipesaukee, NH

Lake Winnipesaukee is the biggest lake in New Hampshire. And it’s a picture-perfect summer destination for locals and tourists alike. It’s a great Boston getaway destination if you and the family are into boating, fishing, and water sports.

Driving time: 2 hours

Kancamagus Highway, NH

Road Trips from Boston | Image credit: White Mountains New Hampshire

One of the best scenic drives from Boston you can take is through the Kancamagus Highway. It’s known as one of the best Fall Foliage viewing areas in the country. In addition to that, it takes you through the White Mountains which is a great place for hiking trails, mountain views, and spectacular waterfalls.

Driving time: 2 hours and 8 minutes

Franconia North State Park, NH

Enjoy the beautiful outdoors at the Franconia North State Park for your Boston road trip. This scenic park is perfect if you’re looking to enjoy a bit of everything to do with the outdoors including hiking, biking, fishing, and swimming.

Acadia National Park, ME

Road Trips from Boston | Image credit: Acadia National Park

If you’re looking for a little more thrill and adrenaline rush for your outdoor activities, check out the Acadia National Park for your Boston to Maine road trip. This park has a huge focus on adrenaline-pumping activities like biking, hiking, rock climbing, and horseback riding.

Driving time: 4 hours and 33 minutes

Road Trips from Boston – Places to go within 3 hours

Image credit: Destination Salem, Massachusetts

Just by its name, you might have had a hint that this coastal town is the premiere destination for all things spooky. Visiting it in October for its vibrant Halloween season is definitely a great to-do for your Boston road trips. But it’s also a great place to visit all year round with plenty of museums and trial sites to check out.

Driving time: 30 – 40 minutes

Plymouth, MA

If you’re looking for a quick and easy Massachusetts road trip, Plymouth would be a fun way to go. It’s known as America’s Hometown and is filled with a rich history. With that, you’ll see plenty of historical markers and historic buildings. Aside from that, there is also plenty of outdoor activities, parks, and beaches worth seeing.

Driving time: 40 – 50 minutes

Gloucester, MA

Gloucester might be the most authentic and picturesque fishing centers you’ll ever have the privilege of seeing. “America’s Oldest Seaport” also doubles as a center for painting and printmaking and an haven for the arts. A little outside the main stretch, check out Dogtown Commons for some of the most unique walking trails in the country.

Driving time: 42 minutes

Rockport, MA

Road Trips from Boston | Image credit: Rockport USA

Rockport is a picturesque seaside town with art galleries, beaches, and seafood restaurants. Despite being a small town, it has plenty of character and would really invite you to slow down from the bustling Boston lifestyle. A day or two here would truly relax and refresh you.

Driving time: 50 – 60 minutes

Cape Ann, MA

Cape Ann might not be as glamorous as Cape Cod but it’s still a place worth visiting. You can check out quaint little villages straight out of a movie set and fill up on delicious lobster served in so many ways. It’s also a great place to relax away from the fast life of the city.

Driving time: 52 minutes

Take a trip to Lowell and explore the historic mills which once powered this country’s textile industry. Check out The Boott Cotton Mills Museum, National Streetcar Museum, and The New England Quilt Museum. And get lost in the booming arts scene at the local favorite Mill No. 5 converted mill.

Driving time: 34 minutes

Providence, RI

Image credit: GoProvidence

Providence is home to famed schools Brown University and the Rhode Island School of Design. But if you’re not there for the education, that’s okay too because Providence is actually a fun place to be a tourist in. With tons of restaurants, shops, nightlife, and history to check out, this city makes for an amazing road trip from Boston.

Driving time: 1 hour

Portsmouth Harbor Lighthouse

Road Trips from Boston | Image credit: Friends of Portsmouth Harbor Lighthouses

Portsmouth Harbor Lighthouse is a great place to go if you’re looking for great ocean views. The historic lighthouse offers tours and spectacular views of the Atlantic Ocean. You’ll also get a bird’s eye view of Fort Constitution, which is situated adjacent to the lighthouse, as well as the opportunity to admire the lighthouse’s working fourth-order Fresnel lens up close.

Driving time: 1 hour and 9 minutes

Ogunquit, ME

One of the best Boston to Maine road trips you can take is to Ogunquit, a beach town that will surely delight beach lovers. It has both sandy beaches perfect for swimming and dramatic and rocky coastlines great for sightseeing. And once you get there, you can get almost everywhere on foot making it a perfect short but sweet getaway.

Driving time: 1 hour and 15 minutes

Nubble Lighthouse, ME

Cape Neddick Lighthouse, also known as Nubble Lighthouse, is one of Maine’s most popular attractions. And it’s definitely worth visiting on your road trip from Boston. Here, you’ll get to see the beautiful local scenery, get amazing views from the park, and explore the lighthouse’s rich history.

New Port, RI

Road Trips from Boston | Image credit: Discover Newport

New Port is also called the Sailing Capital of the World and the Queen of Summer Resorts. So there you have it in a nutshell. The best part is that it’s technically a city so you can have fun at the beach and enjoy all it has to offer while still getting the convenience a city has to offer.

Driving time: 1 hour 30 minutes

Road Trips from Boston | Image credit: Mystic Aquarium

This adorable little town has a great mix of nature, small-town charm, and maritime history. Go on sunset or moonlit cruises or grab a warm delicious lobster roll. You can also check out the Mystic Aquarium where you’ll see beluga whales, penguins, sharks, and sea lions. This is a great Boston getaway if you simply want to chill.

Portland, ME

Road Trips from Boston | Image credit: Visit Portland Maine

Portland is a vibrant coastal city that provides the best of both worlds for being a city and coastal destination. Enjoy everything here from a dramatic coastline to their amazing food scene on your road trip from Boston with friends or family.

Driving time: 1 hour 45 minutes

Cape Cod, MA

Cape Cod is the ultimate beach getaway Boston road trip. With over 15 towns for you to choose from to visit and over 500 miles of shoreline to explore, you’ll feel like you’re in a whole other world. Fill your time checking out beautiful little coastal towns, eating fresh seafood, enjoying the cool waters, and gazing at beautiful sunsets.

Ipswich, MA

Ipswich is the perfect place for nature lovers out there. It boasts beautiful vast open spaces and beautiful waters where you can go canoeing or boating. The town also has fantastic trails and state parks where you can bike, hike, and walk.

Driving time: 46 minutes

Newport Vineyards, RI

Road Trips from Boston | Image credit: Newport Vineyards

If you are fond of wines and great food, the Newport Vineyards is a destination you must pass by on your road trip from Boston. This winery provides tastings and tours. They also have a farm-to-table restaurant where you can enjoy the very best of the produce of the area. It’s a perfect getaway for couples or friends looking to spend intimate time together.

Driving time: 1 hour and 16 minutes

Burlington, MA

From incredible shopping and famous local restaurants to history, art, and exciting sports, you’ll find local New England culture surrounding you in Burlington. Here, you’ll be able to find a bit of rest and a slower pace from the big city.

Marblehead, MA

Marblehead would just be a quick Boston scenic drive. Situated along the North Shore of Massachusetts, this place is filled with small-town charm, dramatic, rocky coastlines, options for beaches, great seafood, and historical homes. It’s the perfect place to lay back with the family.

Portsmouth, NH

If you’re looking for a place with character to go to for your Boston road trips, you should definitely check out Portsmouth. It’s a city but it feels more like a cozy little town. Here, you’ll find plenty to check out with their quaint shops and boutiques. It’s also known as a huge foodie destination.

Brattleboro, VT

Boston already has a thriving arts scene but another place where you can enjoy a blooming arts community is the town of Brattleboro in Vermont. This town has a great arts and culture scene and a big part of that is the Brattleboro Museum & Arts Center. Aside from checking out their museums, you can also grab some fresh produce at their farmer’s markets and go on a shopping spree at their shopping alleys.

Woodstock, VT

Woodstock has that perfect New England charm and while it’s a favorite place for tourists because of that, it also doesn’t lose its local character. It’s also the kind of idyllic town that writers write about. Here, you can lay back, relax, and simply enjoy small-town life. Walk through the quaint neighborhoods, check out the orchards and farms, or simply check out the local cafes and shops.

Driving time: 2.5 hours

North Conway, NH

North Conway is a great Boston getaway to step back from the busy life of the big city. You can shop tax-free at the North Conway Settlers Green Outlet Village, see a play at one of the area playhouses, take a scenic ride and a dip in the cool mountain waters, or grab a souvenir from one of the local hand-craft, antique and gift shops.

Driving time: 2 hours and 33 minutes

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Road Trips from Boston - 42 Best & fun getaway ideas for your Massachusetts scenic drive

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Simply save the pass (available as your ‘ticket’ after purchase) on your mobile device and go. No voucher redemption is required. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for the remaining number of days purchased.

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Road Trips from Boston – Destinations between 3 to 10 hours

Manchester, vt.

Road Trips from Boston | Image credit: Visit Manchester

If you’re looking to disconnect and relax for a moment, head on over to Manchester, Vermont for your road trip from Boston. From everywhere here, you’ll be able to see tall mountain peaks. And there are various outdoor activities waiting for you. These include hiking the Lye Brook Falls trails, hiking or driving up Mt. Equinox, the tallest mountain in the Taconic Range, or going for a dip in the Dorset Marble Quarry.

Driving time: 3 hours and 10 minutes

Niagara Falls, NY

Road Trips from Boston | Image credit: Niagara Falls Tourism

If you’re going to New York for your Boston road trip, then you might as well pass through these world-famous waterfalls. Go on a boat tour and feel the splash of the waterfalls or stay on the observation deck to take in the views. You can also check out Niagara-on-the-Lake, a quaint Canadian town known for its wineries, theaters, and historic sites.

Driving time: 7 hours

Green Mountains, VT

For those up for a little more adventure, take your Boston road trip to the Green Mountains of Vermont. In the winter, there are three ski resorts you can visit to enjoy plenty of skiing and other wintertime activities. In the summer, you can enjoy hiking along some of the most famous trails in the country. Both the Appalachian Trail and the Long Trail pass through the area and share the route over a stretch of 100 miles

Driving time: 3 hours and 47 minutes

Bennington, VT

Bennington is a historic town and a great place to pass by on your Boston road trip. Check out historic sites, museums, and art galleries, and take a quick tour of the past while appreciating your history. You can also visit the Bennington Battle Monument and take a few snaps along the way.

Driving time: 3 hours and 7 minutes

Montreal Botanical Garden, QC

The Montreal Botanical Garden is for the avid plant lover. The garden has a rich collection of 22,000 plant species and cultivars. And they’re distributed throughout 10 exhibition greenhouses and some 30 thematic gardens which make the destination all the more spectacular. It’s a great place to stop by for families who’re looking to stretch their legs and enjoy wonderful sights.

Hudson Valley, NY

Hudson Valley has a reputation for being incredibly charming. And it’s an amazing place to relax and simply see where the day goes. For suggestions, you can go antiquing, take a boat cruise, explore the local galleries, check out the wineries, tour the historic mansions, and do plenty of other outdoor activities.

Driving time: 3 hours and 18 minutes

Road Trips from Boston | Image credit: Go Stowe

Head on over to this picturesque mountain town for your road trip from Boston for tons of outdoor fun. In the winter, it’s a well-known ski destination. And in the warmer months, you can switch out skiing for hiking and sightseeing for some of the town’s fantastic covered bridges.

Driving time: 3 hours and 20 minutes

New York City, NY

Image credit: Times Square, New York City

New York City is known for many things and much like Boston, it’s a place to be for many young people right now. However, it’s most known for its artistic prowess and the talents it holds. Unlike any other place in the world, stepping into the entertainment scene here would feel completely different. Aside from that, you can enjoy the history of the city, its museums, the food scene, and the stunning galleries.

Driving time: 4 hours and 16 minutes

Philadelphia, PA

If you’re interested in taking a city break while appreciating American history right where a lot of it happened, taking your road trip from Boston to Philly is the way. The City of Brotherly Love is deeply rooted in history and has plenty of places where you can soak it all up. Aside from that, there are all kinds of things to check out from exciting nightlife and amazing food to parks and waterfront activities.

Driving time: 5 hours

Montreal, QC

Being the second largest city in Canada, Montreal boasts plenty of attractions for everyone to enjoy. For one, you should check out the historic architecture. Then, you should check out the festivals. Here, there is a festival for almost every main music genre out there. And, of course, don’t forget to explore the food scene. The cuisine in Montreal is extremely diverse and dishes here will be like nothing you’ve ever tasted before.

Driving time: 5 hours

Montauk, NY

Image credit: Visit Montauk

For scenic drives from Boston, heading to Montauk is a great one. On the way, you’ll be able to pass beautiful sights. And when you get to the coastal town, you’ll be greeted with beaches, lighthouses, and a cozy summer vibe. You can also find hiking trails, music and art festivals, seafood restaurants and more to enjoy. For the kids, there are plenty of fishing, surfing, and padding activities to enjoy.

Driving time: 5 hours and 12 minutes

Toronto, ON

From one city to another. Get a feel of what city life is like in another corner of the world in Toronto. This city has something for everyone. For those that love nature and outdoor activities, you’ve got Toronto Islands and the parks. For those that love sports, you have Scotiabank Arena, Rogers Center, and more. There are also beaches and plenty of museums for families. Make sure to give the city time though so you’ll be able to make the most of your time there.

Driving time: 8 hours and 40 minutes

Quebec City, QC

Image credit: Québec cité

The historic heart of Quebec City is a UNESCO World Heritage site and here, you can soak up its storied past and European charm. More than that, the fun never stops in Quebec. With a steady string of events all year round including historical festivals, theatrical happenings, and sports events, there are always tons of things to do and see. It’s also a foodie destination known for its wide range of styles with French, British, North American, and Indigenous influences. The road trip from Boston may be long but it’s one worth taking.

Driving time: 6 hours and 13 minutes

Do you have any other fun road trips from Boston ideas? Share them with us in the comments!

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Update: Some offers mentioned below are no longer available. View the current offers here .

While a typical summer weekend in Boston usually means a stroll along the Charles River or a picnic in the Common, we all know this summer won't be anything close to normal.

Travelers who need a change of scenery can find charming New England towns and untouched stretches of wilderness just a few hours from the city.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter .

From Boston , travelers can reach many exciting and overlooked destinations, such as the vertical granite cliffs of Camden Hills State Park and historic towns filled with lovely Victorian homes. If you're planning on spending more time in the great outdoors than ever before, there are plenty of opportunities for adventure-fueled days spent rock-climbing, hiking and kayaking.

Related: 6 of the best-value points hotels in Boston

Whether you're planning a road trip from Boston this summer or a year from now, remember that small New England towns are filled with intimate B&Bs and historic inns, be sure to book with a credit card that will help you maximize your travel purchases, such as the Chase Sapphire Reserve® (3x) or Chase Sapphire Preferred® Card (5x when booked through Chase Ultimate Rewars,2x on all other).

Related: Going on road trips this summer? Consider using these credit cards

And be sure to keep a great card for earning points on gas purchases in your wallet, too — especially if you're driving three hours or more outside Boston. With the Citi Premier® Card, you'll earn 3x points per dollar when you fill up at gas stations, along with 3x points on air travel, hotels, restaurants, and supermarkets and 1 point per dollar on everything else — ideal for a long weekend exploring New England, staying in charming inns and eating as much clam chowder as you can stomach.

If you're planning a near-term road trip, just remember that many states may still require out-of-state travelers to self-quarantine for two weeks. Maine's executive order , for example, requires a 14-day self-quarantine for visitors through much of the summer. Plus, many inns, restaurants and attractions may remain closed, at least to out-of-towners. So, you might want to bookmark these itineraries for later.

Related: 10 tips for anyone taking a road trip right now

Camden, Maine

Distance from Boston: 3 hours and 20 minutes

Often overshadowed by nearby Bar Harbor , Camden is a haven for outdoorsy travelers. Sure, visitors can spend an afternoon wandering up and down Main Street, stopping to admire the views of Camden Harbor or peruse the boutique shops (be prepared to spend too much on unexpected finds at Josephine on Elm Street). But to make the drive — just over three hours — worthwhile, travelers should take advantage of the destination's ample outdoor activities.

What to do : Explore Camden Hills State Park on the 30-mile trail network. One of our favorites is the moderate trail up to Ocean Lookout for an uninterrupted view of the town and harbor. If you're interested in something more, well, vertical, have Equinox Guiding Service bring you out for an afternoon of rock climbing. For a more relaxed option, head out to Savage Oakes Vineyard and Winery to sample their house blends, made with 10 grape varieties grown on-site.

Where to stay : Camden has a mix of lodging options, mostly small bed and breakfasts and inns. But 16 Bay View is Camden's newest luxury hotel, housed in a 100-year-old industrial brick building that once operated as a car dealership. For a more intimate stay, book a room at the Camden Harbour Inn , with rooms and suites that boast (as its name implies) exceptional views of the water.

What to eat and drink: Located in the Camden Harbour Inn, travelers should reserve a table on the porch of Natalie's Restaurant . If oysters are what you're after, head over to 18 Central Oyster Bar and Grill , in nearby Rockport, for a platter of their local or "away" raw oysters.

Related: Why you should visit Acadia National Park in Maine

Freeport, Maine

Distance from Boston : 2 hours

While Freeport is best known as the birthplace of LL Bean, there are plenty of other reasons to spend a weekend in town. Located just north of Portland on the shores of Casco Bay, brick buildings line Freeport's streets, and shoppers wander unhurried between the outlet stores and seafood-centric restaurants.

What to do : Start your trip to Freeport by stocking up on activewear and outdoor gear at LL Bean's flagship location, which is typically open 24 hours every day. Shoppers should also check the outlets at the Freeport Village Station. Just be sure to keep a great card for everyday spending , such as The Blue Business® Plus Credit Card from American Express or the Chase Freedom Unlimited, in the front of your wallet. Afterward, head over to DeLorme, in nearby Yarmouth, to see the world's largest rotating globe (it's nearly 42 feet across), or take a walk through the hemlock and white pine forests of Wolfe's Neck Woods State Park .

Where to stay : The Brewster House Bed and Breakfast is an upscale inn just three blocks from the center of Freeport. Seven rooms and suites make this a great choice for a romantic getaway, or for families exploring coastal Maine. Another option is the Harbour Towne Inn on the Waterfront — a Victorian-style bed and breakfast with panoramic views of Boothbay Harbor.

What to eat and drink : Start the morning with a cup of the daily roast from Coffee By Design , a sustainable cafe located inside the LL Bean store. Linda Beans is a favorite for seafood (order the classic Maine lobster roll) right on the main strip. Outdoor seating with fire pits makes this a great spot during cool, early summer evenings. Visitors should also sample Maine Distilling 's Blueshine blueberry liquor when the distillery is open for tastings.

Related: The 7 best 'secret' swimming holes to visit this summer

Stockbridge, Massachusetts

Surrounded by the mountainous terrain of the Berkshires , Stockbridge is a small town in rural Massachusetts with the culture and arts scene of a big city — with none of the traffic or crowds. Summers are usually filled with music festivals and theater, and travelers can also explore the area's extensive hiking and biking trails.

What to do: Founded in 1934, the Berkshire Botanical Garden (closed until further notice) is a 15-acre public garden that showcases local flora alongside contemporary sculpture exhibitions. Need a more strenuous activity? The Laurel Hill Association maintains three hiking trails in the Stockbridge area — the Mary Flynn Trail, Laura's Tower Trail and Ice Glen Trail. After a day of hiking or strolling through the gardens, travelers can typically catch an opera or theatrical performance at the historic Mahaiwe Performing Arts Center (closed until further notice). And, if you have the time to dedicate during your weekend trip, head to the Kripalu Center for Yoga and Health (closed for the remainder of 2020), a retreat offering a mix of yoga, writing and Ayurveda courses, among others. Programs typically last for at least two days.

Where to stay: The Stockbridge Country Inn is located within walking distance of multiple area museums. Its location on four acres of manicured lawns and gardens, complete with a patio and heated outdoor pool, make it a great place to relax and enjoy a hot summer afternoon. The Inn at Stockbridge is another option, with 15 rooms spread throughout a renovated barn, a Victorian-style mansion in which many original antiques remain and a cottage house. When Miraval finally welcomes visitors to its third resort in the Berkshires , guests can focus on wellness and mindfulness. After all, it wouldn't be a Miraval resort without a full spa experience. Miraval resorts occupy their own lane in the World of Hyatt award chart, and a free night will cost you 45,000 points, plus an additional 20,000 per night for an additional guest in your room.

What to eat and drink: Providing food and accommodations to visitors for over two centuries, The Red Lion Inn serves traditional New England cuisine (along with an expansive wine list featuring over 400 different selections). For classic European dishes (think: escargot pot pie), try Once Upon a Table , which also dishes up more hearty, regional fare (crab cakes, for example).

Related: 4 incredible fall foliage drives in the Northeast

Woodstock, Vermont

Distance from Boston : 2.5 hours

Located in the heart of the Green Mountains, Woodstock is the quintessential New England town. New openings and upgrades over the past few years have transformed this drive-by town into a popular (and rather upscale) getaway for New Englanders. A pedestrian-friendly downtown is filled with small shops, inns and restaurants, while the surrounding rural landscape invites visitors to explore and unwind.

What to do : As the Northeast's premier skiing destination during the winter months, many of Vermont's ski resorts are overlooked as soon as the snow melts. For this reason, the local ski hill, Suicide Six, has a new mountain bike park, which has miles of machine-built trails that are free to use. If extreme sports are not for you, take a tour of the Billings Farm & Museum when it reopens (you'll get a firsthand look at what farm-to-table actually means). Woodstock and the surrounding hills are also great for cross-country cycling. Travelers will discover rural roads that meander along streams and past historic farmhouses. Before driving back to Boston, drop by the farmer's market to stock up on fresh snacks.

Related: Attractions worthy of a family road trip in Vermont

Where to stay: The Woodstock Inn and Resort has 142 traditional rooms and suites that mix history (like handmade furniture) with modern amenities (think: Wi-Fi, Nespresso machines and flat-screen televisions). Located about nine miles from Woodstock in Barnard, Twin Farms is an exclusive five-star resort spread across 300 acres. The all-inclusive has a renowned culinary program — and a price tag to match.

What to eat and drink: With thousands of farms in the state of Vermont, food in the Green Mountain state is incredibly fresh. Worthy Kitchen , for example, has a rotating menu based on what's in season, as well as a beer list that showcases some of the state's finest craft breweries, including Hill Farmstead and the Alchemist. At Soulfully Good Cafe , visitors can try the signature cream apricot scones for a sweet breakfast on-the-go.

Related: Use your points and book a staycation at one of these 7 kid-friendly resorts

Narragansett, Rhode Island

Distance from Boston: 1.5 hours

This coastal Rhode Island town is a classic New England beach destination, with four of the state's arguably most popular beaches nearby. Visitors will get their fill of local seafood while exploring the oceanfront, or venturing to nearby Block Island or Newport .

What to do : Situated on 60 acres of state parkland, The Scarborough State Beach boasts more than 2,000 feet of sandy ocean frontage and is home to a newly renovated pavilion. Narragansett Beach may be one of the best on the East Coast, and if lighthouses and history are your thing, visit the historic Port Judith Lighthouse, which was first constructed in 1806. The Towers, or Twin Towers, is another landmark structure, and it's the only remnant of the Narragansett Pier Casino, which was the heart of Narragansett during the late 19th century. Today, the restored Towers typically host an assortment of events, including dance lessons and musical performances.

Related: 5 ways to explore Newport this summer

Where to stay : Many of the rooms at the Aqua Blue Hotel have full or partial ocean views (and balconies), and it's centrally located in town. There are also several bed and breakfasts, such as the Ocean Rose Inn , which overlooks Newport Harbor, Narragansett Bay and Jamestown Island. Eighteen new rooms were revealed in 2017 as part of a property renovation.

What to eat and drink : Built in the late 1800s by the U.S. Coast Guard, this granite structure is now home to the Coast Guard House , a seafood restaurant perched on Narragansett Bay. If you overslept, head to Crazy Burger (hear us out). In addition to an eclectic vegetarian-friendly menu with items like the Poco Loco Vegan Burger, the restaurant usually serves breakfast until 4 p.m. daily.

Additional reporting by Melanie Lieberman.

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Travel and Blossom

A travel and lifestyle blog for female solo travelers who want to learn how to travel with confidence

30 Best Road Trips From Boston

Fall Travel , North America , Spring Travel , Summer Travel , Winter Travel / April 2, 2022 by Jade / 16 Comments

Planning a road trip from Boston and don’t know where to go? Check out this post on the 30 best road trips from Boston.

As someone who doesn’t know how to drive yet, I’ve been dying to do a road trip out of Boston for quite some time now. However, until I’m able to get my license, my dream road trip out of Boston will have to wait. So, instead of pouting about as I wait for my license, I’d rather take this time to tell you some of the best road trips you can take out of Boston.

Table of Contents

New England Bucket List Series

P.s. this is a post in my new england bucket list series. here is the complete series:.

Road Trips: 30 Best Road Trips From Boston

Ice Skating: The Top 7 Places for Free Ice Skating in Boston

Hiking: 20 Best Hikes for Fall Foliage in New England

Fall Foliage: 12 Best Places for Fall Foliage in Boston

Thrift Stores: The 7 Best Thrift Stores in Boston for Vintage

Salem: One Day in Salem Massachusetts: Hocus Pocus Edition

Museums: The Top 8 Free Museums in Boston for College Students

Newport, RI (best road trips from Boston)

A trip to Newport, RI is one of the best road trips you can take out of Boston! The road trip will take about 90 minutes by car and there are a lot of fun things to do ! In fact, according to Pamela, Aquidneck Island is also home to Newport! In the island, you will find a lot of breathtaking sea cliffs around the Cliff Walk. The Cliff Walk is a 3.5 mile walk around the shore that shows off the breathtaking views of the mansions and the area. The Breakers is one of the most famous mansions around the area and it has tours available all year round .

Newport is also most popular during the summer due its wide range of water-based activities. Boats line the water all around Newport, and sailing is a common pastime in the area. However, if you’re visiting during the spring or fall, the nature’s colors will also inspire you!

The Naval War College Museum is also worth checking out if you’re looking to learn more about Newport’s history. Bowen’s Wharf and its neighbor Bannister’s Wharf , are even home to a variety of locally-owned shops and restaurants!

Overall, the elegant blend of history, nature and food is what makes Newport a great road trip to take from Boston.

By: Pamela of Directionally Challenged Traveler

Portland, ME (best road trips from Boston)

A trip to Portland, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 45 minutes to complete and you can do a lot of fun things while you’re there .

In fact, according to Kelly, while the fastest way to get to Portland from Boston is via I-95, this highway can often become inundated with traffic once in a while. Therefore, if you have the time, taking Route 1 along the coast is your best option. Not only will it show you some sweeping views of the Atlantic, but you can also make some stops at some iconic places along the way like Ogunquit , Old Orchard Beach , Kennebunkport , and Cape Elizabeth .

In addition, feel free to make a pit stop at the Holy Donut on your road trip if you need food. You can order a sea salt and chocolate potato doughnut once you’re there as well as some coffee.

By: Kelly of Girl with the Passport

Newburyport, MA (best road trips from Boston)

A trip to Newburyport is another great road trip you can do from Boston! The road trip will take about 45 minutes to complete and you can stop by Salem on the way there too.

In fact, according to Newburyport.com , there’s no shortage of things to do in this city. For example, the Clipper City Rail Trail is a 1.1 mile path that runs from the MBTA all the way to the Merrimack River Shoreline. You can run, walk, or bike on this path as you pass by some popular spots like the Graf Ice Skating Rink or the Cashman Park .

In addition, the Waterfront Park is another popular spot you can go to in Newburyport. It has ample green space that is used for sunbathing, relaxing, and hosting events.

Portsmouth, NH (best road trips from Boston)

Portsmouth, NH is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Market Square once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Portsmouth. For example, Prescott Park is a popular attraction that is located along the banks of the Piscataqua River. It has beautiful gardens of perennial flowers as well as a performance space and public docks.

In addition, the Prescott Park Arts Festival is also held at the park. This festival brings in many theater performances each summer as well as music.

Provincetown, MA (best road trips from Boston)

A trip to Provincetown is another great road trip you can take out of Boston! The road trip will take about two hours and a half to complete and you can do a lot of fun things while you’re there.

In fact, according to Vicky, you can take a sand dune tour at Provincetown’s Cape Cod National Seashore Park as well as climb to the top of the Pilgrim Monument for some amazing views.

In addition, there are many different art galleries you can visit in town. The gallery district is located in Provincetown’s East End section and it has Friday night art openings every week .

By: Vicky of Buddy The Traveling Monkey

Westerly, RI (best road trips from Boston)

A trip to Westerly, RI is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can check out Taylor Swift’s house once you’re there.

In fact, according to Business Insider , Taylor Swift bought the Rhode Island mansion for 17.75 million in 2013. She even paid for the entire mansion in CASH ! Imagine that. Taylor Swift is not only wealthy but she’s also not afraid to make a grand gesture.

Since then, the musician is continuing to put her home to good use by hosting A-list parties and events.

Lake Champlain, VT (best road trips from Boston)

A trip to Lake Champlain is another great road trip you can take out of Boston. The road trip will take about five hours to complete and you can visit the Waterfront Park once you’re there.

In fact, according to Inspirock, Lake Champlain also offers a range of different activities for outdoorsy fans as well as an exciting food scene. For example, the Burlington Bike Path is a great path near Lake Champlain where people can ride their bikes along the lake.

Lake Champlain also has a shop called Lake Champlain Chocolates where people can buy chocolate bars, truffles and caramels.

Plymouth, MA (best road trips from Boston)

A trip to Plymouth, MA is another great road trip you can take from Boston! The road trip will take about 40 minutes to complete and you can visit Plymouth Rock once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Plymouth. For example, the National Monument to the Forefathers is a popular tourist attraction that is located along Allerton St in Plymouth. The monument commemorates the founders of the Plymouth colony and it was dedicated in 1889.

In addition, try to see if you can do a Native Plymouth Tour once you’re there. This tour will help you see all that Plymouth has to offer with a Native American perspective.

Rockport, MA (best road trips from Boston)

Rockport, MA is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can snap pictures at Motif #1 once you’re there.

In fact, according to Addison Choate, Rockport has plenty of things to do that are under the radar. For example, just off the coast of Rockport you can visit Thatcher Island , an island known for its shipwrecks and for serving as a home for the mafia hitman turned informant, Joe Barboza .

He was a hitman for the Patriarca crime family during the 1960s and was a resident of the island back in 1967.

York, ME (best road trips from Boston)

A trip to York, ME is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can visit some other beautiful towns in Maine once you’re there.

In fact, according to Amanda, York has that classic coastal New England charm with its clapboard houses and stark white lighthouse. That stark white lighthouse in particular is called the Nubble Lighthouse .

Built in 1879, it is known to be haunted in York, ME by the ghost ship Isadore that wrecked nearby. If you’re interested in entering the lighthouse on your trip, go at your own risk. The lighthouse is not currently open to the public so it will be difficult.

By Amanda of Hey! East Coast USA

Block Island, RI (best road trips from Boston)

A trip to Block Island is another great road trip you can take out of Boston. The road trip will take about three hours to complete and you can go bike riding, kayaking and parasailing once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do on the island as well. For example, you can check out the views at the Mohegan Bluffs .

The Mohegan Bluffs are large clay cliffs that are located on the south shore of the island. They have views that are undoubtedly the best on the island, as you take in the scenery from the water and the beach.

Acadia National Park, ME (best road trips from Boston)

A trip to Acadia National Park is another great road trip you can take out of Boston! The road trip will take about five hours to complete and you can visit the Park Loop Road once you’re there.

In fact, according to James Ian, when you get to Bar Harbor, the gateway town to Acadia National Park, you can easily spend another few days there or even a week.

The area is known for its prime lobster fishing hub in Maine where you can order fresh seafood right from the water’s edge.

In addition, Acadia National Park is a hiker’s paradise. It has dozens of trails available through the woods that offer incredible views of the surrounding oceans and islands. These trails include but are not limited to the Beehive and the Precipice .

By: James Ian of Parks Collecting

Charleston, RI (best road trips from Boston)

Charleston, RI is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the East Beach while you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Charleston as well. For example, Charleston has a top rated tourist attraction called the Fantastic Umbrella Factory .

It is known as a 19th century farmyard shoppers paradise in Charleston where visitors can shop at stores and admire local artwork. These stores include but are not limited to the General Store and the Frills. Local artwork can also be admired in the factory at the Henna Body Art.

Gilford, NH (best road trips from Boston)

Gilford, NH is another great road trip you can take from Boston! The road trip will take about an hour and a half to complete and you can visit the Gunstock Mountain Resort once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Gilford as well. For example, Gilford has a top rated tourist attraction called the Pepi Herrmann Crystal Gallery and Museum that features a wide range of crystal objects’d art like jewelry, Christmas ornaments, barware, home decor pieces, and stemware.

So, if this is of interest to you, feel free to stop by this attraction on your trip. Once you’re there you can also purchase and take home a small, inexpensive gift.

The Berkshires, MA in general (best road trips from Boston)

In the winter, a trip to the Berkshires is another great road trip you can take out of Boston! The trip should take about two hours to complete and you can go cross country skiing and snowshoeing once you’re there.

In fact, according to Karen, numerous hikes are also available through the Berkshire Hills. These hikes include but are not limited to Race Brook Falls, October Mountain Loop and the Bash Bish Falls.

The Bash Bish Falls in particular is where you can go to admire the highest waterfall in the state.

By: Karen of Outdoor Adventure Sampler

Gloucester, MA (best road trips from Boston)

A trip to Gloucester, MA is another great road trip you can take out of Boston. The road trip will take about 50 minutes to complete and you can visit the Good Harbor Beach once you’re there.

In fact, according to Addison Choate, Gloucester has plenty of things to do that are completely under the radar. For example, in Gloucester, you can visit the Hammond Castle Museum that’s located in the Magnolia area on the Atlantic coast.

The castle, which was constructed between 1926 and 1929, was also the home and laboratory of John Hays Hammond, Jr ., who was an inventor and pioneer in the study of remote control.

Lexington, MA (best road trips from Boston)

A trip to Lexington, MA is another great road trip you can take out of Boston. The road trip will take about 30 mins to complete and you can visit the Wilson Farm once you’re there.

In fact, according to Trip Savvy , there are a lot of other things you can do in Lexington as well. For example, in Lexington, you can visit the Lexington Battle Green where the American Revolution began. This spot also showcases the Revolutionary Monument which dates all the way back to 1799.

In addition, the Lexington Venue is also a great place to catch a movie. It’s a small town movie theater with two screens that shows a variety of feature and independent films.

Plum Island, MA (best road trips from Boston)

A trip to Plum Island is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit Bob Lobster once you’re there.

In fact, according to New England, there are a lot of other things you can do in Plum Island as well. For example, on the island, you can visit Plum Island Beach which is 42 miles away from Downtown Boston.

Therefore, if you’re planning on checking out this spot for the first time, I highly recommend going before sunset. This will give you the chance to see the beach as the sun sets so that you can take great pictures.

Kennebunkport, ME (best road trips from Boston)

A trip to Kennebunkport, Maine is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the Seashore Trolley Museum once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Kennebunkport as well. For example, Kennebunkport has a top rated tourist attraction called the First Families Kennebunkport Museum.

It is operated by The Kennebunkport Historical Society and you can find it in an 1853 Greek Revival home on Main Street in a village.

Lenox, MA (best road trips from Boston)

A trip to Lenox, MA is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit The Mount, Edith Wharton’s Home once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do in Lenox as well. For example, Lenox has a top rated tourist attraction called the Berkshire Scenic Railway Museum .

It is an all-volunteer, non-profit organization dedicated to preserving the history of railroading and trolley lines in the Berkshire Hills of Western Massachusetts.

Ipswich, MA (best road trips from Boston)

A trip to Ipswich, MA, is another great road trip you can take out of Boston. The road trip will take about 40 minutes to complete and you can visit the Castle Hill on the Crane Estate once you’re there.

In fact, according to Travel Lens, there are a lot of other things you can do in Ipswich as well. For example, in Ipswich, you can meet some wolves at a top rated tourist attraction called the Wolf Hollow .

It is a non-profit wolf sanctuary and educational hub that’s dedicated to preserving the wolves in the wild with education and exposure.

Ogunquit, ME (best road trips from Boston)

A trip to Ogunquit, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 20 minutes to complete and you can visit Ogunquit Beach once you’re there.

In fact, according to Visit Maine, there are a lot of other things you can do in Ogunquit as well. For example, in Ogunquit, you can visit a top rated tourist attraction called Perkins Cove.

It is a small turn of the century fishing village that draws in great crowds every summer due to the boutique shops and fresh seafood.

Kittery, ME (best road trips from Boston)

A trip to Kittery, ME is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Kittery Historical and Naval Museum once you’re there.

In fact, according to The Crazy Tourist , there are a lot of other things you can do in Kittery as well. For example, in Kittery, you can visit a top rated tourist attraction called Badger’s Island.

Badger’s Island is an island that sits right in the middle of the Piscataqua River where several important boats were built many years ago. These boats include but are not limited to the Ranger, America, and Raleigh.

Westford, MA (best road trips from Boston)

A trip to Westford, MA is another great road trip you can take out of Boston. The road trip will take about 45 minutes to complete and you can visit The Butterfly Place once you’re there.

In fact, according to Boston Central , there are a lot of other things you can do in Westford as well. For example, in Westford, you can visit a top rated tourist attraction called Kimball Farm Mini Golf .

This attraction has two 18 hole adventure style miniature golf courses as well as a 6000 square foot bumper boat pond.

Fall River, MA (best road trips from Boston)

Fall River, MA is another great road trip you can do out of Boston! The road trip will take about an hour to complete and you can visit Battleship Cove once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, just down Water Street, you’ll find the City Gates Plaza, which is a tribute to the city’s sister city of Ponta Delgata.

In addition, this city also has the home of the famous axe murderer, Lizzie Borden . However, since the home is vacant, it is now being used as a Bed & Breakfast for tourists. So, if you like dark tourism and psychopathy, this spot is for you!

By: Kathryn of Staying Afloat Blog

Middlefield, MA (best road trips from Boston)

A trip to Middlefield, MA , is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit the Glendale Falls once you’re there.

In fact, according to Tripadvisor , there are a lot of other things you can do in Middlefield as well. For example, in Middlefield, you can check out Andrew’s gallery, DeVries Fine Art International Inc. , at the River Studio in the city.

The studio also has different series of Andrew’s sculptures that include but are not limited to dance, figurative, and abstract.

Sutton, MA (best road trips from Boston)

A trip to Sutton, MA is another great road trip you can do from Boston! The road trip will take about an hour to complete and you can hike the Purgatory Chasm once you’re there.

In fact, according to Sutton Mass, there are a lot of other things you can do in Sutton as well. For example, in Sutton, you can visit a top rated tourist attraction called Waters Farm .

In Waters Farm , you can enjoy horse drawn carriages in the summer, sleigh rides in the winter, and a wealth of other fun activities in between.

In fact, in my opinion, summer is the best time to visit since you’ll have the opportunity to participate in one of their festivals.

New Bedford, MA (best road trips from Boston)

A trip to New Bedford is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can follow the Self-Guided New Bedford Art Walk once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, in New Bedford, you can explore a beautiful collection of murals scattered across the city.

In addition, you can also immerse yourself in New Bedford’s beautiful architecture by walking along the city’s cobblestone streets.

Cape Cod, MA in general (best road trips from Boston)

A trip to Cape Cod is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can stop by the Cape Cod National Seashore once you’re there.

In fact, according to the U.S. News and World Report , there are a lot of other things you can do in Cape Cod as well. For example, in Cape Cod, you can visit a top rated tourist attraction called Cape Cod Rail Trail.

Previously known as the Old Colony Railroad corridor, the Cape Cod Rail Trail is considered to be one of the best biking trails in New England.

Agawam, MA (best road trips from Boston)

A trip to Agawam, MA is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can visit Six Flags New England once you’re there.

In fact, according to Theme Parks and Entertainment , Six Flags New England is known for having some of the best roller coasters in the world. These roller coasters include but are not limited to The Great Chase, Catwoman’s Whip, and Goliath.

Superman The Ride is also the best ranked roller coaster in the park while The Great Chase is the worst.

Overall, I really hope you enjoyed this post on the 30 best road trips you can take from Boston! Please let me know in the comments down below which road trip destination you would like to visit the most! I would love to hear from you. 🙂 P.S. If you’re looking for some things to do in NYC, check out this post on the 101 things you can do alone while you’re there.

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The Best Road Trips from Boston

Last Updated on July 28, 2024 by Kristin

Boston is a living American history lesson, boasting Revolutionary War landmarks like the Old North Church and Freedom Trail. With an endless array of incredible seafood restaurants and charming Irish pubs, it’s worth spending time in Boston to enjoy all the city has to offer. At the same time, New England’s biggest city is also a launch pad for a road trip to the numerous small towns dotting the Atlantic coast. Here are the best road trips from Boston.

Fabulous Road Trips from Boston

Note: Drive times are estimates, and can vary greatly due to New England traffic.

25 miles / 32 mins.

The quick jaunt northeast up I-93 and I-95 to Salem, Massachusetts may not seem like a proper road trip. However, this quaint city known for its witchcraft trials is a must-see attraction that quickly transports visitors to another world. Settled in 1626, the coastal city provides a mix of historical attractions like the Salem Witch Museum and a 171-foot replica of the Friendship merchant ship. Salem’s charming downtown is also home to an eclectic mix of specialty shops and cozy restaurants. >> Recommended hotels in Salem

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Newport, Rhode Island

84 miles / 1 hr. 30 mins.

Head south from Boston on I-95 to reach Rhode Island, a tiny state packed with sprawling mansions, world-class museums and sandy beaches. The quaint coastal town of Newport is a popular summer haven known for its stately historic homes and breathtaking coastline. Stop by the Vanderbilt family’s summer home (called The Breakers) and drive down Ocean Avenue to enjoy one of the best spots in New England for sunsets. >> Recommended hotels in Newport

Portland, Maine

112 miles / 1 hr. 45 mins.

Just a couple hours north up I-95 from Boston lies Portland, Maine, a charming port city known for craft breweries and lighthouses dotting Casco Bay. To catch an incredible sunset, drive about 15 minutes south to the Portland Head Light lighthouse in Fort Williams Park. One of the best things about a road trip to Portland is stopping at great beach towns along the way, including Ogunquit, Kennebunkport and Old Orchard Beach. >> Recommended hotels in Portland

116 miles / 2 hr. 10 mins.

A trip to Cape Cod region from Boston is a must, especially in the summer months. To make the most of this road trip, cruise through the Cape’s historic towns, including Sandwich, Orleans and Wellfleet. The last stop on this route is the iconic Provincetown, known for its inclusive culture and LGBTQ+-friendly nightlife. Try to avoid driving from Boston to Cape Cod on Friday evenings in the summer, as this route becomes logjammed with heavy traffic as people leave the city for the weekend. >> Recommended hotels on Cape Cod

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White Mountain National Forest, New Hampshire

130 miles / 2 hr. 20 mins.

For an outdoorsy road trip that takes you off the beaten path, set your sights on New Hampshire’s White Mountain National Forest via I-93. The forest spanning more than 750,000 acres is home to lakes, streams, hiking trails, ski areas and wildlife including moose, foxes and black bears. Accommodations range from campgrounds to luxury resorts with amenities like hot tubs and pools. One of the best scenic drives through the White Mountains is a 34.5-mile part of NH-112 known as the Kancamagus Highway (or “The Kanc”), which people flock to in the fall to watch the leaves change colors.

The Poconos, Pennsylvania

308 miles / 4 hr. 59 mins.

Pennsylvania’s Pocono Mountains offer an easy-access mountain getaway in whatever flavor you want. Whether you are coming in the winter for snowy fun at the Big Boulder Ski Area or visiting in the summer for hiking, biking and water sports, you’ll find plenty of places to stay, from camp-style lodges to big resorts to casino hotels. >> Recommended hotels in the Poconos

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30 Best Road Trips from Boston: Destinations To Explore

Boston is an incredible place, one that I lived in for several years. But every so often, I needed to get out of the city and make a day trip somewhere nearby. Boston is central to a number of places, and here are my suggestions for the best road trips from Boston. I sort them by distance so you can choose the trips that best fit your schedule.

Ready to head to Boston? Here are some handy resources!

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Where Can I Drive To From Boston?

If you have a vehicle, I would absolutely recommend leaving Boston, but if you’re going to stay in the city, read my article about Driving In Boston or Best Food in Boston . Within 6 hours of Boston, you can hit the Quebec Province of Canada , Maine , New Hampshire , Vermont , Connecticut, Rhode Island, New York, New Jersey, and Pennsylvania.

Is driving in Boston hard? Find out here !

What cities are within driving distance from Boston?

We defined driving distance as within 6 hours. That gives you time to make the drive there, explore and make it back in less than a day. So, here is our list of 30 best road trips within driving distance of Boston.

Where can you drive in 6 hours from Boston?

Lancaster, pennsylvania (6 hours: 2 minutes).

In a world in which malls are becoming less common, Park City Center Mall is the largest mall in South Central Pennsylvania, with over 150 stores. Also in town is the Lancaster Central Market, the oldest continuously operated farmers market in the US. Which sells Amish goods not commonly found anywhere else. Finally, for watch enthusiasts, the National Watch & Clock Museum has the largest collection of closes and watches in North America.

Quebec City, Quebec (5 Hours: 58 Minutes)

Located on the north bank of the St Lawrence River, this Canadian city has lots of European designs to it. Areas such as Vieux-Quebec, Chateau Frontenac, and Notre-Dame de Quebec Cathedral have beautiful architecture. Just note that the primary language is French, you’ll still find some English speakers in the more touristy areas.

Atlantic City, New Jersey (5 Hours: 26 Minutes)

Known for its casinos, boardwalks and beaches, this is a popular tourist destination. Additionally the 9 casinos in one city is one of the ways it resembles a smaller version of Las Vegas. They also have 3 large shopping centers, 2 convention centers, and numerous beaches. Lastly, for fans of Monopoly, all of the spaces are named after locations in and around Atlantic City.

Philadelphia, Pennsylvania (5 Hours: 2 Minutes)

The largest city in Pennsylvania, and one of the leading cities in higher education in our country with 18 universities and colleges. Philadelphia was also our first US Capital which means there is lots of history in it. Additionally, the most famous monument being the Liberty Bell. is found here. The city has the most outdoor sculptures and murals of any US city.

Road trip from Boston to Bar Harbor to see beautiful lighthouses and landscapes.

Syracuse, New York (4 Hours: 31 Minutes)

Incorporated in 1825, Syracuse has grown substantially as a major hub and education center of New York with Syracuse University and two SUNY universities. With a huge arts focus, it is home of the Syracuse Jazz Festival and Polish Festival. It also has orchestras, opera companies, several theatres, and 5 museums.

Bar Harbor, Maine (4 Hours: 27 Minutes)

Located on Mount Desert Island and is home to Acadia National Park. Acadia National Park is a beautiful coastal park with hiking trails, boating, and camping. Home of Jackson Laboratory and MDI Biological Laboratories with a focus on marine life research. With over 2 dozen hotels and nearly 200 cruises arriving every year, it’s evident that this is a tourists favorite destination.

Long Island, New York (4 Hours: 12 Minutes)

The longest and largest island in the contiguous United States, Long Island is the most populated island anywhere in the US. With 8 big sports stadiums, golf courses, horse racing, and the national tennis center. It is truly a great place for sports lovers. In addition to theatres, music venues, and other entertainment venues, it’s definitely got the big city feel.

Road Trip Destinations around 3 hours from Boston

New york city, new york (3 hours: 12 minutes).

What’s better than a road trip to the Big Apple? With 5 boroughs, hundreds of diverse neighborhoods, skyscrapers, and Broadway, you could spend weeks in New York without getting bored. It is the city that never sleeps for a reason. Just note, that traffic in and near New York City can be a nightmare.

Pro Tip : if the traffic and parking in NYC is stressful, consider taking a train! It takes about as long as driving but you don’t have to worry about a car.

Danbury, Connecticut (3 Hours)

Nicknamed the “Hat City” due to its ties to the hat industry. Danbury is ranked as the most diverse city in New England by WalletHub. With lots of parks, hiking trails, and a railroad museum, there are some fun things to see and do. If you like old buildings, they have 12 on the National Registry of Historic Places.

Schenectady, New York (2 Hour: 59 Minutes)

Settled in 1661, this small (10.98 square mile) city still has lots to offer. With a golf course ranked as “Best places to play” by Golf Digest. This small city also boasts some beautiful architecture, as well as the first planned residential neighborhood and college campus. The Rivers Casino and Resort is worth visiting as well.

Bridgeport, Connecticut (2 Hours: 54 Minutes)

The largest city in Connecticut, and a major shipping port, this city got its start in 1821. Infamous showman P.T. Barnum was a resident and housed his circus in Bridgeport in the winters. Home of the world’s first Subway restaurant and where the electric plug outlet was invented. Additionally with 1,300 acres of green space in 35 community parks, the city has earned the nickname “Park City.”

North Conway, New Hampshire (2 Hours: 52 Minutes)

A small little town in New Hampshire, North Conway was originally chartered in 1765, nestled in the White Mountains. A perfect place for those who love outdoor activities. The Echo Lake State Park provides boating, swimming, and rock climbing. In the winter, Cranmore Mountian Resort provides 200 acres and 54 trails of skiing.

Trumbull, Connecticut (2 Hours: 52 Minutes)

With 20 local parks and one big state park, Trumbull has lots of green space to enjoy. In addition to the parks, they have four sites on the National Registry of Historical Places. If you happen to be around in October 2097, they buried a time capsule to be opened then.

Martha’s Vineyard, Massachusetts (2 Hours: 50 Minutes)

About a third of the travel to Martha’s Vineyard includes the ferry ride. However you can take your car over, so it’ll still count as a road trip with beautiful on-ocean views. Technically there are 6 towns on the island, but in a lot of ways they work together as one. With a long list of famous individuals having homes or regularly visiting the island, including 3 former presidents, it has been nicknamed “Hollywood East.”

Road Trip from Boston to Martha's Vineyard to see the beach and this iconic lighthouse

Killington, Vermont (2 Hours: 47 Minutes)

Chartered in 1761, and then renamed in 1999, Killington is home to the Killington Ski Report. The largest ski area in the Eastern US. Nicknamed the “Beast of the East,” the resort has 155 trails, 21 lifts, and just over 1,500 acres to ski. With the town having less than 2,000 permanent residents, skiing is the only reason to trek out to Killington.

Killington, Vermont is also a great place to visit in the fall for all the incredible fall foliage . Enjoy driving around Vermont to see everything the state has to offer.

Albany, New York (2 Hours: 43 Minutes)

The capital of the state of New York since 1797 when the US was formed. It is also the longest continuously charted city in the United States, starting in 1686. As a major city, it has all of the attractions of a city, without all of the people. 70% of their permanent population comes from the 7 colleges and universities within Albany, including the nationally recognized SUNY Albany.

Road Trip Destinations within 2 hours from Boston?

Newport, rhode island (2 hours: 4 minutes).

Known as the Sailing Capital of the world, Newport has several big claims to fame in the sports arena. The first U.S. National Tennis Championships, the second is the home of the National Sailing Hall of Fame and finally, the International Tennis Hall of Fame. They also have a close relationship with the navy, housing the Naval War College and Naval Undersea Warfare Center since 1861.

Berkshire, Massachusetts (2 Hours: 2 Minutes)

In Massachusetts, when you want to get away to somewhere quiet and relaxing, it’s often a day trip to the Berkshires. With lots of history, good food, shopping, and lots of outside activities, it’s a great escape from the city. Additionally it has so many cute hotels and AirBnBs for a relaxing getaway.

Enjoy some more great small towns in Massachusetts here !

Kennebunkport, Maine (1 Hour: 45 Minutes)

Originally settled in 1653 as part of Massachusetts, Kennebunkport is another beautiful coastal town. Along with the numerous beachfront hotels, it is also the summer home of former presidents George H. W. Bush and George W. Bush. With lots of summer activities and miles of beaches, it’s a popular tourist destination.

Portland, Maine (1 Hour: 41 Minutes)

The largest city in Maine, with ocean views and vibrant nightlife. Old Port hosts dozens of restaurants and bars all within walking distance of each other, it’s known as a destination for foodies. Additionally there’s two big universities, a baseball stadium, a basketball court, an observatory, and a large few large performance venues. They have something for everybody.

Providence, Rhode Island (1 Hour: 41 Minutes)

The capital and largest city in Rhode Island was settled in 1636. It was also one of the original thirteen colonies. Now it’s a growing city with eight hospitals, eight institutions of higher learning, several museums, the oldest baptist church in America, and a zoo. Of course, you can’t forget the roadside attraction, Nibbles Woodaway , the world’s largest artificial bug atop the Big Blue Solutions building.

Ogunquit, Maine (1 Hour: 31 Minutes)

Another oceanside town settled in 1641, it served as the first sawmill in the United States and grew into a shipbuilding town. Famous for fishing, it currently has a Museum of American Art, a playhouse, and a couple of beaches. With a population of less than 2,000 year-round residents, it’s one of the least populated towns on our list.

Road Trip Destinations about an hour from Boston?

Cape cod, massachusetts (1 hour: 15 minutes).

A peninsula extending into the Atlantic Ocean, it includes 15 unique towns. It’s broken into Upper Cape, Lower Cape, and Mid-Cape. If you like seafood or lighthouses (there are 19 of them), this is a beautiful drive with friendly locals.

Wachusetts, Massachusetts (1 Hour: 5 Minutes)

Another great ski destination, and one of the ones listed in our Best Skiing in New England article . With 100% snowmaking capacity and night skiing on most trails, it’s a great local mountain. In addition to the ski resort, there is a Great Wolf Lodge located nearby with indoor pools and water parks.

Want more great ideas for ski resorts in New England? See our article about the Best Skiing in New England .

Hampton, New Hampshire (1 Hour: 3 Minutes)

Heading north from Boston, you’ll the little town of Hampton, NH. While over 2,000 of the homes in town are for “seasonal or recreational use,” meaning that they have lots of rental housing if you wanted to spend the night. They are most popular with summer tourists, with a beach, a state park, and a music venue.

Rockport, Massachusetts (55 Minutes)

One of our favorite places to visit and walk around downtown. Founded in 1840, it’s right on the coast and has beautiful views of the ocean. With a very walkable downtown (and even colored routes marked out on the sidewalk), and lots of cute local stores, you could spend hours and not run out of things to see.

A cute little ice cream store in Rockport, MA - One of the best road trips from Boston

Worcester, Massachusetts (51 Minutes)

The second most populated city in New England, Worcester also has the second largest art museum in New England and the oldest pipe band in the US. It’s also home to Worcester Polytechnic Institute, Worcester State University, and College of the Holy Cross, one of the oldest Catholic colleges in America, and 6 other universities. Additionally it has all the activities of a big city without the crowded streets.

Plymouth, Massachusetts (50 Minutes)

Home of Plymouth Rock , where the pilgrims landed in 1620, making it one of the oldest colonies in the United States. Also the home of America’s first thanksgiving feast, this is a town that embraces its history at the start of our country.

Road trips from Boston to Plymouth, MA to see a lobster statue

Salem, Massachusetts (40 Minutes)

First settled in 1626 by English Colonists, Salem was a major seaport for the North Shore area. Most famously known for the Salem Witch Trials, they take Halloween and all things witches very seriously. They seem to celebrate Halloween all year long , with year-round haunted house tours, psychic conventions, and lots of ghost stories.

Foxborough, Massachusetts (39 Minutes)

Once home to the world’s largest straw hat factory, it’s now known most commonly as the location of the Gillette Stadium. Gillette Stadium is home to the New England Patriots Football team, but is also a FIFA World Cup location in 2026. Outside of the stadium is primarily support businesses, such as the restaurants and shops in The Patriot Place Shopping Plaza.

Enjoy some fun Boston-specific events like Boston First Night or Boston Marathon .

How Far Is It From Boston To The Maine Border?

From downtown Boston to the Maine border is just about an hour, making it a very easy day trip. Maine has some beautiful ocean views and island escapes. If you wanted to continue your drive through Maine, see our Maine Category for some great ideas. If you’re trying to decide between visiting Maine or New Hampshire though, there are definitely pros and cons to both.

How Far Is It From Boston To The New York Border?

From downtown Boston to the New York border is about 3.5 hours, or 183 miles, making it a very easy day trip. New York, Long Island, and New Jersey are all great locations for all of the activities of the big cities.

5 one-tank road trips from Boston, Massachusetts

Use this guide for inspiration for your next locally-based road trip from Boston—without needing to stop for gas

By Roadtrippers

Between high gas prices, limited vacation days, and chaotic air travel, taking a local road trip is more appealing than ever this summer. These five destinations are all within 300 miles (round-trip) of Boston, Massachusetts, making them ideal for quick getaways. Spend less time at the pump and more time enjoying the road.

1. Kennebunkport, Maine

Total mileage: 180 miles

Head 1.5 hours north of the city to the quintessential coastal town of Kennebunkport, Maine. Here you can kayak in the marsh, lounge on the beach, eat all of the lobster rolls you can stomach, and check out shops and cafes around Dock Square. Thanks to its location north of Boston, you’ll avoid heavy summer traffic to Cape Cod. The town is known for being the home of the Bush family compound , which you can see from the water.

Don’t miss: Hang out on Goose Rocks Beach , eat a lobster roll at Nunans’s Lobster Hut or Mabel’s Lobster Claw , take a lobster fishing boat tour, tour the First Families Kennebunkport Museum , and explore the Rachel Carson National Wildlife Refuge .

Stay: Glamp or camp at Sandy Pines Campground , located about a 15-minute drive from town. Or stay at the historic The Colony Hotel .

Charge: Some accommodations in town offer EV charging stations, and there are a few public options near town as well.

Related Jessica Fletcher’s Maine: 4 quaint seaside towns that inspired the fictional village of Cabot Cove

2. Provincetown, Massachusetts

Total mileage: 230 miles

Located at the tip of Cape Cod, Provincetown (or P-Town) is a vibrant, LGBTQ-friendly beach town that’s fun to visit any time of the year. Expect heavy traffic when driving from the city during peak times in the summer, or you can opt to take a ferry. But once you’ve arrived, you’ll feel like you’re a world away from Boston. Come for a themed-event weekend or the annual Carnival Week, which is in August.

Don’t miss: Watch the sunset at Race Point Beach , eat at The Lobster Pot , wander through art galleries, see the Pilgrim Monument , and try malasadas at Provincetown Portuguese Bakery .

Stay: Surfside Hotel and Suites has its own private beach and is pet-friendly.

Charge: There are only a few EV chargers in Provincetown, so plug in along your route from Boston to the Cape. Energy company Eversource supports charging stations at landmarks like the Cape Cod Rail Trail, Nauset Beach , Skaket Beach , and the Jonathan Young Windmill .

3. Newport, Rhode Island

Total mileage: 140 miles

Known for its maritime history and Gilded Age mansions, Newport offers plenty of activities for a weekend—or longer. The seaside city is about a 1.5-hour drive from Boston (depending on traffic). From wandering Thames Street to eating fresh seafood and viewing a historic lighthouse on Goat Island , visitors of all ages and travel styles will enjoy the City by the Sea. Just over the Newport Bridge is Jamestown, home of various Moonrise Kingdom filming locations .

Don’t miss: Tour The Breakers , Marble House , or countless other mansions; enjoy the Cliff Walk ; eat stuffies (baked clams) at Easton’s Beach Snack Bar ; dine at the Clarke Cooke House ; and visit the International Tennis Hall of Fame .

Stay: Overnight at Gilded , a boutique hotel located just off of Bellevue Avenue.

Charge: A few area hotels offer charging stations. You’ll also find them in Fort Adams State Park .

4. Wolfeboro, New Hampshire

Total mileage: 220 miles

Located on Lake Winnipesaukee, about 2 hours from Boston, Wolfeboro is known as “America’s First Resort Town.” The quaint Main Street is home to favorites such as Bailey’s Bubble and the Yum Yum Shop . The best thing to do here is get out on the water with a boat rental and explore the lake’s many islands. Rattlesnake Island is a local gem—known for its shape, not snake sightings—and is a scenic spot for day hikes.

Don’t miss: Eat at Wolfetrap Grille and Raw Bar , rent paddleboards, have pizza at Nolan’s Brick Oven Bistro , and drink beer at Lone Wolfe Brewing .

Stay: There are plenty of cute inns in town, like the Pickering House Inn , or you can camp nearby at Wolfeboro Campground .

Charge: There aren’t many charging stations in Wolfeboro, so make sure you charge along your route. There are options along Interstate 95 to/from Boston.

5. Block Island, Rhode Island

Total mileage: 200 miles

Drive to Naragannset (Port Judith terminal) or Newport, Rhode Island, and take the high-speed ferry to Block Island. Many of the tourist attractions and beaches are walkable (or bikeable) from the ferry dock, but if you’d prefer to bring your car, you can do so via the traditional ferry (from the Port Judith terminal only); reservations must be made in advance by calling 866-783-7996, Extension 3. The ferry takes 30 minutes to 1 hour. Once you’re on the island, you’ll have plenty of beaches, shops, art galleries, and restaurants to see.

Don’t miss: Horseback ride at Rustic Rides Farm , go on a nature walk through the Nature Conservancy, eat beachside at Beachhead , and have breakfast at Ernie’s Breakfast Restaurant .

Stay: Overnight at the Block Island Beach House .

Charge: There are no public charging stations on Block Island. Charge up in Newport or Port Judith/Galilee if needed.

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Roadtrippers

Roadtrippers helps you find the most epic destinations and detours—from roadside attractions to natural wonders and beyond.

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7 Spectacular Weekend Road Trips from Boston, Massachusetts

Posted by Sarah Lamagna May 25, 2021 Updated May 21, 2024

Tired of the cobblestone streets and “R’s” left out of every word? Luckily for the residents of Boston, there are some epic weekend road trips within a few hours of the city.

Boston might be home to some incredible sights and truly dedicated sports fans, but sometimes a weekend away is just what the doctor ordered.

Whether you’re looking for gorgeous coastal villages, quaint mountain towns, some good ol’ fashioned Ben & Jerry’s ice cream, or views from the top of Mount Washington, we’ve got what you need.

Related Read: 10 Chill Romantic Getaways in Massachusetts

Road Trip Planning

Before you head out, make sure to plan accordingly. Unlike a lot of other places across the country, weather and traffic are fairly predictable in and around Boston. There usually aren’t “surprise” storms and traffic is, well, always there.

Expect typical weather patterns during corresponding seasons: it snows in the winter, rains in the spring and fall, and is hot/humid in the summer. You won’t need any special car enhancements (like four-wheel drive) to get to any of the places on this list. But beware of potholes – they are a’plenty in the northeast. Construction crews never seem to be able to keep up with them.

Speaking of construction; it’s constant in New England and especially in Boston. Construction crews are out in freezing temperatures and rainy days. Expect traffic to be slower and heavier in these areas. It’s also important to note that depending on your destination from Boston, you might pass through several rush hours.

There’s also a reason that Boston drivers are well-known across the country; they are aggressive. Come prepared knowing that if you stall too long when a red light turns green, you will definitely be beeped at – car horns are the state bird call of Massachusetts…just kidding.

Pro tip: do NOT dilly dally in the passing lane. This is a huge pet peeve of most New Englanders. If you aren’t passing someone, get out of that lane.

7 Amazing Weekend Trips from Boston

1. north conway, nh.

This picturesque town has everything you’ll need for outdoor adventure. North Conway is in the heart of White Mountain National Forest which prides itself in a myriad of outdoor activities including hiking, biking, skiing, and fishing (among others).

Mount Washington looms in the distance as if beckoning you to climb it. At 6,288’ above sea level, Mount Washington is the tallest mountain in the northeast. You can climb it anytime of year (although we recommend a guide service like Nemo Mountaineering in the winter) through several routes, with the Tuckerman Ravine route being the most popular. You can also drive up yourself during the late spring/summer months or take the Cog Railway .

The heights around Mount Washington aren’t for everyone, though. Instead, you can take a drive along the Kancamagus Highway (the Kanc to locals). It can get busy on the weekends, especially during peak leaf-peeping season in the autumn.

You can also simply hang around town: visit Zeb’s General Store , grab brunch at Peach’s Restaurant , drink a beer at Moat Mountain Smokehouse and Brewing , or visit the Conway Scenic Railroad .

Distance from Boston : 137 miles
Drive time: 2 hours, 30 minutes

2. Westerly, RI

Head on down to this southern Rhode Island beach town to catch some waves and rays (and maybe a glimpse of TSwift ). It’s the shortest trip on our list from Boston which means extra time to soak in the sun and get that tan you’ve been yearning for.

The best place for getting in that vitamin D is at Watch Hill . It’s great for kids and adults alike and includes a Merry-Go-Round where kids can take their chances grabbing brass rings for a shot at a free ride – psst…make sure to grab an outside horse to do this.

Aside from beaches, there’s plenty of other things to do including popping your head into a few boutiques like Anther Living and Rochelle’s . For some good food (or a great place to stay), check out Ocean House’s many culinary journeys including a taco shack, a secret garden creperie, and a raw bar – among so much more.

Distance from Boston : 92 miles
Drive time: 1 hour, 30 minutes

3. North Adams, MA

Grab a wand and your spell book to head to the place that inspired writers like J.K. Rowling, Henry David Thoreau, and Herman Melville. Located in northwestern Massachusetts, North Adams is in the heart of the Berkshire Mountains.

You can head up to the top of the state to visit Mount Greylock and the Massachusetts War Memorial Tower. On a clear day, you can see for 70 miles in either direction into five states.

Too bad you didn’t really know magic, though, and get yourself back down to town quickly. Whenever you do, head over to PUBLIC for some great eats and then to Bright Ideas Brewing for the best brewery in town.

Distance from Boston : 136 miles
Drive time: 2 hours, 45 minutes

4. Lake George, NY

If you’re in the mood for some lake-living, then Lake George is your answer. It’s full of every type of water-related activity you can think of: boating, kayaking, water skiing, canoeing, fishing, and even hopping on a cruise . But if water isn’t your thing, well, maybe go elsewhere?

Seriously, though, on top of every water sport in the world, Lake George has many land activities. For the most unique experience on land, though, consider taking a rail bike tour through the Adirondacks. Or you could check out the Natural Stone Bridge and Caves , which is home to the largest marble cave entrance in the eastern United States.

Distance from Boston : 227 miles
Drive time: 3 hours, 30 minutes

5. Mystic, CT

Move over Leonardo Dicaprio, Mystic is the true home of the hero of the Titanic. That is, Bob Ballard who discovered the famous ship wreckage. He founded the Institute for Exploration which partnered with the Mystic Aquarium – located in, you guessed it, Mystic.

But this quaint, coastal town is more than marine ecosystems. You can travel back in time and visit Mystic Seaport Village and set foot on a veteran training ship . If you need to pick up some trinkets for your family or friends, head to Franklin’s General Store in Olde Mystick Village . Grab a pizza slice from famed Mystic Pizza (yup, it’s the same one in the movie starring Julia Roberts). To wind down for the evening, get a scoop of ice cream from Mystic Drawbridge Ice Cream and watch the boats head down the Mystic River.

Distance from Boston : 100 miles
Drive time: 1 hour, 40 minutes

Related Read: The 6 Best Scenic Byways to Fully Experience Massachusetts

6. Stowe, VT

No matter the time of year you visit this northern Vermont town, Stowe is perfect for any traveler. Into skiing? Head to Stowe Mountain Resort . Rather have a spa day? Then Stoweflake is your destination. Or maybe you just want some ice cream? Then take a tour of the hippie owners’ flagship Ben & Jerry’s store in Waterbury (just south of Stowe).

A trip to Stowe isn’t a trip, though, until you visit the Trapp Family Lodge . You can stay there the entire weekend, grab a beer from the von Trapp Brewery , or experience one of the many activities there including disc golf, biking, hiking, and carriage rides.

Pro tip: don your best dirndl or lederhosen during their Oktoberfest . It’s a heck of a time!

Distance from Boston : 199 miles
Drive time: 3 hours

7. Kennebunkport, ME

Kennebunkport is THE quintessential New England coastal town. To get a real feel for its personality, head on out to Dock Square where you can peruse art and buy some fashionable clothing at the boutique shops or sit in one of the many cafes along the main drag.

Get your lobster fix at Port Lobster or Mabel’s (they’re both favorites for the locals) or try the famed Whoopie Pie found at HB Provisions . For adventurous souls, visit the Rachel Carson National Wildlife Refuge or kayak around Cape Porpoise Pier . End your day by resting your head (or simply walking around the 60 acres of lush gardens) at St. Anthony’s Monastery and Franciscan Guest House .

Distance from Denver : 84 miles

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Seen in: Massachusetts , New England , Road Trips

Posted by Sarah Lamagna

Sarah is an ecologist-turned-freelance writer specializing in the ecotourism and slow/sustainable travel industry. Her bylines include The Denver Post, 5280 magazine, VeryWellFamily, Matador Network, and was an expert on NPR’s The Takeaway for her work on the wildfires in Colorado.

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

Best new england road trip itineraries, places to visit in new england, off the beaten path new england road trip ideas, new england road trips costs, final thoughts about new england road trips.

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With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

snowy new england scene frozen trees and pond

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The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99, and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

road trip in new england map 4 day itinerary

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our Boston itinerary includes a visit to downtown Boston to see:

Fenway Park
The Freedom Trail
Acorn Street
Trinity Church
Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

Southend for an authentic Bostonian experience
Cambridge for Harvard and MIT
East Boston for good food and views
Walden Pond for transcendental fans
Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

Lighthouses
Charming settlements
Trinket shopping
Historical landmarks
Biking and hiking
Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

road trip in new england map 7 day itinerary

7 Days: New England’s Best Fall Foliage

Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
Spend the night in Kent, Cromwell or elsewhere.
Admire the foliage.
Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
Arrive at the junction between I-7 and Highway 2 near Williamstown.
Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
Stay nearby and drive along the 2 to your heart’s desire.
Drive on the Mohawk Trail if you haven’t already.
When ready, head for Green Mountain National Forest of Vermont via I-7 again.
Drive through the Green Mountains until Burlington.
Grab a beer and chill for the night.

Today is a long but rewarding day.

Depart from Burlington and head for Cambridge, VT.
Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
Make your way east towards Bath, New Hampshire.
Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
Continue onto Lincoln, admiring the scenery along the way.
Find a Lincoln Airbnb or stay in North Conway or elsewhere in the White Mountains.
Finish the Kancamagus Highway (112), which terminates at Conway.
Head north upon reaching Conway on Highway 16.
Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
Turn onto I-2 and then again onto 113 to reach Evans Notch.
Finish up and head south towards Portland for the night.
Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
Spend the night around Acadia or back in Portland.
Consider spending the night in Camden as there is excellent foliage here.
Pack up and head back to Boston.
Spend the day exploring the city.
Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

map of new england road trip 14 day itinerary

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here except instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
Explore the city and its architecture.
Be sure to drop by one of the many breweries and brewpubs.
Spend the night in or around Providence.
Wake up and head directly for Newport via Highway 114.
Spend the day exploring the opulent town.
Be sure to visit the many mansions and estates as well as Fort Adams in the south.
Depart when you’re ready.
Drop by Narragansett for some beach time if you have time.
Stop in Old Saybrook for the night or continue onto New Haven.
Depart from your lodge and make your way north.
Head to the state capital Hartford.
Wadsworth Falls
Buttermilk Falls
Settle in Hartford for some culture and good partying or…
Head to Litchfield Hills for a quieter night.
Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
Hit highway 7 and make the long drive to Burlington.
Reward your hard work today with a beer.
Spend the day exploring the Green Mountains of Vermont.
Climbing the Camel’s Hump .
Hiking around Mt Mansfield .
Check out Smuggler’s Notch .
Rafting on the Mad River .
Spend the night in Burlington again.
Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
Spend the remainder of the day in the mountains.
Flume Gorge
Mt Washington
Franconia Notch
Arethusa Falls
Lonesome Lake
If you arrived early enough, considering overnighting in a backcountry campsite.
Wake up and knock off any remaining activities.
Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
Lay your head down for the night, preferably around a campfire with a drink.
Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
Spend the day exploring Acadia National Park.
Taking a road trip around Mt Desert Island .
Climbing Cadillac Mountain .
Visiting Jordan Pond .
Relaxing on Sand Beach .
Walking around Bar Harbor .
Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

boston skyline from the bay new england road trip

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . You can stay in Boston , take a look at my picks. Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

cap cod beach and fences romantic new england coast road trip

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

yale university new haven coast new england road trip

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

an assortment of orange and red trees as seen from above on an autumn hike in connecticut new england usa

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

vermont snowy geen mountains new england road trip

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

white mountains of new hampshire new england

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

great north woods new hampshire new england road trip route

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

mit docks and boston skyline new england road trip roaming ralph

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental : $100-$300

Gallon of gas: $2.74

Private AirBnB home: $140

Hotel room: $150

Hostel: $25-$35

Campground: $10-30 (sometimes free!)

Sandwich: $6-$9

Beer at a bar: $5-$8

Coffee: $3-$4

Bottle of Whiskey from the market: $25

Dinner for two: $35-$60

maine coastline at dawn rocky and rugged

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

cows grazing in connecticut new england under fall trees

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

backpacker drinking using grayl geopress filter bottle

Drink water from ANYWHERE. The Grayl Geopress is the worlds leading filtered water bottle protecting you from all manner of waterborne nasties.

Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress rigorously from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

woman taking photo with new england foliage

Updated February 2023 by Samantha Shea

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You can now buy The Broke Backpacker a coffee . If you like and use our content to plan your trips, it’s a much appreciated way to show appreciation 🙂

the broke backpacker team at the water temple in bali

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Don’t forget the Berkshires, in Western Mass, start at MassMoCA in North Adams, then drive Rt 7 through Williamstown to Lenox, Stockbridge, Great Barrington..and since you’re so close you can go a little more west over to NY and visit the Catskills too if you’re feeling crazy ?

Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

Your Perfect New England Road Trip Itinerary: Plan a Road Trip From Boston

May 6, 2021

Two week New England Road Trip Itinerary

Start with a road trip from Boston. Mix lighthouses, whaling ports and clam chowder with the origins of modern America with this New England road trip itinerary. By the end, America may seem older but you’ll feel younger. Here’s how to make it happen.

Table of Contents

The Perfect New England Road Trip From boston

New england road trip itinerary map.

Drive Massachusetts Map of Boston Road Trips

A Two Week New England Road Trip Itinerary

This New England road trip itinerary follows our well-researched plans. We spent two weeks driving around Massachusetts, spending a few days in Boston and then looping through three key areas: Salem and Cape Ann to the north of Boston, historic Plymouth, Cape Cod, Martha’s Vineyard and Nantucket to the south and then inland to endless tree-lined roads in the Berkshires.

Separate stories of the people we met and the stories we uncovered will come elsewhere on the lab ( see the USA section here ), along with poetry, whimsy and the story of the invention of the first ever fried clams.

Whether you’re at the dreaming, planning or booking side of things, I present you with a nuts and bolts New England road trip itinerary to help you plan your perfect road trip from Boston.

From Massachusetts to Manhattan and Brooklyn

Another great idea is to extend your Massachusetts road trip into New York State. Brooklyn is one of the most densely populated urban areas in the world and intriguingly diverse: over 60 languages spoken in the area.

It’s also known for being an artistic hub, and a great alternative place to stay to cross the bridge and explore Manhattan. Here’s a lovely example of a boutique hotel in Brooklyn to add to your road trip plans.

Road Trip from Boston, Abigail King in front of the USA flag

Boston: Days 1-3

Spend a few days in Boston recovering from jet lag and enjoying this historic, thriving, curious, famous city often overshadowed by nearby Manhattan.

Recommended reading: Things to do in Boston and beyond .

Salem and Cape Ann: Days 3-5

The first stop on this New England road trip itinerary has history and white picket fences written all over it.

Salem’s most famous role was as the heart of the infamous Witch Trials of 1692, brought to 20 th century audiences (and schoolrooms) through Arthur Miller’s The Crucible and a subsequent performance by Winona Ryder.

The first part of the Salem Witch Museum explores story of the original trial. But even more interesting than that is the second section. Here, the conversation moves to the idea of a “witch hunt” and the process through which society mistrusts and demonises “outsiders.”

The Salem Witch Museum really isn’t suitable for children under 8. It’s dark with screaming, animated, figures and a human-size devil, so it’s the one thing I’d recommend families take in turns or skip.

Cape Ann is a gorgeously rural, windswept place with pebbly-sand beaches that lift the soul at dawn. What’s even better? You won’t find many tourists here, at least not from outside America.

As a result, a visit to Cape Ann is all about taking in nature and local customs and really slowing down.

As so many events are weather dependent (and you rarely need to book) I’d advise you look at a map and mix and match from the following. You should be able to fit everything in within a couple of days.

Watch Sunset at Pigeon Cove

This gorgeous spot has been entertaining guests since the 1850s when William Norwood set up a tavern carriage traders. In its time, it attracted literary greats like Ralph Waldo Emerson (“Trust thyself”) and Henry David Thoreau so you can feel englightened as you dine (toddler included.)

Book your spot at Emerson Inn here.

Spend the Day at Appleton Farms

Nine generations of Appletons have worked on Appleton farm , amid crumbling stone walls and one of the earliest American dreams. That makes it one of the oldest continuously operating farms in America.

Today, it’s part of the Trustees for Reservations Group (a kind of American National Trust.) Overall, Appleton aims to bring the wholesome, heritage parts of farming to city slickers and those who want to get involved.

It spreads over 1000 glorious acres of rolling grasslands and maple trees, like scenes from Jed Bartlet in New Hampshire in the West Wing. But it’s not just pretty for the tourists.

It’s a working farm and you can visit livestock, hike for hours or visit the historic farmhouse.

Catch the afternoon milking of the Jersey cows at 4:00, say hello to the chickens, goats and sheep at any time. And if you’re lucky, catch a cheese-making demonstration at the creamery.

Road Trip from Boston - Manchester on Sea Cape Ann Massachusetts

Visit the Singing Beach

Manchester’s Singing Beach has a poetic name for a poetic place. The sea may not actually sing (it’s more like a whistle) but its sense of peace was one of the highlights of this New England road trip itinerary.

Go for Dinner or Cocktails at the 1606 Restaurant, the Beauport Hotel

Join the much-feted East Coast Elite in the glory days of shipping by dining at 1606 Restaurant at the Beauport Hotel. The restaurant overlooks the sea, with a luxurious nautical theme of polished wood, white walls and knotted rope. Seduced by the gentle live music, it’s easy to believe that you too could run for office one day…

Visit the Birthplace of Fried Clams

At the other end of the spectrum is Woodman’s of Essex , the self-proclaimed “home of the fried clam.”

It’s a lovely story told by lovely people. In 1916, Lawrence “Chubby” Woodman, at the suggestion (near dare?) of a friend, decided to fry some clams ahead of the national July 4 th celebrations. Five generations and over 100 years later, the clam shack is still going strong, and the legacy of the fried clam has spread across New England.

Here, you grab a seat with friends and tuck in to a range of fried fare, including the state’s iconic clambake and the fresh lobster for which New England is so well known.

Road trip from Boston - Cape Ann Victoria Inn-1

Where to Stay in Cape Ann

We stayed at the Castle Manor Inn , a lovingly restored Victorian Inn just made for flowery dresses and Instagram. It’s situated inland, with soothing green gardens and that mix of grandeur and homeliness that buildings of that era exude.

While atmospheric, it’s probably not the best choice for young children as there’s no crib or soundproofing. But, if you’re travelling as a couple, it’s romantic, and if solo, a good place to chat over breakfast on the narrow terrace. And the staff couldn’t be friendlier.

Plymouth, Cape Cod and the Islands: Days 5-11

Now it’s time to visit all those places you’ve heard about in half-whispered dreams, novels, schoolrooms, history books and anything that probes into the life of J.F.K. Plymouth, Cape Cod and the islands.

Plymouth is where America began. Kinda.

It is where the pilgrims settled (they landed at Provincetown), and it remains the oldest continuously inhabited settlement in the United States founded by Europeans. Others may have got there first, but this was the only one to last.

Its history is fascinating and complex; its layout restfully small. It’s a walkable, beautiful grid of artsy coffee shops, bobbing boats and impressive, historic brick buildings.

But before you get there, allow your New England road trip itinerary to stop off at World’s End in Hingham and the cranberry bogs along the way.

World’s End

This unexpected wilderness between Boston and Plymouth offers a chance to get back in touch with nature and see views that haven’t changed for centuries.

Managed by the Trustees (the same ones who manage the Appleton farms), World’s End involves over 250 acres of tree-lined avenues, rocky shores, steep hills and wild grass.

Look one way to see Boston, its skyline painted in faint, pastel colours. Look the other to see a Nordic fishing village which turns out to be the New England coastline.While the buildings of New England may be old in US terms, this place is even older.

Linked to the retreat of the same glacier that led to Boston Harbor, the salt marshes and spoon shaped hills (or drumlins) look the same now as they did thousands and thousands of years ago.

The Trustees hold concerts here on a summer’s day, but, even if grey clouds roll in, a stride between the granite ledges, red cedars and blueberry thickets make the perfect exercise break on a road trip from Boston.

The Cranberry Bogs

Yes, when I heard about cranberry bogs I wasn’t that impressed.

Yes, when I saw a photo, I completely changed my mind.

Cranberries are big business in New England, with U.S. Farmers harvesting approximately 40,000 acres of cranberries each year. What makes this farming industry so much more interesting than the rest are the shimmer of the cranberry bogs come harvest time.

Full of bright red berries as far as the eye can see, farmers flood the bogs with enough water to cover the vines that carry the berries. They then use water reels to knock the fruit off and collect them with conveyors or pumps.

Alas, for international visitors, the season is short, running from approximately mid-September to early-November each year.

We stopped off at Mayflower Cranberries LLC (call ahead if you wish to do the same) in Plympton, Massachusetts to speak to owner Jeff LaFleur.

An amiable, passionate man, LaFleur has taken cranberry farming to the next level. His 112-acre farm has 236 acres of active cranberry bogs and he’s also a grower-owner for Ocean Spray Cranberries. As an aside, I had assumed that this was a big, faceless, awful corporation before this visit, but it’s actually a pretty decent co-op that benefits small farms and keeps them in trade. Jeff is a fan!

In Plymouth, you can indulge in as much or as little history as you like. Unless you’re particularly keen, though, one full day is probably enough. Spend the day from Boston to Plymouth stopping off at World’s End and the cranberries, and then give yourself one full day in Plymouth itself before driving on to the Cape.

The Plimouth Plantation is a little way out of town, but everything else is easily walkable, and it’s really the best way to get a taste of the place.

Plymouth Rock is New England’s most visited rock (drawing in more than 1million visitors each year).

This historical landmark signifies the place where the Mayflower pilgrims began Plymouth Colony, which is essentially the first permanent European settlement in New England.

You’ll find Plymouth Rock in the peaceful Pilgrim Memorial State Park on the shore of Plymouth Harbor.

Wampanoag Settlement Plimouth Plantation

The Plimouth Plantation

The open-air museum that is the Plimouth Plantation really turns the traditional idea of the American thanksgiving around.

Two villages co-exist:

the Wampanoag settlement with trailing smoke, simmering cauldrons, feathers, paints and spears.
the pilgrim settlement, where actors have British accents and talk about their journey from Leiden in Holland where they were granted asylum before they left ”to find the new world.”

A Tale of Two Sides

From a fraught narrative, the Plantation showcases both sides of the American story without passing judgement. Leave at least a full afternoon to really make the most of it.

Where to Eat in Plymouth

Kiskadee Coffee Company – for local art, simple snacks and, well, good coffee.
The Water Street Café – head to this diner for an all American breakfast you’ll never forget. Order crunchy French toast and consume more calories in one sitting than you even do at Christmas. Guilty. Delicious. Fun.
Dillon’s Local – we enjoyed this so much, we went back twice. ;-) Cosy, yet hipster eatery with classics like New England clam chowder and more modern arugula grilled peach salad.

Where to Stay in Plymouth

We stayed at the John Carver Inn & Spa , right within walking distance of town.

It’s a curious spot, with a mix of themes and styles, but rooms are spacious and well stocked. There’s a fantastically outrageous swimming pool with a full size replica of the Mayflower (with a bit of artistic license!).

After you check out, it’s time to grab your swimwear and prepare to head to the Cape…

Road Trip from Boston - 4Martha's Vineyard Massachusetts-1

Cape Cod and the Islands

This is the section of a Boston road trip that takes the most planning before you go.

But, oh my, is it worth it.

There is a spirit around the Cape that is simply unique. The curling tip of land that tickles history, the roar of the waves and the sharks that circle around. The taste of the air and the stick of the salt and the sense that adventure and the open world wait just around the corner.

And truthfully? We should have planned a little better and given ourselves more time. Not because there are so many things to do (there aren’t really), but because this is a place to slow down and not really think about things to do.

Recommended reading: how to plan a road trip by yourself

Fitting the Pieces Together For Cape Cod and the Islands

Station yourself in Hyannis, the hub of the Cape. While not the prettiest part, that’s a bit like saying Monet’s poppies aren’t as pretty as his waterlilies. It’s also close to the ferry port, making those connections far easier.
Don’t take your car to Nantucket.
I know I keep mentioning this, but it’s important. Parking is tricky there and getting the car onto the ferry is even trickier.
I’ll write more about these areas separately, but for now, here’s the key information to help you plan your visit.

The Cape Cod National Seashore

Managed by the National Parks Service, the Cape Cod National Seashore area cuddles along the curve of the Cape, flanked only by majestic Atlantic pine, sand and the odd shark.

Arrive early as parking is limited and expensive so it makes sense to stop for a while.

Glossy, well-heeled Chatham is a delight to walk around in between its sassy book shops, art galleries and antique shops. At the “elbow” of Cape Cod, this is the point where Nantucket Sound and the Atlantic Ocean meet.

There’s easy access to a windswept sandy beach with a lighthouse that dates back to 1878. And if you’re in luck, you can catch the annual shark art festival:

Road trip from Boston - 28 Atlantic Cape Cod Massachusetts-1

Where to Eat in Cape Cod

Twenty-Eight Atlantic at Wequassett Resort – Fine dining with full views of the sea. Look out for the ash-roasted cod loin and Chatham shellfish company oysters.

The children’s menu also comes as a sail on a wooden boat and table lights come inside hollowed sea urchins.

Twenty-eight Atlantic enjoys the highest ratings on Cape Cod from Forbes, AAA, and Zagat and it’s easy to see why.

Where to Stay in Hyannis

We stayed at the Anchor In , a convenient spot in Hyannis with spacious, light rooms, well-informed staff and a small outdoor pool with a view of the marina. A cosy “old New World” library serves breakfast and drinks through the day as well.

Road trip from Boston - Cape Cod Anchor In Hyannis

How to Get From Hyannis to Nantucket

We travelled with Hy-line cruises. The journey is short (136 minutes) but leave plenty of time to board and book your ticket in advance.

There’s a small café on board and an easy chance to walk around for toddlers.

Road trip from Boston - Nantucket Massachusetts-1

Oh, how I loved Nantucket. I Really, really loved the place.

This small island, only 30 miles across, seems to tell the story of human innovation and reinvention through a series of picturesque beaches, stylish place to stay and chic spots to eat.

Architecturally, little has changed from the 17 th century whaling hey days, all wooden slatted town houses and white columned porches.

Once it was one of the wealthiest spots in the world, thanks to its whaling industry.

Road Trip from Boston - Abigail King in Nantucket

Today it welcomes tourists and grapples first hand with balancing the past, the future, sustainable tourism and identity. Nearly 40% of Nantucket is protected for conservation and the island is now a National Historic District to boot.

All of which sounds far too serious for what is, essentially, a gentrified beach resort. But that’s what makes it so interesting.

Visit the Whaling Museum to uncover a striking, poignant, provocative and unapologetic look at the realities of the whaling industry and why it was so important to the world at that time.

Finding the Beach

Brant Point is a short and easy walk from Nantucket’s centre for an iconic lighthouse shot and scuff in the sand. Watch the ferries glide in and think back to the whaling past. Don’t try to swim, though. Currents here are far too strong.

The Children’s Beach is even closer to town with a playground and kids activities on in the summer.

For further beaches and exploration, hire a bike and cycle away!

Road trip from Boston - Smores Nantucket

Where to Stay in Nantucket

We stayed at 76 Main Hotel. This gorgeous little bolthole forms part of a small local chain, called/run by Lark Hotels.

Stylish inside and out, rooms are small but deliciously designed.

There’s even a private firepit to help you embrace another Nantucket custom: melting marshmallows, biscuits and chocolate to build your own s’mores…

Martha’s Vineyard

After Nantucket, Martha’s Vineyard seems enormous and urban. But of course, in reality she’s only 25 miles across with a population of around 17,000.

Her villages have different character, but you’ll find a key blend of summer holidays and New England in each.

You can catch the ferry from Hyannis but we drove from Hyannis and picked up the Steamship Authority ferry from Woods Hole to make the next part of the journey a little easier.

Arrive in good time to queue with your car but again, there’s a café and room to walk around when on board. And some spectacular views as you approach the island.

What to Do in Martha’s Vineyard

A trip to Martha’s Vineyard forms an essential part of any New England road trip itinerary. Here are the highlights:

Look out for Murdick’s Fudge
Visit Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery to meet the man who makes weather vanes for the stars (Steven Spielberg has a velociprator made on this very island.)
Feel the salt in your lungs and the wind in your hair on Martha’s sandy beaches.
Pay a quick visit to the pastel-pretty gingerbread cottages in Oak Bluffs.
See the wealth of the whaling captains in Edgartown, Martha’s first colonial settlement, through their Greek revival mansions.
Give Mad Martha’s ice cream a good licking. With a fun name like that, you may as well try one.

Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery

Where to Stay in Martha’s Vineyard

The Winnetu is the kind of place I’d love to stay at all week for one of those relax-and-forget-about-the-world holidays – with children.

It’s unusual in that it is designed with families in mind – and yet it still manages to be pleasing to the eye for adults!

Rooms have decent high chairs, cots and mini self-catering facilities but with a beautiful, New England design that appeals to adults.

The Dunes Restaurant introduced a new concept to me: adult dining with a children’s play area within the restaurant (if you don’t have kids, don’t fear, there is an adults-only section.)

The hotel’s outdoor pool is set in spacious grounds with a lifeguard and towel service and seemed surprisingly, blissfully empty for the most part. The great, green grounds led to the ocean at South Beach where it was too blustery for us to go in but seemed majestic in its beauty.

Road trip from Boston - Dr Seuss Museum Springfield Massachusetts-1

From Martha’s Vineyard to the Berkshires and Around: Days 11-14

Get ready to welcome manicured, college campus America, with a side stop into the edgier Springfield, home to the Dr. Seuss Museum and the man himself. In fact, the key draw to this region (for me) was the “Iconic Illustrators Trail” – an intriguing journey through different areas of New England, each with amazing images.

From Martha’s Vineyard to Springfield

We took the ferry from Martha’s Vineyard to Woods Hole as it shortens the driving time as compared to a return ticket to Hyannis. Check which makes the most sense for you.

Springfield was a surprising stop on this New England road trip itinerary. It broke the classic “New England” style and probably deserved a little more exploration.

Local boy Dr. Seuss (real name Theodor Geisel, ) grew up here amid the thriving inner-city medley of life with newly arrived immigrants from around the world. And The Amazing World of Dr. Seuss Museum shows how that background developed into a world-famous career through personal artefacts, photographs and handwritten notes.

However, the real scene-stealer is the whimsical area downstairs, where characters like the Lorax greet you in life-size form. It is aimed at and perfect for children.

Road trip from Boston - Adolfo Springfield Restaurant-1

Where to Stay in Springfield

We stayed at the Tower Square Hotel , a tall, slick city affair with a suite that had a separate kitchen that would have been a godsend if we’d still been weaning (it was still pretty good as we could have some family time after baby lab went to sleep in our room.)

There’s a pool with a sporty feel on one floor and an all-American breakfast available in the basement. Concierge parking and a 24-hour reception desk marked a return to city life after the blue-and-white laid-back feel of the islands.

Where to Eat in Springfield

Adolfo’s, just around the corner from the Tower Square Hotel , offers tasty, unpretentious Italian food with a local twist. Look out for the owner’s legacy on the walls…

Springfield to Amherst

What’s the reason to stop off in Amherst? Why, the Hungry Caterpillar Museum .

Of course, its real name is the Eric Carle Museum of Picture Book Art and it celebrates the work of illustrators across the world. The library arranges books by illustrator rather than author and there’s a huge room dedicated to getting arty and involved with crafts.

Local Flavours in Amherst

Just down the road is the Atkins Farms Country Market , a supermarket come delicatessen come restaurant that showcases the local farming produce. And it’s amazingly tasty.

Perfect for stocking up for picnics or dropping in for a bite to eat.

From Amherst to Northampton

This short journey only takes 20 minutes. Check in and enjoy the evening. There’s more exploring to do tomorrow.

Where to Stay in Northampton

We stayed at The Hotel Northampton . Looking for a taste of American history? This is it.

Eleanor Roosevelt, Jenny Lind, Herbert Hoover, Calvin Coolidge, Dwight Eisenhower, John F. Kennedy, and Richard Nixon all dined in the hotel’s restaurant, Wiggins Tavern , in Northampton.

Rooms are moderate sized and blissfully quiet, with cots on request and a breakfast to make Americans proud.

There’s also a fantastic toy shop across the street, with the loveliest staff. They found us lightweight building blocks that stick together without glue. Perfect for travelling. Just as an aside ;-)

Where to Eat in Northampton

Bistro Les Gras – It’s a gorgeous sunset walk through Northampton to reach Bistro Les Gras, where locals dine for special occasions (they came, they chatted, they told us.)

Amid low lights and American-French charm, try the wild gulf shrimp and lemon tart. If you have a wriggly toddler with you, it’s easy to pop out and visit the live music opposite.

Iconic Illustrators Road in Massachusetts

The Normal Rockwell Museum

The Norman Rockwell Museum tells not only the story of the world famous artist but also, in a way, the story of 20 th century America as well.

Photos, paintings, and the painstakingly relocated office of the man himself offer an insight into an America that laid the foundation for the one of today.

Tanglewood & Lenox

Tanglewood is a place to get your music groove on, as long as there’s something on. The 210 acres of the Tanglewood estate were given to the Boston Symphony Orchestra in 1936 by Mary Aspinwall Tappan and the result is half stately home gardens, half rock and roll concert venue.

Even if there’s not a concert going on, you can get in and look around.

Where to Eat Near Tanglewood

Lenox is another quintessential small New England town, with boutique art shops, white fences and cute places to eat.

Road trip from Boston - Historic Deerfield Massachusetts

Tanglewood to Deerfield

The last stop before returning to the hubbub of either Boston or its international airport is the leafy, quiet village of Deerfield. Here, historic mansions rise into the sky with the trees in this 18 th century village that simply froze in time.

Where to Stay in Deerfield

Book in advance to stay at the Deerfield Inn , right in the heart of the historic part of Deerfield. Guest rooms wear period florals, lamps and bedspreads and the dark wooden writing desks seem from another age.

Deerfield to Boston

And so, this rather epic Massachusetts road trip comes to an end.

But there’s one last stop en route to the airport: Louisa May Alcott’s house .

The author of the international bestseller published in 1868, lived here with her three sisters and parents on the outskirts of the small town of Concord.

It’s a heart-fluttering stop for literature but it also shines an interesting spotlight on society in New England at the time.

How to Make It Happen

Driving is easy in Massachusetts, even if you’re used to driving on the left. Signs are clear, fuel is easily found and all the signs are in English.

America is a country built on transport, and the love of the automobile runs deep. It is more or less expected that you’ll drive everywhere and, as a result, parking is plentiful and cheap (and public transport tends to be sporadic and awkward.) It’s one of the reasons why this New England Road Trip itinerary works so well!

Explore Our Road Trip Planner & Toolkit

Designed for those who love to travel but who hate spreadsheets, our Road Trip Planner & Toolkit system shows you a bulletproof formula for getting organised in half the time. Plus, it includes the one innocent mistake that even seasoned travellers make.

The key exceptions to this are in Boston (a big, old city where walking and public transport will serve you best) and the island of Nantucket (where cars are virtually forbidden.)

Access to the beaches at Cape Cod also require hefty parking fees as the place is so popular and the villages so small.

By and large, though, Massachusetts, like so much of America, is built for a fly-drive holiday.

Where and When to Pick Up Your Car

Spend a few days in Boston, soaking up the accent, the red-brown leafy streets, the education and the arty brunches.

Then pick up your car either at the airport or at one of the centres in town. Unlike most cities, Boston Logan International is quick and easy to get to, so if you plan on flying straight out at the end of the trip, then it’s cheaper and easier to drop off at the airport and go.

Car Hire With Perks: Hertz Gold

We rented a car through Hertz . The booking and collection process was simple, but what makes the service even better is that they have an American Road Trip Planner . It makes drafting itineraries so much easier.

It’s perhaps not a great way of calming wanderlust, but it does mean that you can quickly plan another trip; an ideal way to beat the travel blues in my opinion

If you register with Hertz Gold Plus Rewards BEFORE you make your reservation you receive better deals, the chance to skip the queues and to use the Gold Plus Rewards counter. It’s free to register and only takes 60 seconds, so it’s worth doing.

What You Need to Plan in Advance

If you really have your heart set on something in particular then it makes sense to book it as soon as you can.

For me, though, most of the joy of travel involves a certain level of spontaneity and exploration, to follow where I want to go and (excuse the cheese) allow the essence of the place to appear at its own pace.

That said…in Massachusetts there are some things you really need to book in advance.

Ferries and accommodation on the islands of Martha’s Vineyard and Nantucket are often in short supply, with a fixed number of nights bookings and timetables that you need to stick to.
Leave your car behind as you head for Nantucket (leave plenty of time to find a parking space in Hyannis as it’s a bit of a scrum. Enterprising householders nearby charge a hefty fee to let you use their driveway.)
Boston can also book up quickly and so the sooner you can nail down your accommodation and car hire there, the better.

Lock these down first then work backwards from there.

Booking Flights to Boston

Our partner for this trip, Norwegian, has increased services to Boston with a daily non stop service between London Gatwick and Boston Airport. The flights are operated by a fleet of brand new Boeing 787 Dreamliner aircraft with two cabins in premium and economy.

Fares start from £155 one way / £259 return in economy and £415 one way / £745 return in premium, including all taxes and charges.

To book visit www.norwegian.com/uk or call 0330 828 0854

Wifi On the Road

It would be optimistic and slightly romantic to think that mobile internet isn’t needed for a road trip. It’s near essential for navigation, for looking up nearby restaurants and opening times and great for contacting people back home.

Mobile internet can be expensive, though, not to mention a pain to set up if you have to get a SIM card at the airport.

We rented a mobile wifi device (aka a MiFi) on this trip. It’s really convenient for family trips because everyone can join a single device instead of replacing all your SIM cards. You also get to use your original phone number so you don’t have to worry about the logistics of checking two numbers or letting loved ones back home know.

Mobile Internet from Cellhire

Cellhire is a world leader in mobile communications , allowing travellers to stay connected all over the world. The USA MiFi is one of Cellhire’s most popular products. It’s well-loved for its instant data connectivity abroad, super-fast 4G speeds and its 5GB and 10GB bundles. The USA MiFi starts at as little as £50 a month.

Should I Travel to Massachusetts with Children?

Yes, a resounding, yes! People are friendly, polite, services work, healthcare is great and driving and parking is easy. This is America, after all. :)

However, while Florida and Louisiana seemed enthralled by our smallest travel companion, some (only some) areas we visited in Massachusetts seemed a little more reserved.

We were warmly welcomed at fine dining establishments, museums, on flights and in hotels but I’d just say that the difference between Massachusetts and the South was like the UK and the Med. Children are adored in the south, welcomed further north.

Adding More States To Your New England Road Trip Itinerary

This New England road trip itinerary focuses on Massachusetts, without apology. It’s aimed to maximise your time out exploring if you only have two weeks available, which is the standard setup for travellers from the UK.

More East Coast Road Trip Routes Along the New England States

However, there is so much more to New England than Massachusetts. By definition, it includes six states rather than one, and so add the names Maine, Vermont, Connecticut, New Hampshire and Rhode Island to your New England list.

Typically, autumn or fall is the time to make your way through these states, “leaf peeping” as you go. The colours are extraordinary, the maple syrup refreshingly sweet. There’s also winter sports and skiing in Vermont come winter and long hikes along the east coast for summer road trips. In my opinion, it’s better to take it slow and explore one area rather than trying to cram everything in. But to give you a few more ideas, here are some other New England road trips that explore the other states.

More New England Road Trip Itineraries

Rhode Island – the state so small, you can drive across it in an hour. However, here are some Rhode Island Road Trip Itineraries that take in lighthouses, natural wonders and small villages, as well as Block Island.
Here’s a road trip itinerary for Maine, taking in popular spots Portland, Camden and Park Loop Road just south of Bar Harbor in the Acadia National Park.
Waterfalls, skiing and wine routes feature in these Connecticut road trip itineraries through the Litchfield Hills and New Haven.
Explore the great outdoors of the Green Mountain State with these road trip itineraries for Vermont.
And last but not least, drive around New Hampshire’s Kancamagus Highway to the White Mountain National Forest.

Keen to travel further afield but unsure where to go? Check out our guide to choosing between Los Angeles and Miami .

Beyond the East Coast: Other American Road Trip Itineraries

New orleans, louisiana.

Let the good times roll with this fascinating and fun road trip from New Orleans. Explore the less well known parts of Louisiana and learn more about America.

Florida, West Coast Itinerary

Flit from the beach to sweeping cool art museums with this Florida west coast road trip itinerary. Discover sleepy villages and a world away from the resorts.

The Great River Road, Louisiana

Explore the grandeur and the horror of plantation life with this road trip itinerary along the Great River Road in Louisiana. Then cool off amid the marshmallow in one of New Orleans’ best swamp tours.

Plus, check out how to plan your San Francisco to Santa Barbara road trip here.

Road Trip Planning Tools and Essentials

We love, love, love a good road trip here on Inside the Travel Lab and have driven solo, as a couple, a family and with friends all over the world. It’s such a great way to get off the beaten track and to feel the sense of freedom and exploration if only for a short while.

That’s why we’ve put together a series of tools and resources to help you plan your New England road trip.

For starters, don’t miss the 53 Road Trip Essentials checklist that covers what you need to pack. Then, sign up for our free road trip training sessions, a series of three videos to help you avoid the mistakes that I’ve made.

Last, but by no means least, check out our Road Trip Planner & Toolkit. It’s a revolutionary way to organise and plan out your road trip, without spreadsheets, lost scraps of paper, headaches and overwhelm. You can check that out here.

Anything else I can help you with? Just let me know!

Disclosure – This trip was made up of some self-funded aspects and a mixture of paid/unpaid partnerships with Hertz, Visit Massachusetts, Norwegian, and Cellhire. As ever, all opinions remain my own. Otherwise, what is the point?!

If you book or buy through links on this page, we may earn a small commission at no extra cost to you. Cheers!

Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary (2024)

If you’re here, that means you’re probably planning an epic New England road trip along the coast, and man, I’m SO excited for you! Hi, my name is Sam, and I’ve been exploring this corner of the world for over 15 years now. I’ve taken countless road trips along the coast, and I’ve finally perfected my unforgettable Boston to Bar Harbor, Maine itinerary for those looking to explore the New England coast .

To date, this is my favorite road trip I’ve done, and I can’t wait for you to experience it for yourself. To help you plan the perfect adventure, I’m going to share all my expertise on this area with you, offer my best tips for planning your trip, and give you my ultimate itinerary that was years in the making.

While following along, I encourage you to tailor this itinerary to your own preferences depending on how much time you have for your trip, but I do make suggestions on how long it takes to make the drive, and see all the best places on the way.

Are you ready to start planning together? Let’s go!

Marshall Point Lighthouse in Port Clyde, Maine is a great stop to make on a Boston to Bar Harbor road trip.

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our Privacy Policy .

Road Tripping From Boston To Bar Harbor – The Basics

Before we jump into the itinerary, let’s get started with some questions you may have …

How Long Is The Drive From Boston To Bar Harbor?

If you don’t make any stops at all, and take the most direct route, the drive takes between 4 hours and 40 minutes to 5 hours, and spans about 280 miles. It could be longer depending on traffic getting out of Boston. If you happen to leave Boston during rush hour, definitely expect it to take a bit longer.

However, if taking a road trip, you could really make this drive as long as you wanted because there are so many amazing things to see along the way, and some fun detours to take. In just a sec, I’ll give you my suggestions on how long you need to make this trip and see as much of the coast as you can 😉

The Cadillac Mountain auto road in Acadia National Park, Maine just before sunset.

Is The Drive Scenic?

I think so, yes! But it kind of depends on your expectations.

While many parts of the actual drive are on highways that are kind of boring, there are so many great places to stop along the way that can make the drive very scenic. Especially if you take some of my suggested detours and scenic byways! But is every second of the drive stunning? Well, no. So it’s good to set expectations. It’s really more about the stops you make during the trip than the actual drive itself.

There are some portions of the actual drive that are very beautiful, though.

How Many Days Do You Need To Drive From Boston To Bar Harbor?

Since there are just tons of incredible things to see, I’m recommending one week, or 7-8 days, as I know that this is how much most people have to make this drive. If you have longer than a week, then I say it’s worth it to enjoy going at a slower pace. But you can definitely enjoy the top things to see in a week. This will also include two days in Acadia National Park! For my itinerary, I’m mapping out 8 incredible days for you, and you can adjust it to fit your schedule 😊

Best Time Of Year To Drive Boston To Bar Harbor

Generally, June-September is the best time to drive from Boston to Bar Harbor, as this is when you can expect the best weather, and longest days . July and August is considered peak season along the New England coastline, so this is also when you can anticipate the most crowds and highest hotel prices. But gosh, it’s so worth it!

However, I’ve done this road trip in all seasons – yep, in spring, summer, fall, and even winter! As a second suggestion, I love May to avoid some of the crowds and still enjoy mild weather, and also October to chase all the stunning fall foliage .

I’m going to give you some suggestions later in the post to turn this drive into a fall foliage adventure, so be sure to check that out if you’re planning your trip in the fall season 🍁😉

It’s also good to know that some places along the New England coast are seasonal, especially seafood shacks, boat tours, and ice cream places. If they’re seasonal businesses, it’s likely they won’t open until late May or June and begin to close down around Labor Day or only stay open possibly mid-October. But you’ll always be able to find places that are open year-round, too.

How Many Days Should You Spend In Acadia National Park?

Speaking of Acadia, that’s probably the reason you’re making this drive, right? This park is undoubtedly the top attraction in New England, and rightfully so. I always recommend a minimum of two days to explore, allowing 1 full day in the park, and then at least a half day to see Bar Harbor, which is such a charming town along the coast.

If you have more than a week for this trip, you could definitely add an extra day to Bar Harbor so you have two full days to explore the park.

Is There A Ferry From Boston To Bar Harbor?

No, there is no ferry that goes between Boston and Bar Harbor. The best way to make the trip is to drive.

The only ferry to Bar Harbor is the one from Nova Scotia, which is the CAT Ferry.

Is It Worth Going All The Way To Bar Harbor?

Oh yes! I often get asked this because Bar Harbor is pretty far up the Maine coast, and it’s one of the top attractions most out of the way in New England. But yes, Acadia National Park is absolutely worth the drive . Because there are so many great things to see along the way, and since Acadia offers some of the best and most iconic coastline views in the Northeast, it’s very much worth the effort. It’s always on my list of best places to visit in New England .

Overview: Best Stops To Make When Driving Boston To Bar Harbor

Portsmouth, New Hampshire is a charming destination to see on this road trip.

These are the top places I recommend stopping in that I think are very much worth your time. Some of them require a bit of a detour, but depending on your preferences, you’ll probably be happy you went out of your way!

→ Massachusetts North Shore : This includes Marblehead, Salem, Gloucester, Rockport, Ipswich, and Newburyport. I suggest you drive the Essex Scenic Coastal Byway on your way to or from Bar Harbor to see some of these towns, depending on which appeals to you the most. I have a slight preference for Salem, Marblehead, and Rockport, which are all small and easy to do in a couple of hours each. I’ll go more into this later in the post 😉

→ Portsmouth, New Hampshire : Pretty much just off I-95 and not out of the way at all, Portsmouth is a charming coastal city that feels more like a quaint town. Great historic New England scenery and shopping! I recommend this stop if you’re looking for more of a town vibe vs. coastline, as the coastal views here aren’t as impressive as the rest of the places on this list.

→ Southern Maine Coast : This includes places like York & Cape Neddick, Kennebunkport, and Ogunquit. I usually suggest stopping at Nubble Lighthouse in York, spending a couple of hours each in Kennebunkport and Ogunquit, and even staying the night in one of these two towns.

→ Portland, Maine : The state’s largest city is filled with lots of maritime charm, amazing dining, lighthouses, and history. If you like cities, this may be worth staying a night, but you can also see the highlights in a few hours if you’re not a city person.

→ Freeport, Maine : Home to the flagship L.L. Bean store! It’s not worth it for everyone to stop, but gosh, it’s a pretty cool place to see if you’re looking to pick-up some New England clothing and accessories.

→ Maine’s Midcoast : Between Freeport and Belfast, just before getting to Bar Harbor, there are lots of great towns along the coast to explore in this region, including Harpswell, Boothbay Harbor, Wiscasset, Rockland, and Camden. I have so many suggestions for hidden gems and places to visit along this portion of the drive, which I’ll go more into during the itinerary portion of the post!

The PERFECT Boston To Bar Harbor, Maine Road Trip Itinerary

Overview of this itinerary :.

Views along Ocean Path in Acadia National Park.

Since most people reading this will need to start and end their trip in Boston to catch a flight, that’s how I’m formatting the itinerary. You’ll be making most stops on the way to Bar Harbor, but also saving a few for the drive back so you have something to look forward to 😉

Day 1 : Explore Boston.

Day 2 : Get an early start and drive to either Kennebunkport or Ogunquit. Spend 1 night.

Day 3 : Drive to Portland to explore for a few hours, and then make your way to Camden with a few optional detours for lighthouses and great coastal scenery! End in Camden to spend the night.

Day 4 : Spend the morning in Camden, and then drive to Bar Harbor. Enjoy downtown Bar Harbor and grab dinner. Spend two nights here.

Day 5 : Explore Acadia National Park during the day, and more of Bar Harbor at night.

Day 6 : Drive to Boothbay Harbor to spend 1 night. Take a boat tour.

Day 7 : Drive to Portsmouth and spend a few hours enjoying the shops, and drive the Essex Scenic Byway along the Massachusetts North Shore to make your way toward Boston. Stay the night in this area.

Day 8 : Arrive back in Boston to head home.

Day 1: Explore Boston

Boston is the perfect starting point for most New England itineraries, but it’s also one of the top places to explore in the region, so you should definitely plan at least a full day in the city!

Rooted in history, packed with New England charm, and filled with exciting dining and cool things to do, you can actually cover a lot of ground in just a day in Boston, including the top highlights.

Here are some of the top things I suggest first-timers do :

→ Take a food tour to get a taste of what this region is all about. I have a detailed guide on all the best Boston food tours to help you pick the best one! But seafood and Italian cuisine are especially great here.

→ Visit the most charming neighborhoods , which are Beacon Hill and the North End . The North End is also where you’ll find the best Italian restaurants.

→ Stroll through the Public Gardens and Boston Common . The Boston Public Garden was the very first in the U.S., and it’s so beautiful and photogenic 😍 Boston Common isn’t as scenic as the Public Garden, but in the fall during foliage season, it’s on fire with color. Plus, they’re both really close to one another.

→ If you’re looking to do some shopping , head to Newbury Street and Copley Place .

→ Visit the New England Aquarium .

→ Explore parts (or all!) of the Freedom Trail , which is a walking tour that takes you to historically significant places around Boston. You can also take this awesome Freedom Trail tour .

→ Grab lunch or coffee at the beautiful and Instagram-worthy Tatte Bakery , which has locations around the city (you’ll see why I recommend it when you walk in 😉).

→ End your day with a nice dinner out. I love Neptune Oyster , but they don’t take reservations, and it can be a long wait time. If that’s not worth it for you, I also love the Union Oyster House for a traditional New England dining experience. But there are so many fantastic places in Boston to choose from.

Acorn Street in Boston is one of the cutest streets in the city.

How To Get Around Boston :

Boston is very walkable, and most of the tourist attractions, which are truly the top things to see in the city, are within walking distance to one another (less than a mile) in the downtown area. If you’re exploring for a day, you likely won’t need to use public transit, but may want to get an Uber or Lyft, which are widely available, just to save time (or if you’re tired!).

Where To Stay In Boston : All of these suggestions are in great locations, and within walking distance to most everything! → Boston Harbor Hotel → Revere Hotel Boston Common → The Godfrey

Day 2: Drive To Southern Maine

Watching the sunrise from Marginal Way in Ogunquit is an amazing experience. If you've been wondering, is Ogunquit, Maine worth visiting, these views definitely say yes.

First thing’s first, you’ll want to pick-up your rental car in Boston early in the morning. Then, head out to start your drive to southern Maine! During this part of the trip, you’ll pass through Portsmouth, New Hampshire, but don’t worry, we’re going to stop there on the way back 😉 To get to southern Maine, you’ll hop on I-95.

So, Ogunquit or Kennebunkport ? Well, you can do both if you want! Ogunquit is about 25 minutes south of Kennebunkport, and the biggest difference, as mentioned, is that Ogunquit is more of a beach town, whereas Kennebunkport is more of a coastal town. That said, Kennebunkport also has beaches, and Ogunquit is also just as charming – I honestly love both.

Since you’ll pass by Ogunquit on your way to Kennebunkport, you can stop by for a few hours and see the beach, and the cute little town, and then end in Kennebunkport. You’ll want to decide which town to spend the night in – both have plenty of hotels and dining options.

On your way to Ogunquit and Kennebunkport, I also recommend you stop in York , which is just south of Ogunquit.

Aerial view of Nubble Lighthouse on Cape Neddick, Maine.

Notable stops to make in York if you have time :

Nubble Lighthouse on Cape Neddick – the lighthouse itself is not accessible, as it’s on its own little island, but the viewpoint is really great and worth a stop! It only takes a few minutes.
Stonewall Kitchen Flagship Store & Café – This New England brand started in Maine, and is now sold in specialty stores all over the country, but the flagship store has everything, and is really fun! The café is also very good, and a lot of people come here for lunch.
Downtown York – Waterfront scenery, and some cute shops.
The York Cliff Walk – A pedestrian path along the coast with beautiful views.

*If you’re short on time , I would just do Nubble Lighthouse and maybe Stonewall Kitchen, but if you have time, I do recommend the other two stops.

The views along Marginal Way in Ogunquit, Maine, which is one of the best things to do on a Boston to Bar Harbor road trip.

Best Things To See In Ogunquit In A Day :

→ The charming downtown is filled with shops and eateries.

→ Ogunquit Beach , which is one of the best beaches in Maine!

→ Marginal Way , which is a pedestrian walking path along the coastline that connects downtown Ogunquit with the cute Perkins Cove Harbor. This is my personal favorite thing to do in Ogunquit. The trail is easily accessible from downtown, and is just over 1 mile long each way.

→ Perkins Cove – Once you arrive there after walking Marginal Way, there are some really cute shops to explore, and a lovely bridge that makes for fun photos.

Where To Eat In Ogunquit :

Ogunquit Beach Lobster House
Footbridge Lobster in Perkins Cove for a lobster roll!
BeachFire Bar & Grille

Psst! I have an entire guide on things to do in Ogunquit , if you’re looking for more ideas!

Views from the Kennebunkport Bridge in Maine.

Best Things To See In Kennebunkport In A Day :

→ The adorable downtown , which is mainly Dock Square. You’ll find colorful storefronts and great restaurants here.

→ Drive to Cape Porpoise , where you’ll find beautiful coastal New England scenery, and the cute Farm + Table shop .

→ Enjoy the views of the cove from Kennebunkport Bridge (right at Dock Square).

→ Take a coastal walk on Parsons Way .

→ If you have time, head out on a lobster tour with Rugosa .

Where To Eat In Kennebunkport :

Allison’s Restaurant for a great casual meal
Cape Porpoise Lobster Co. for a lobster roll!
Old Vines Wine Bar

Day 3: Drive To Portland & Make Your Way To Camden

Portland Head Light is the oldest lighthouse in Maine, and one of the best to see on your road trip. It's also one of the best things to do in New England!

This day ends in the beautiful coastal town of Camden, but you’ll be making some fun stops along the way! You can make this day easy by just driving to Portland, and then driving straight to Camden, or you can make it longer and more adventurous by making as many stops you as you feel like. Take a look at all my suggestions, and plan according to your preferences 😊

Option to add a night in Portland : The reason I have you scheduled to only stop in Portland for the day is because it’s such a short drive from Kennebunkport and Ogunquit, and personally, I think the scenery around the Camden area is more quintessential Maine. However, if you have extra time, you can definitely stay the night in Portland, and continue on to Camden the next day!

Things To Do In Portland In A Few Hours :

→ Take a food tour! Portland is a huge foodie destination, and this is a great way to taste your way through the city. The Old Port Seafood Lovers Tour , and Old Port Culinary Walking Tour are both great options.

→ Visit the lighthouses. If you only have time for one, definitely make it Portland Head Lighthouse . This is probably the most iconic lighthouse in New England, and it’s absolutely beautiful. Nearby are also Spring Point Ledge Light , and Bug Light , which are smaller, but still fun to visit. These are all in South Portland, so you’ll want to see them first before getting to downtown Portland.

→ Stroll around Old Port . I suggest parking somewhere around Commercial Street, and then walking around from there. This is the most unique and charming part of the city along the waterfront. Exchange Street and the streets nearby are nice shopping areas, too.

Optional Stops That Are Worth Your Time On The Way To Camden :

Some of these will definitely add time to your trip, so map them out carefully based on your plans to ensure you have enough time in your day.

Marshall Point Lighthouse is one of the best stops to make when driving from Portland to Acadia National Park.

→ Freeport to shop at the L.L. Bean Flagship Campus.

→ Wiscasset – a charming little town with a famous seafood stand called Reds Eats. Also known as being the prettiest village in Maine. You’ll drive right through it on your way to Camden.

→ Pemaquid Lighthouse – a beautiful lighthouse surrounded by dramatic coastline and parks. There is a small fee to enter the grounds, and it’s cash only.

→ Moody’s Diner in Waldsboro is right on your way on the righthand side, making it a little too easy to swing in for one of their famous whoopie pies! It even made my list of the best whoopie pies in Maine .

→ Marshall Point Lighthouse in Port Clyde. This famous lighthouse was featured in the movie Forrest Gump , and it’s such a beautiful area to visit. This is the lighthouse in my homepage photo!

→ Owls Head is a small town that’s not too far of a detour, and is home to Owls Head Lighthouse, and some beautiful coastal scenery. This is one of my top, most favorite lighthouses in New England.

→ Rockland is a charming little coastal town with a great Main Street for shopping. Also home to Rockland Breakwater Lighthouse.

Note s: You’ll pass by Boothbay Harbor on this portion of the drive, but don’t worry! You’ll be stopping there for a night on the way back 😉 You can also make some of these stops on Day 6 of this itinerary when you drive from Bar Harbor to Boothbay Harbor .

You’ll want to arrive in Camden around dinnertime, so you can get settled into your hotel, and then explore the town a bit before sunset.

The waterfront path around Camden, Maine's harbor, which is one of the best places to see on a Boston to Bar Harbor, Maine road trip.

Best Things To Do In Camden :

→ Head out on a sunset windjammer tour!

→ Walk around the harbor to enjoy the idyllic waterfront scenery. Also walk over to the Bay Road Overlook (comes up in Google Maps) for the perfect view of the harbor backdropped by the mountains.

The sailboats docked in Camden, Maine's harbor are always impressive.

→ Grab dinner at a fabulous restaurant . Some of my favorites are Natalie’s, The Waterfront (yep, that’s the name 😊), and Franny’s Bistro.

→ Get some ice cream for dessert at River Ducks or Camden Cone.

→ Drive the auto road in Camden Hills State Park to the top of Mt. Battie and enjoy the bird’s-eye views of the harbor. This road is only open seasonally, but usually only closed in the winter.

→ Shop the lovely boutiques on Main Street and Bay View.

Day 4: Spend The Morning In Camden & Then Drive To Bar Harbor

Refer to the section above for ideas on things to do in Camden the next day. If you weren’t able to take a sailing tour the night before, I do highly suggest booking one for the next day before you leave – this is one of the best places in Maine for a sailing tour!

⛵︎ Here is the Camden sailing tour I recommend: Windjammer Classic Day Sail

Then, make the drive directly to Bar Harbor. On the way, you’ll cross the Penobscot Narrows Bridge , which is one of only four bridge observatories in the entire world! If you have time, it’s worth a stop to enjoy the views from the observatory. Click here for information and fees for exploring the bridge . But it is completely free to drive over if you’re just passing by.

Things To Do Your First Night In Bar Harbor :

→ Walk around the adorable town .

→ Enjoy sunset from Shore Path right in town , with is a coastal walkway.

→ Grab dinner out . I love Geddy’s, Side Street Café, and the Happy Clam Shack for lobster rolls if you’re up for a short drive outside of town.

→ If you have the time, you could also drive up Cadillac Mountain for sunset. While it’s famous for being one of the first sunrises in the U.S., I also love sunset on a clear night and it’s usually less crowded. Note that this requires advanced planning and reservations late May – October.

Sunset at the Cadillac Mountain summit in Acadia National Park.

Day 5: Explore Acadia National Park

Today’s THE day – Acadia National Park! Known as the “Crown Jewel” of New England, the park spans over 70 acres on Mount Desert Island, and offers some of the most iconic and famous scenery in the region.

Best Things To Do In One Day In Acadia :

Park Loop Road in Acadia National Park in Maine.

→ Start with sunrise at the top of Cadillac Mountain . You can also save this for the following morning. Depending on the time of year, you may have to wake up very early for this, so it’s definitely not for everyone. But if it works with your schedule, I do think it’s worth it. It’s one of the most popular activities in the park for a reason!

Note : Reservations are required late May – October to drive the auto road to the Cadillac Mountain summit . They release 30% of the available reservations 90 days in advance, and 70% of them two days in advance. I recommend setting yourself a reminder to check the weather two days in advance, and if it’s forecasted to be a clear day, making the reservation if this interests you. That way, it’s worth it! If it’s forecasted to be cloudy and foggy, the views won’t be a great. Click here for reservation info .

→ Drive Park Loop Road , which is one of the most scenic roads in the park that offers so much for little effort. Along this road, you can make stops at Sand Beach, walk the Ocean Path, visit Thunder Hole, and see the Otter Cliffs. Of all these, I recommend parking at Sand Beach and walking Ocean Path to Otter Cliffs and back. It’s flat and easy, and passes by the best views in the park!

→ Lunch at Jordan Pond House . Famous for their popovers and incredible views overlooking Jordan Pond, this is such a fun thing to do in the park. If the weather is forecasted to be nice, I recommend making reservations for outside if you can. They also have a take out café if you want a quicker experience.

Views along Ocean Road in Acadia National Park.

→ Take a hike, of course! Some easier to moderate hikes in the park that I love are Great Head, Bubble Rock, and Gorham. If you’re looking for an adventurous hike that’s more challenging, Beehive is the most popular in the park. Great Head is especially nice because you start the trail at Sand Beach, and it offers spectacular views of the coastline. And then you can just leave you car in the parking lot and walk Ocean Path.

→ Head to Bass Harbor Lighthouse for sunset . It’s about 30 minutes from Bar Harbor, but on a nice night, sunset here is really beautiful. You’ll need to climb out onto the coastal rocks to see the lighthouse, and parking fills up fast. But if you come prepared with sturdy footwear and arrive early enough, it’s wonderful!

Bass Harbor Lighthouse in Acadia National Park in Maine.

→ If you don’t feel like driving to Bass Harbor Light, I would head back to Bar Harbor to relax and enjoy your last night in town with a dinner out.

→ You can also try to make a reservation for sunset on top of Cadillac Mountain in the park if you weren’t able to go for sunrise!

Views from the top of Cadillac Mountain, which should definitely be on your Boston to Bar Harbor road trip itinerary.

Psst! I have some more detailed posts on Acadia, including my Perfect Acadia National Park Itinerary , Best Places & Towns To Stay When Visiting Acadia National Park , and the Best Time To Visit Acadia National Park .

Day 6: Drive To Boothbay Harbor

You have the option to start your day with a sunrise on Cadillac Mountain if you weren’t able to plan it the day prior! If you do, I suggest having breakfast at Jeannie’s Great Maine Breakfast in Bar Harbor afterward before heading out. They usually open early in-season for everyone getting up to see the sunrise ☀️

The drive to Boothbay Harbor is about 2 hours and 45 minutes without stops, and you also have the option to take the more scenic route and visit some of the suggested stops I detailed in the Day 3 portion of this itinerary. I would go back and reference those if you want to break up the drive.

Why do I recommend the night in Boothbay Harbor? Well, I just love this little coastal town because of its charm, beautiful scenery, slower pace, and all the amazing boat tour options. From Boothbay Harbor, you can take a boat tour out to a puffin colony, head out on a Schooner, or take a lobster trap haul and lighthouse scenic tour. After exploring Acadia the day prior, it’s nice to stop in a town that forces you to slow down a bit, too.

Views from the footbridge, which is one of the best things to see and do in Boothbay Harbor, Maine, and one of the reasons it makes for a wonderful day trip in New England.

Best Things To Do In Boothbay Harbor :

→ Take a boat tour! In addition to Camden, this is another one of the best places in Maine for some kind of tour out on the water just because of how many different kinds are offered. Plus, the scenery around this area is absolutely beautiful.

The lobster trap and lighthouse tour in Boothbay Harbor.

These are the top tours I recommend in Boothbay Harbor: ✓ Schooner Day Sail ✓ Schooner Sunset Sail ✓ Lobster Haul, Lighthouses & Seals Tour

→ Cabbage Island Clambakes! This is SUCH a cool, unique, and authentic Maine experience for dinner. You’ll take a boat from downtown, and be brought to the family’s private island for a traditional New England style clam bake dinner, which includes their famous blueberry cake and gorgeous waterfront scenery. Advanced reservations required.

→ Coastal Maine Botanical Gardens . Located just outside of the downtown area, this is such a beautiful place to explore. Don’t forget to snap your photo with the giant wood troll sculptures!

→ Explore the cute and colorful downtown area .

→ Walk the footbridge , which connects both sides of the harbor.

→ Grab ice cream from Downeast Ice Cream , which is one of my favorites in New England.

Downtown Boothbay Harbor is such a fun stop to add to your Boston to Bar Harbor road trip itinerary.

Where To Eat In Boothbay Harbor :

Boathouse Bistro
Boothbay Lobster Wharf
Shannon’s Unshelled
Robinson’s Wharf in the neighboring town of Southport is also worth it!

Psst! I have a post all about things to do in Boothbay Harbor , if you want some more ideas 😉

Day 7: Drive To Portsmouth & The Essex Coastal Scenic Byway

Portsmouth, New Hampshire is one of the best towns to stop in when driving Boston to Maine.

Making your way back to Boston, there are so many wonderful places you can stop on the way! In fact, it’ll be hard to choose because there’s a lot you can pack in on this portion of the drive, especially along the Essex Coastal Scenic Byway in Massachusetts.

Customize this day how you’d like, but if you’re feeling ambitious and you have enough daylight hours in your day, you can see Portsmouth, and all the best towns in the along the Scenic Byway.

Things To Do In Portsmouth In A Few Hours : Portsmouth is very walkable and compact, so you can see the highlights, even with just an hour or two!

→ Market Square , which is the main shopping area downtown. You’ll find lots of great boutiques and eateries in this section of town.

→ Walk down a cute alleyway to Elephantine Bakery for a coffee and a sweet treat.

→ Walk over to Prescott Park for lovely waterfront views and a garden.

→ Visit the Strawbery Banke Museum to see history come to life (open seasonally). If you don’t go to the museum, definitely walk around this area because you’ll see lots of historic houses nearby.

Once you’re done in Portsmouth, take a 30 minute drive to Newburyport and explore there for a bit. This is where I recommend starting the Coastal Byway drive. Follow the Byway through Ipswich, Rockport, Glouster, Manchester By The Sea, and Salem (which is just outside of Boston).

These are the best stops to make along the Essex Coastal Scenic Byway :

→ Newburyport : One of my favorite places to visit in New England, it’s home to amazing shops and such a charming downtown area that sits on the waterfront. Allow about an hour to walk around, grab lattes and whoopie pies from Chococoa Café, and explore the shops.

Psst! I have an entire guide on things to do in Newburyport, MA & Plum Island if you need more info!

The waterfront part is one of the best things to see in Newburyport.

→ Crane Estate & Crane Beach in Ipswich . This historic estate is so stunningly beautiful, and the beach nearby is the best on the North Shore. Each requires separate admission fees, and you’ll want to budget your time wisely.

Crane Beach in Ipswich, Massachusetts is such a wonderfully scenic place to see along the North Shore.

→ Rockport : One of my all-time favorite coastal towns in New England, Rockport is probably the one place I recommend you don’t miss on the drive. It’s very small, but offers an authentic New England fishing village atmosphere with colorful storefronts, lovely art galleries, great dining, and the most painted building in the country – Motif 1 (which was also featured in the movie The Proposal ).

Psst! I have an entire guide on things to do in Rockport, MA if you need more ideas!

Motif 1 in Rockport, MA, which is a great stop to make when driving from Boston to Bar Harbor.

→ Gloucester is the best place to stop if you have your heart set on a whale watch tour (but you can also take one that departs from Newburyport if that’s more convenient). Whale watch tours in this region are world-class, and head out to the famous Stellwagen Bank National Marine Sanctuary, which is known for its active marine wildlife.

🐋 Click here to check rates & availability for a whale watch tour from Gloucester

Note : While I do love to visit Gloucester, I think with this amount of time, it’s best to focus your itinerary on the other towns along the drive that I’ve recommended, as I think their scenery is more idyllic than Gloucester. Gloucester is also a city, and is bigger and more spread out, so harder to see on limited time. I do recommend it for a whale watch tour, though! If you take the whale watch tour, just know that it will take at least 3 hours, and likely a bit longer.

→ Manchester-By-The-Sea is a beautiful coastal town that can easily be seen in about an hour or so. very picturesque scenery, and it’s home to a lovely beach called Singing Sands.

→ Salem . I’m sure you know it as a top Halloween destination, but it’s honestly great year-round. Filled with historic New England charm, waterfront areas, and some fun places to eat, it’s also very walkable!

Psst! I have an entire guide on taking a Salem, MA day trip and the Best Time To Visit Salem, MA if you want more information for your visit!

State Street in the historic area is one of the prettiest streets to see in Marblehead.

→ Marblehead is such a beautiful town along the North Shore just south of Salem that often gets overlooked, but I absolutely love it here. Also filled with historic charm and lovely waterfront scenery, it’s got a quaint Main Street with some cute shops, a beautiful waterfront park, and some nice places to eat.

Psst! I have an entire guide on things to do in Marblehead, MA if you’re looking for more ideas 😉

More Optional Stops : If you’re looking to explore more of Maine’s coast, there are a few more stops you can make on your way from Boothbay Harbor to Boston. I know, I know – I’m probably tempting you to expand your trip even further, but I’m okay with that 😂

→ Georgetown Island to visit Five Island Lobster Company , which is one of the best lobster rolls in Maine you can get. They’re only open seasonally, and the scenery around there it is very quintessential Maine.

Doubling Point Lighthouse is such a beautiful place to stop on a Boston to Bar Harbor, Maine road trip.

→ The Arrowsic Lighthouses . There are two in this area that I really love: Doubling Point and Squirrel Point. Doubling Point requires a drive down a very bumpy dirt road, and Squirrel Point requires about a 3/4 mile hike through the woods, but they’re both beautiful, small lighthouses on the Kennebec River.

Note : Doubling Point is closed until further notice for repairs. I’m monitoring this and will update once renovations are complete!

→ Bailey Island , which is a very small little island that’s accessible by car, and about a 20-minute detour each way. The best thing to see here is the Giant’s Stairs Trail, which offers beautiful coastal views, and giant rocks you can climb around (just practice caution, of course!). There’s also a cute little place to eat right by the bridge called Sundrenched, which is waterfront and has outdoor seating. This is a nice place to get off-the-beaten-path.

The Giant's Stairs on Bailey Island, which is one of the best New England Islands to visit.

Day 8: Head Back To Boston

It’s the end of your trip! Depending on when you need to make your way back home, or to the airport, you may have some time in the morning to explore a few of the places I mentioned above, but I left this day open in case you have to catch an early flight, or start your drive back home early.

If you do happen to have some time on this day to explore, I would suggest you end the previous day in Rockport, and then explore Salem and Marblehead on this day before heading back to the airport.

Optional Itinerary Adjustments

→ If you have more time and are a city person, I would recommend adding a night to Portland and Boston.

→ If you have extra time and don’t want to add a night to a city, I have two suggestions. First option : add a night to Camden to spend a day exploring the nearby attractions (lighthouses, Rockland, etc.) to make the drive from Portland to Camden easier. Second option : add a night to Bar Harbor to see more of the park, and enjoy more hiking.

→ If you have even longer, you could make this a 2-week adventure by driving up the coast of Maine to Lubec, and then crossing the Canada border to the charming town of St. Andrews by the Sea, and Campobello Island. You could also take the CAT ferry from Bar Harbor to Nova Scotia.

I have a detailed guide on visiting Lubec, Maine , if you wanted to explore places further north!

Best Towns To Stay In On The Drive

For an overnight stay, these are my suggestions on the best places to stay based on experience when it comes to options for dining and accommodations (plus, lovely scenery, of course!). You’ll just want to pick where you stay based on how far you want to drive each day.

As you saw in my itinerary, I included some suggestions for overnight stops, but you may want to customize this trip to your liking (which I encourage!), so I wanted to provide you with more options. It’s also good to know that you won’t have time to stay overnight in all these places unless you extend your trip, but you will be able to, at the very least, drive through them all.

→ Rockport, MA : Not far from Boston, and if you’re looking get a leisurely start or slow-burn end to your trip, I really love to recommend a stay in Rockport. Most everything is pretty walkable, with cool shopping, nice hotel options, and idyllic scenery.

Where To Stay In Rockport : ✓ The Cove at Rockport ✓ Addison Choate Boutique Hotel

→ Portsmouth, NH : As mentioned, fantastic dining and shopping, with lots to keep you busy in the evening after you arrive! Plus, the historic charm is really quite lovely.

Where To Stay In Portsmouth : ✓ The Hotel Portsmouth ✓ Hotel Thaxter

→ Kennebunkport OR Ogunquit : Both of these charming coastal towns that are very close to on another, and both make for a great overnight stay. Kennebunkport has more options for nicer accommodations, but Ogunquit has a gorgeous beach. Both have very charming downtowns that are easily walkable with lots of places to eat and shop! Just pick based on what vibe you’re going for: beachy or just traditional coastal.

Where To Stay In Kennebunkport : ✓ Captains Collection Historic Inns ✓ The Boathouse

Where To Stay In Ogunquit : ✓ Anchorage By The Sea ✓ Cliff House : Technically in York, but a short 10-minute drive to Ogunquit. I like to suggest it because it’s a fantastic resort with amazing coastal views, and worth the splurge! It also makes my list of the top New England resorts and spas 😉

→ Boothbay Harbor : I love stopping here for a night or two every time I make this drive. It’s very small and easily seen in a few hours, and I like to stay the night so I have the option to take a boat tour. I also find the shops and restaurants really great.

Where To Stay In Boothbay Harbor : ✓ Harborage Inn On The Waterfront ✓ Spruce Point Inn

→ Camden : Lastly, I think Camden is the best place to stay before reaching Bar Harbor. Built around a gorgeous harbor, the coastal scenery here is beautiful, and it’s a known sailing destination. There’s also a great Main Street for shopping and dining.

Where To Stay In Camden : ✓ Camden Harbour Inn ✓ Lord Camden Inn

Where To See Fall Foliage Between Boston & Bar Harbor

Manchester By The Sea in the fall season.

If you happen to be planning your trip to coincide with fall foliage, then I would love for you to consider adjusting the itinerary slightly (but don’t worry, it’s not too different!). Most places already on the itinerary offer amazing foliage color. Here are some suggestions to keep in mind:

→ The Essex Coastal Byway in Massachusetts is GORGEOUS in the fall with lots of foliage color. I’ve done this drive during peak foliage, and I was shocked at how beautiful it was. Manchester-By-The-Sea, Essex, Salem, and Newburyport are especially beautiful in the fall. And, of course, Salem is famous for its October festivities!

→ Portsmouth offers some really lovely fall foliage during this time of the year. It’s also an especially cozy place to visit because of all the historic New England architecture.

→ Boothbay Harbor is also amazing in the fall, and the entire harbor is surrounded in fall color. Head out on a boat tour to see even more beautiful fall foliage! Tours usually end around mid-October, so there are typically opportunities that coincide with peak foliage.

The view from the top of Mount Battie in Camden in the fall, which is one of the best stops to make when driving from Boston to Bar Harbor, Maine.

→ Camden is also spectacular in the fall . I definitely recommend hiking or driving up the Mt. Battie Auto Road to take in the views of the harbor from above. It’s the best during foliage season!

→ Kennebunkport also offers some beautiful fall foliage. Having been in October a few times, the fall season always impresses me in this coastal town.

Kennebunkport fall foliage in late October.

→ Of course, the starting and end points on this road trip are stand-outs in the fall, too. Acadia National Park is stunning in the fall season with foliage color, and Boston is also amazing this time of the year. Although, it’s good to know that Boston tends to peak later in October, so in the fall, you may want to plan to spend more time in Boston at the end of your trip to get a glimpse of some foliage color.

What To Pack For This Road Trip

This will depend entirely on what time of year you visit, so plan accordingly based on the season when it comes to clothing and footwear. Beyond that, here are some things I recommend you bring regardless of what time of year you visit.

→ Light sweater or jacket – even in the summer! If you plan to take any boat tours or get up for sunrise at Cadillac Mountain, you’ll want this to stay warm.

→ Reusable water bottle to stay hydrated.

→ Dramamine if you plan to hop on a boat tour and tend to get seasick.

→ Comfortable shoes – I know this seems obvious, but you can leave your fancy shoes at home. I usually wear a really comfortable pair of sandals in the summer, or sneakers in the spring/fall. If you take a boat tour, they may have some requirements on the type of footwear you wear, so double check that, too.

→ Hiking boots if you plan to tackle any trails in Acadia. You’ll be happy to have the ankle support.

→ Camera, of course! You’re going to see so much incredible scenery on this trip, you’ll want to capture the best memories along the way. This is a good trip to get a tripod if you don’t have one – they even make inexpensive ones for iPhones that are perfect for just about anyone.

Tips For This Road Trip

→ Offline maps on your GPS! You’ll have cell phone service in most places, but when you’re near a beach or inside Acadia National Park, you may lose service.

→ Be ready to pay tolls on the roads . Many highways in New England require tolls to be paid, but most have transitioned to an electronic tolling system. This means you’ll likely cruise right through, and your license plate will be billed if you’re not local, and don’t have EZ Pass. If you’re renting a car, you can ask your rental company how they handle this, but they will more than likely charge your card on file after you return it for the tolls you incurred on the trip. This is pretty standard, and makes everything very easy.

→ Bring Some Cash – I know this seems obvious, but as someone who never carries around cash, I’m always reminded when I make this road trip that some places still don’t take credit cards! Usually places like ice cream stands and seafood shacks are the ones that may be cash only, so it’s good to have a small amount on you at all times. Better yet, get a debit card that reimburses you for ATM fees, like the Charles Schwab checking card. Most places will take cards, though.

→ Prepare for crowds at popular places . Depending on the time of year you take this trip, most places will bring in some level of crowds. The most popular destination is Bar Harbor and Acadia National Park, and this is where you can expect the biggest crowds. If you travel in spring or fall, you’ll see fewer people, but places will still be lively.

→ Prepare for the cost . New England in general is just an expensive region to visit, unfortunately, and prices tend to be higher than other parts of the country.

→ Always be respectful of private property , and never trespass to get the perfect photo. The same goes for not putting yourself or others in danger to get a photo. For example, if you see a beautiful photo spot along a main road, and there’s no place to safely pull over, don’t risk it. There are so many beautiful nooks and crannies around New England that I guarantee you’ll stumble upon a picturesque spot that’s safe to photograph rather often 😉

Looking to expand this road trip into Canada? I’ve got you covered – ✓ My Guide On Traveling Between Bar Harbor, Maine & Nova Scotia ✓ My Maine To Canada Itinerary: A DREAMY East Coast Road Trip

That’s A Wrap On My Boston To Bar Harbor, Maine Road Trip!

And there you have it! After years of perfecting it, I’m thrilled to finally share my unforgettable Boston to Bar Harbor, Maine road trip itinerary with you. I truly believe that the New England coast is such a special and memorable region to experience for yourself, and with this guide, you’ll see the very best it has to offer. Happy planning!

You might also enjoy

Lubec Maine is worth visiting just to see West Quoddy Lighthouse.

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The Perfect 7-Day New England Road Trip from Boston 2024

Planning a 7-day New England road trip itinerary from Boston?

Ah, New England. I have long been smitten with this historic region of the country, which includes Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

Now that I’ve lived in New England for five years, I have a better understanding of the BEST places to see if you’re visiting for a short time.

Once you arrive in New England, you will likely wish you could stay much longer than 7 days. However, there are several highlight spots you can reach in one week to get a good taste of the region. That’s the list I have curated for you in this 7-day New England road trip itinerary!

⏰ SHORT ON TIME? 🛌 DESTINATIONS + WHERE TO STAY Boston, Massachusetts: Hyatt Regency Boston Harbor Newport, Rhode Island: Hotel Viking Mystic to Washington, Connecticut: Mayflower Inn & Spa Stockbridge, Massachusetts to Killington, Vermont: Mountain Meadows Lodge Stowe, Vermont: Trapp Family Lodge White Mountains, New Hampshire: New England Inn & Lodge Portland, Maine and Portsmouth, New Hampshire: Hampton Inn & Suites 🚗 NEED A CAR? Book through Discover Cars for some of the best rates

New England Road Trip for 7 Days

This road trip is a loop that begins and ends in Boston, Massachusetts, the largest city in New England. If you plan to fly to New England and rent a car there, you can usually find the best flight deals into Boston.

From Boston, you’ll travel south to Rhode Island and Connecticut, north through western Massachusetts and into Vermont, northeast into New Hampshire and Maine, and then back down to Boston.

Day 1: Boston, Massachusetts

Kick off your 7-day New England itinerary with a tour of Boston. Explore North End , Boston’s Little Italy, to taste authentic Italian food, and then begin walking along the historic Freedom Trail by Old North Church .

Stop by Faneuil Hall Marketplace , known as the Cradle of Liberty because patriots would meet here in the days leading up to the Revolutionary War. Not far from Faneuil Hall you can also see Boston’s Old State House, Old South Meeting House , and the Benjamin Franklin statue.

Have lunch in Boston’s Chinatown , a center of Asian-American life in New England. Then walk over to Copley Square and explore the beautiful Boston Public Library (don’t miss Bates Hall!).

Browse the shops along Newbury Street before walking the Charles River Esplanade for scenic city views. End your day in Boston by exploring the picturesque cobblestone streets of Beacon Hill and walking through Boston Common and the Public Garden .

🇺🇸 For a fun way to learn about the history of Boston, check out this popular walking tour with an emphasis on storytelling .

7-day New England road trip: Beacon Hill, Boston

➡️ See my 24 hours in Boston post for a more detailed list of things to do in Boston in a day, along with a sample route map.

Where to Stay in Boston

📍 Hyatt Regency Boston Harbor : Mid-range hotel with great views of the Boston Harbor.

📍 Omni Parker House : One of Boston’s most iconic and historic hotels, in operation since 1855.

Day 2: Newport, Rhode Island

Only 1.5 hours south of Boston is the beloved coastal town of Newport, Rhode Island . It’s my husband and my favorite place in Rhode Island and one we never get tired of visiting.

The best thing to do in Newport is walk the scenic Cliff Walk , a 3.5-mile scenic trail with stunning views of the Atlantic Ocean almost the entire way. While you’re near the Cliff Walk, it’s also worth stopping by one of the iconic Newport mansions for a tour. The most famous of the mansions is The Breakers .

Book this five-star-rated Newport trolley tour for an easy way to tour the Breakers and see other key sites in Newport. ⭐️⭐️⭐️⭐️⭐️

Downtown Newport, especially Thames Street, is bustling with shops and restaurants within traditional New England architecture. The Red Parrot restaurant has delicious fish and chips, but if you want to visit the oldest operating restaurant in the U.S., go to White Horse Tavern .

🦀 Want to experience more of Newport’s food scene? Check out this highly-rated food and history walking tour .

After that, it’s worth stopping by Kilwins for ice cream and enjoying it on a bench in Queen Anne Square while looking out at Newport Harbor .

If you have time to spare, hop on the Newport Harbor Shuttle to Fort Adams State Park and take a walk around the old fort for beautiful water views.

Queen Anne Square, Newport, Rhode Island

Where to Stay in Newport

📍 America’s Cup Inn : A small hotel within easy walking distance of most downtown Newport attractions. Each room is uniquely decorated with antique, colonial furnishings.

📍 Hotel Viking : On the list of Historic Hotels of America, this hotel is full of character and charm.

Day 3: Mystic to Washington, Connecticut

On day 3 of this 7-day New England road trip, you will head one hour west to the moody port town of Mystic —one of Connecticut’s most beautiful places .

Here you will find one of the largest maritime museums in the United States, Mystic Seaport, as well as the oldest merchant vessel in the U.S., the Charles W. Morgan whaleship.

The main street of Mystic has several cute boutique shops and restaurants. If you’re craving seafood, you might enjoy The Mariner for a tasty lunch. Their menu ranges from oysters and clams to fish and lobster.

7-day New England road trip: Mystic, Connecticut

If you’re a book lover, it’s worth visiting the Book Barn in Niantic for an hour or two. It’s one of the largest used booksellers in New England with more than 500,000 books, and it’s only about a 25-minute drive west of Mystic.

From there, you will drive about 1.5 hours northwest to the charming town of Washington, Connecticut .

Park near the old post office, which is now the popular Po Cafe serving delicious food and drinks. (Note they are only open until 2 p.m. and are closed on Sunday and Monday, so I suggest coming here for breakfast on Day 4.)

Not far from the cafe, you can walk past the picturesque First Congregational Church , a large white-steepled church typical of New England, and then stroll through the quiet neighborhoods with their quaint, well-landscaped homes.

First Congregational Church in Washington, Connecticut

Where to Stay in Washington

📍 A Whimsical Cottage : This cozy vacation home will give you a more local experience of Washington.

📍 Mayflower Inn & Spa : If you’re a Gilmore Girls fan, this luxurious hotel will be especially meaningful, as it’s said to have inspired the Independence Inn on the show.

Day 4: Stockbridge, Massachusetts to Killington, Vermont

Start your day with breakfast at the Po Cafe in Washington before heading north to the historic town of Stockbridge, Massachusetts , located in the scenic Berkshires highlands.

Inside the old Stockbridge General Store building is Main Street Cafe , which still maintains a lot of the original interior. The old general store was made famous in one of Norman Rockwell’s paintings.

Historic Main Street in Stockbridge, Massachusetts

Speaking of Norman Rockwell, the Norman Rockwell Museum is also located in Stockbridge, if you want to see some of the original artwork from the iconic American painter.

After spending some time in Stockbridge, you’ll continue driving a little over two hours north into the lush Green Mountains of Vermont.

If you’re up for a hike after all that driving, you could do the moderate 2-mile out-and-back Deer Leap Overlook Trail near Killington, which takes just over an hour to complete.

Finish the day with a hearty dinner at Casey’s Caboose or The Garlic , both located in Killington.

Where to Stay in Killington

📍 Mountain Meadows Lodge : Cozy rooms and delicious breakfast, with gorgeous mountain views.

📍 The Snowed Inn : Close to Killington ski resort, this hotel has a year-round outdoor hot tub.

Day 5: Stowe, Vermont

On day 5 of this 7-day New England road trip, you will visit the magical town of Stowe, Vermont .

About an hour and 20 minutes north of Killington, Stowe is known as the birthplace of alpine skiing in Vermont. Its first lift-operated ski run began in 1937 on Mount Mansfield (the tallest point in Vermont at 4,939 feet).

However, Stowe is great to visit any time of the year. In the fall, tourists flock here for some of the best fall foliage vistas in New England. Spring is the perfect time to go on a maple syrup tour to learn how Vermont’s famous sugary goodness is made.

In the fall, spring or summer, enjoy one of Stowe’s many hiking and biking trails or kayak along the Winooski or Lamoille Rivers .

Scenic Vermont in the fall, 7-day New England Road Trip

Best hiking trails in Stowe

Stowe Pinnacle via Pinnacle Meadow Trail (Moderate): This 3.2-mile out-and-back trail takes about two hours to complete and connects with the popular—but more challenging—Stowe Pinnacle Trail that leads up to Stowe Pinnacle.
Bingham Falls Trail (Easy): This 0.5-mile out-and-back trail only takes about 20 minutes to complete and provides lovely views of Bingham Falls at the end. People have commented that the rocks can get slippery near the bottom, so be careful!
Stowe Recreation Path (Easy): This paved 5.5-mile, out-and-back greenway is great for bikes and strollers. There are numerous shops and restaurants along the path where you can stop to browse or grab a bite to eat.

Other things to do in Stowe

Visit Moss Glen Falls located along the scenic VT 100 highway.
Tour Smugglers Notch State Park and drive the VT 108 highway.

Where to Stay in Stowe

📍 Green Mountain Inn : Rooms decorated in handcrafted Vermont furnishings, located in the center of historic Stowe.

📍 Trapp Family Lodge : Austrian-inspired architecture and furnishings with gorgeous mountain views.

Day 6: White Mountains, New Hampshire

Now that you’ve experienced the Green Mountains of Vermont, drive a couple hours east to the White Mountains of New Hampshire .

Start in the small town of Lincoln, where you will find the beginning of the famous Kancamagus Highway , a scenic 34.5-mile drive through White Mountain National Forest. There are numerous stops along the highway for stunning outlooks and hiking trails:

Lincoln Woods Trail: This is one of the first stops along the Kancamagus Highway. Walk the suspension bridge over the rocky Pemigewasset River and you’ll end up on a leisurely out-and-back trail along the river with towering trees overhead.
CL Graham Wangan Overlook: From this point, you will have one of the prettiest views of the Swift River Watershed and White Mountain peaks in the distance.
Sabbaday Falls: A short hike will lead you to this beautiful waterfall, which has a guardrail on one side for you to stand and see the falls up close. There is a picnic area nearby, making for a picturesque spot to enjoy lunch.
Sugar Hill Overlook: This is one of the most popular viewpoints along the Kancamagus Highway, where you can see the Swift River Valley and surrounding mountains.
Rocky Gorge: Take the small footbridge across the gorge for scenic views of the Swift River.
Albany Covered Bridge: See one of New England’s traditional covered bridges right along the Kancamagus Highway.

The Kancamagus Highway ends near North Conway, where you can enjoy a laid-back, all-American meal at the highly-rated Muddy Moose Restaurant & Pub or Delaney’s Hole in the Wall .

Walking the Lincoln Woods Trail in the White Mountains of New Hampshire

Where to Stay in North Conway

📍 New England Inn & Lodge : Comfortable and cozy rooms in a wood cabin-style hotel.

📍 White Mountain Hotel & Resort : Features a heated pool and hot tub overlooking the mountains.

Day 7: Portland, Maine and Portsmouth, New Hampshire

On the last day of this 7-day New England road trip, head 1.5 hours southeast to the iconic coastal town of Portland, Maine . Here you will see a blend of traditional New England architecture and history, along with contemporary, artsy vibes.

Visit Bug Light Park to see the beloved Bug Light, standing at only 26 feet tall, and walk along the scenic Eastern Promenade for stunning views of Casco Bay.

7-day New England road trip: Downtown Portland, Maine

Take a ride on the historic Maine Narrow Gauge Railroad , and snag some fresh seafood from the Portland Farmer’s Market (open Wednesdays and Saturdays) or Harbor Fish Market .

The #1 thing to do in Portland is visit America’s most photographed lighthouse, Portland Head Light , located on Cape Elizabeth. Not only is the lighthouse itself beautiful, but the surrounding landscape will take your breath away.

7-day New England Road Trip: Portland Head Light on Cape Elizabeth, Maine

The very last stop on this 7-day New England road trip is Portsmouth, New Hampshire , another picture-perfect town about an hour from Cape Elizabeth.

Park downtown and browse the shops and boutiques along Congress Street. For dinner, I highly recommend The Flatbread Company , which makes delicious wood-fired pizza with locally sourced ingredients.

7-day New England Road Trip: Downtown Portsmouth, New Hampshire

Where to Stay in or near Portsmouth

📍 Hampton Inn & Suites : Centrally located in Portsmouth with breakfast included, this hotel is a short walking distance from restaurants and other town attractions.

📍 Wentworth by the Sea : Located in New Castle, just outside of Portsmouth, this dreamy hotel offers cozy rooms with stunning harbor views. I’ve stayed here a couple of times and absolutely loved it.

New Castle is less than an hour from Boston, where you can return on Day 8 to end your epic New England road trip!

New England 7-Day Road Trip Map

More Places to Add to Your Itinerary

If you want to extend your trip beyond a week (I would not blame you one bit), here are a few other places to add to your itinerary!

Acadia National Park, Maine

The crown jewel of the North Atlantic coast, Acadia National Park is an absolute must-see. I didn’t include it in this 7-day New England itinerary because it’s a bit too far north, but if you have a few more days to spare, you won’t regret a visit here.

Reserve a time slot on Recreation.gov to take in the mesmerizing views at the summit of Cadillac Mountain (note the Cadillac Mountain Summit Road is only open from around April to October).

Relax on one of Maine’s only sandy beaches, aptly named “ Sand Beach ” and walk along the jagged coastline on the Ocean Path Trail .

Hike around Jordan’s Pond and try the famous tea and popovers at Jordan’s Pond House Restaurant .

And of course, you must pay a visit to the picturesque town of Bar Harbor , right next to Acadia National Park. Jordan’s Restaurant is known for its amazing blueberry pancakes, and Mount Desert Island Ice Cream serves some of the most interesting flavors.

View from Cadillac Mountain in Acadia National Park, Maine

How to incorporate Acadia National Park into your New England itinerary:

Acadia National Park would naturally fit after Day 6 in this itinerary, but you would want to give yourself at least three extra days to drive up there and fully explore the region before heading south to Portland.

Ogunquit, Maine

Ogunquit is a popular destination here in New England but not as well-known in other parts of the USA. It’s one of the first towns after crossing the border into Maine, and it has a lot of fun things to do.

Ogunquit Beach Lobster House : Not far from Ogunquit Beach, this restaurant serves amazing seafood. This is the place where I first fell in love with lobster rolls.
Ogunquit Beach: This family-friendly beach is especially popular in the summer as it’s a large beach and there are many shops and restaurants nearby.
Perkins Cove: Browse through this cluster of shops and restaurants in traditional New England architecture. Be sure to stop at the Corner Cafe for delicious Maine blueberry pie ice cream!
Marginal Way: Near Perkins Cove is Marginal Way, a 1.25-mile trail with ocean panoramas the entire way. It gives the Cliff Walk in Newport, RI a run for its money.

Enjoying Maine blueberry pie ice cream at Perkins Cove in Ogunquit, Maine

How to incorporate Ogunquit into your New England itinerary:

You could swap Portsmouth, NH with Ogunquit, ME on Day 7 and visit Portsmouth on Day 8, OR dedicate an entire day to Portland, ME and spend Day 8 in Ogunquit and Portsmouth.

Salem, Massachusetts

Salem is best known as the location of the Salem Witch Trials in 1692. If you are curious about the town’s dark past, visit the Salem Witch Museum , Salem Witch Trials Memorial , and Old Burying Point Cemetery . Unsurprisingly, Salem is especially popular to visit during the Halloween season.

The House of Seven Gables , made famous by Nathaniel Hawthorne’s 1861 novel with the same name, is also located in Salem and worth a tour.

How to incorporate Salem into your New England itinerary:

Stay an extra day in Boston and visit Salem as a day trip. Salem is only about 25 miles north of Boston.

Cape Cod, Massachusetts

For beautiful New England architecture, bright and blossoming hydrangeas, and some of Massachusetts’ best beaches, visit the state’s iconic curved peninsula, Cape Cod. It’s one of Massachusetts’ most popular destinations, and with good reason.

Cape Cod is busiest in the summer months when New Englanders and out-of-towners flock to the beaches. If swimming isn’t your #1 priority, you might choose to visit in the spring or fall instead.

Coast Guard Beach is one of the best beaches on Cape Cod, but Keyes Memorial Beach is also a good option. If you have time to drive all the way to the tip of Cape Cod, the town of Provincetown is known for its art galleries and delicious restaurants.

Coast Guard Beach on Cape Cod, Massachusetts

How to incorporate Cape Cod into your New England itinerary:

Extend this 7-day itinerary by another day or two (or longer, if you plan to visit Martha’s Vineyard or Nantucket as well!).

Martha’s Vineyard or Nantucket, Massachusetts

In many ways, the iconic islands of Martha’s Vineyard and Nantucket represent what people traditionally associate with New England: wind-weathered, shingled homes, harbors filled with sailboats and seagulls, and quaint shops and restaurants. A visit to one of these islands will make you feel like you escaped to another world.

How to incorporate these islands into your New England itinerary:

I recommend visiting Cape Cod and one or both of the islands at the same time, as one of the best ferry options to the islands departs from Hyannis or Woods Hole on Cape Cod.

The ferry ride from Hyannis to Nantucket is roughly one hour, and from Woods Hole to Martha’s Vineyard is about 45 minutes.

Lake Champlain and Burlington, Vermont

Lake Champlain is Vermont and New England’s largest lake, which is also shared with New York and Quebec, Canada. There are plenty of things to do on and around the lake, including boating, kayaking, swimming, shopping, dining, and more.

Burlington is the largest city in Vermont and is nestled right along Lake Champlain. It’s a hip, artsy town with an awesome food and shopping scene.

How to incorporate Lake Champlain into your New England itinerary:

An extra day or two to visit Lake Champlain and Burlington could be sandwiched between Days 5 and 6 in this New England itinerary.

Here are answers to some common questions about New England.

When is the best time to visit New England?

This all depends on what interests you most! New England is beautiful any time of the year, but winter is the most unpredictable in terms of weather. It’s not uncommon for there to be large snow storms that make travel conditions especially difficult.

Unless you are going with the intention of skiing in Stowe and doing other winter activities, you may want to avoid a road trip to New England from December to mid-March.

Do you enjoy exploring in the winter? Check out Massachusetts in Winter: Things to Do, Places to Visit, and More .

Spring is beautiful in New England with all the blossoming trees, but expect a little more rain than usual from March to June. Some hiking trails might still be muddy from the rain and melting snow.

Spring in New England is full of blossoming trees

New England summers are really nice, with warm temperatures that are typically not overbearing and lots of sunny days. July to September is when spending time at the beaches and lakes is the most enjoyable.

Of course, New England attracts lots of tourists in the fall because of the colorful foliage. What’s also great about this time of year is the temperatures are a bit cooler but still pleasant enough for hiking and sightseeing.

When is the best time to see fall foliage?

This can be tricky to say, depending on which part of New England you visit and what the weather is like.

For example, in 2022, we visited the White Mountains of New Hampshire in mid-October and already missed the peak period for colorful foliage . At the same time, the leaves were only just beginning to change color in Boston where we live.

For northern New England states, including Vermont, New Hampshire and Maine, the end of September to the beginning of October will likely be the best time to see the fall colors.

For southern New England, including Massachusetts, Connecticut, and Rhode Island, peak season will likely be a bit later, from the beginning of October to early November .

For some of the best fall foliage sightseeing in New England, check out 10 Best Stops on the Kancamagus Highway, New Hampshire .

Fall in the White Mountains of New Hampshire

How many days do I need in New England?

As you have probably gathered from this post, there is A LOT to see in New England. 🙂 At a minimum, I recommend spending an entire week in this region to get a taste of all six New England states.

However, if you have a little more time to spare, two weeks would allow you to tack on additional destinations not included in this 7-day road trip, such as Cape Cod or Acadia National Park.

Is New England expensive?

This varies based on what time of year you go and what activities you want to do. Generally, costs in New England are a bit higher than other parts of the U.S. but as with any trip, there are ways to spend more money and ways to save.

For example, if you plan to spend the majority of your time hiking and walking outdoors, your trip will not be nearly as expensive as if you book a lot of special tours and activities or often dine in restaurants.

Tourism in New England is highest in the summer and fall, so hotel costs will likely climb during these seasons.

New England is such a historic and beautiful part of the country, with something for everyone to enjoy. To recap, here is a quick summary of this 7-day New England road trip:

Day 3: Mystic, Rhode Island to Washington, Connecticut
Day 7: Portland, Maine to Portsmouth, New Hampshire

If you’ve determined that New England is too awesome to limit your visit to just one week, here are some great add-ons:

Acadia National Park, Maine (between Days 6 and 7)
Ogunquit, Maine (on or after Day 7)
Salem, Massachusetts (between Days 1 and 2 or after Day 7)
Cape Cod, Massachusetts (after Day 7)
Martha’s Vineyard or Nantucket, Massachusetts (after Day 7)
Lake Champlain, Vermont (between Days 5 and 6)

Have a fabulous time!

PLANNING A TRIP? These are the resources I recommend: ✈️ Flights: Skyscanner 🛌 Hotels: Booking.com 🚗 Rental cars: DiscoverCars 🎟 Tours: Viator or GetYourGuide

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17 Best Stops on a Boston to Bar Harbor Road Trip

Last Updated on January 8, 2024

by Maggie Turansky

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

If you’re looking for the quintessential tour of New England, then you cannot go wrong with going on a Boston to Bar Harbor road trip. Driving from the Massachusetts capital to the gateway to Acadia National Park will take you through three states and countless amazing places to visit along the way.

There are plenty of people who plan to make this drive in just one day. And while this is certainly possible, you will be missing out on some of the most charming towns and cool spots that Massachusetts, New Hampshire and Maine have to offer. So whether you want to take in every lighthouse possible or sample lobster rolls while meandering up the Maine coast, this is the guide for you.

Planning your road trip can be a joy of an experience when you consider just how much there is to see and do in a relatively short distance. So if you want to go on the perfect drive through coastal Maine, then make sure to include at least some of these stops.

Table of Contents

Planning a New England Road Trip

Unlike embarking on a road trip in the western USA (for instance, from Seattle to Yellowstone National Park ), the drive from Boston to Bar Harbor is relatively densely populated and you won’t be driving through large patches of open wilderness with services available. Conversely, there are plenty of towns along the way and just as many gas stations and facilities so you don’t need to plan too far in advance.

One thing to keep in mind is the season that you plan to do this road trip in. Obviously, the summer months of June, July and August are the most popular for those driving to Bar Harbor as the weather conditions are the mildest.

There isn’t much you need to consider when it comes to road safety in these months, except to be on the lookout for deer and moose and to be aware that conditions can, at times, get foggy.

Bass Harbor Lighthouse in Acadia National Park

If you’re travelling in the cooler months from as early as late October through April, be aware that snow can be an option. Particularly in the winter months, there will be quite a bit of snow (and, honestly, Acadia may not be the most pleasant to visit then, anyway).

Autumn is another very popular time to visit, namely because the foliage is simply spectacular. Note that the days do start to get shorter and there can be more rain, but driving conditions should still be fine.

Road conditions are generally good, but it always pays to be aware of wildlife!

If you need to rent a car for this road trip, you can browse Rentalcars.com which shows deals across a number of different car rental companies.

How Far is Boston to Bar Harbor?

Without stopping, the Boston to Bar Harbor drive time along the I-95N is about five hours total and the distance between Boston and Bar Harbor is about 300 miles (483 kilometres). However, staying completely on the I-95 isn’t the ideal route to go if you want to make the most out of this road trip.

Instead, getting off the interstate once you’re past Portland and heading north on Highway 1 is going to be far more rewarding, even if it will add to your overall drive time. This is where you will find the majority of the worthwhile stops on the Boston to Acadia road trip and it is certainly the most picturesque, taking you all along the coast.

Though you could do this drive within the span of the day, if you want to make a road trip out of it, it’s worth planning a few nights to get all the way up to Bar Harbor. Planning to stop for a few nights in Portland and in the midcoast town of Camden or Rockland.

Best Boston to Bar Harbor Road Trip Stops

Salem, massachusetts.

Leaving the city, the first stop on the drive is a bit of a detour, but worth it nonetheless – and that is Salem.

The historic seaside town is notable for being home to the Salem Witch Trials – a series of prosecutions of accused witches in 1692-1693, the trials resulted in over thirty guilty convictions which resulted in the hangings of fourteen women and five men. At least five other people died in prison and one man was pressed to death for refusing to plead.

The Salem Witch Trials are obviously an incredibly dark part of this town’s history and you can learn more about them while visiting this town.

However, these days, Salem is also well known for being a hub for the New Age. So if you’re interested in learning about dark Puritanical history and also may want to pick up a deck of tarot cards or get your palm read, then Salem is an excellent stop for you. It’s also a popular day trip from Boston

Portsmouth, New Hampshire

When driving from Boston to Bar Harbor, the stretch that goes through New Hampshire is only about 20 miles, however, that doesn’t mean there isn’t anywhere to stop in this great state!

And the best place to explore on this route is the lovely seaside town of Portsmouth. Not to be confused with the city in Hampshire, England, Portsmouth, New Hampshire is small but charming and very much worth exploring as you make your way to Maine.

If you’re looking for a great place to grab some lunch, then make sure to head to Geno’s Chowder & Sandwich Shop , located right on the harbour. This place has a great deal on a cup of chowder and a fresh lobster roll, so you can start getting your fix before you’ve officially made it to Maine!

Portsmouth’s town centre is also filled with interesting shops to browse and it can be very much worth taking a stroll along the main drags.

If you’re travelling with children, make sure to make a stop at Treehouse Toys, which is an excellent independent toy store that can be a lot of fun for adults, too!

Lobster Roll in Portsmouth, New Hampshire

Cape Neddick, Maine

The next (and subsequent) stop on this road trip from Boston are in the great state of Maine and what could be a more iconic first place to stop than a lighthouse?

And one of the most beautiful lighthouses in Maine happens to be located in the southern town of York on Cape Neddick and that is the beautiful Nubble Lighthouse.

This lighthouse is situated in an absolutely beautiful setting on its own small island. You can view it easily from the mainland while also enjoying the lovely scenery of the waves crashing against the rocky shoreline.

There are also plenty of benches and places to sit around here, so you can spend the time you’d like enjoying the views of this beautiful lighthouse.

Ogunquit, Maine

Only a few miles north of Cape Neddick along the coast of Maine lies the popular tourist town of Ogunquit which is home to, in my opinion, one of the most beautiful beaches in the state.

While the state isn’t necessarily known for having “beach weather,” the few months of the year when it is warm enough to enjoy the white sands, then Ogunquit Beach is an excellent option for this!

Ogunquit is also home to a cute downtown area with plenty of shops along with a lot of other kitschy seaside town mainstays – such as mini-golf!

There are a number of famous lobster shacks to eat at if you have a hankering for seafood. Alternatively, we can recommend eating at the Greenery Cafe , which has an extensive breakfast menu along with plenty of sandwiches and salads for those looking for a great lunch option!

Kennebunkport, Maine

Another very famous seaside town in Southern Maine and a perfect stop on a Boston to Acadia road trip is Kennebunkport. This is another very popular vacation spot and it has a lot to offer visitors.

Of course, like the rest of Maine, lobster shacks and seafood restaurants abound, and there are some lovely beaches to enjoy and a gorgeous harbour and coastal views to take in.

There is also a charming town centre that is filled with interesting shops and other points of interest. There are also a few small museums to take in, should this suit your fancy, And if you’re interested in getting out on the water, there are plenty of options available for you in Kennebunkport.

And if you want to experience another beautiful beach before hitting the next stop, visit Old Orchard Beach – one of the most beautiful in the state.

Cape Elizabeth, Maine

Located directly to the south of Portland (and effectively a suburb of the city), Cape Elizabeth is home to arguably Maine’s most prominent and iconic lighthouse – the Portland Head Light.

Situated in the vast Fort Williams Park, this lighthouse isn’t the only attraction here. Fort Williams Park boasts some beautiful cliffside views and walks, small swimming areas and beaches, an old fort and plenty of beautiful grassy areas to enjoy.

All in all, this makes for an excellent stop in the Portland area before heading into the city proper and exploring the old port, and also gives you an opportunity to take in Maine’s most notable lighthouses!

Portland, Maine

No drive from Boston to Acadia National Park would be complete without a stop in Maine’s largest city, Portland. Though this isn’t a huge city by most metrics (it’s home to only about 70,000 people), this is the largest metropolis in the state and has a lot to offer visitors.

Not only are there fantastic restaurants to enjoy and plenty of locally brewed craft beer to sip, but there are also a number of cool things to see and do that it’s worth spending a couple of days in Portland in order to really get to know this city and to do it justice.

Maine doesn’t have a lot of cities, so it’s a great place to get an “urban” vibe, especially considering how rural and small the rest of the towns on this road trip are!

Freeport, Maine

As the last major stop before you venture off the interstate and onto Highway 1, Freeport is an essential stop on any Maine road trip for one reason – the flagship store of LL Bean.

This shop is absolutely massive and offers anything an outdoor lover could imagine. Set over a number of different areas and across a couple of floors, the LL Bean store is a very “Maine” place to visit.

Known for its massive boot marking the entrance, this is the perfect place to pick up any outdoor gear you may need (or forgot to pack!) for your trip to Acadia National Park.

The town of Freeport itself also has a nice downtown area with several cute shops and cool restaurants to check out, so make sure not to only set your sites on LL Bean and explore a bit of the town, as well!

Wiscasset, Maine

Dubbed “the prettiest village in Maine,” the town of Wiscasset is an excellent stop in the midcoast region on a scenic drive up the coast, especially if you’re feeling a little bit hungry!

Located directly on Highway 1, Wiscasset is perhaps best known for being home to the famous Red’s Lobster Shack , which has been highlighted in a number of different publications over the years.

Because of this, the shack gets queues that wind their way around the corner and up the streets and, in the busy months, you could be waiting to get a lobster roll for hours.

If you want to minimise your wait but still have an incredibly high-quality meal, then head to Sprague’s – located right across the street. They have a similar menu to Red’s, delicious food and they also make incredible milkshakes with the local Giffords Ice Cream! They also have a nice outdoor seating area.

Like most other towns in the area, Wiscasset also has a number of cute shops and things to see and do in the town centre, that is very much worth exploring.

Boothbay Harbor, Maine

This stop is a bit of a detour from Highway 1 and can be a bit of a touristy stop, but if you want to experience a truly charming Maine harbour, then make sure to head to Boothbay while on your Boston to Maine road trip.

Boothbay Harbor is a bit of a kitschy tourist town, but it can be a good place to visit if that is your thing. It’s full of souvenir shops and opportunities to go on harbour cruises and whale-watching tours.

The harbour itself is really lovely and a joy to stroll around and the drive down the peninsula to reach this town is gorgeous, as well.

Damariscotta, Maine

Coastal New England is well known for its oysters but you would be hard-pressed to find a more famous local variety than the Damariscotta oyster – hailing from the eponymous river in this beautiful Maine town! Damariscotta is a small town with a charming main street, home to plenty of local artisan’s shops and a number of great restaurants.

When driving through this region, you will also notice plenty of oyster farms in the river and, if you want to sample some, make sure to head to one of the many oyster bars or restaurants and order a few in any style that you desire!

Waldoboro, Maine

Waldoboro isn’t a stop that makes it onto most Maine road trip itineraries, however, that doesn’t mean that it isn’t worth visiting a few places in this unassuming town! Located on Highway 1, one of the best places to stop in Waldoboro is Moody’s Diner , especially if you’ve got an appetite.

This classic diner has been in business for over 80 years. It’s open daily and serves up diner favourites and also makes dozens of freshly baked pies each day – so even if you’re not hungry enough for a meal, it’s worth stopping by for a slice of pie, at least!

If you’re interested in sampling some locally brewed craft beer, one of our favourite breweries in the region is based in Waldoboro – Odd Alewives Brewery. Located in a refurbished barn on Old Route 1, they have a handful of fantastic beers on tap, a wood-fired oven for delicious pizzas and a delightful garden setting to enjoy.

Rockland, Maine

One of the most popular destinations in Midcoast Maine, this is a can’t-miss stop on your Boston to Acadia drive. There are a number of things to do in Rockland that it can be worth planning to spend a couple of nights in this area so you have enough time to see and do everything there is to offer.

Like many towns in the region, Rockland has a charming downtown filled with art galleries, museums, shops and great restaurants – a personal favourite is North Beacon Oyster!

And if you’re looking for something quick to eat, you cannot go wrong with Wasses Hot Dogs . Rockland is also home to the Maine Lobster Festival, so this is the perfect town to pick up yet another lobster roll.

Make sure to walk out to the Rockland Breakwater Lighthouse also visit the charming lighthouse at nearby Owl’s Head. There is also the opportunity to take a ferry to one of the nearby islands if this suits your fancy.

Rockport, Maine

Located about a ten-minute drive north of Rockland is the small town of Rockport. This town often gets overlooked, with visitors being more taken in by beautiful Camden or bustling Rockland, but Rockport has its own charm and it’s worth stopping in on your way up to the town of Bar Harbor.

Outside of the town centre, you can find the fantastic Oakland Park Lanes , a classic candlepin bowling alley that’s the perfect place to spend a rainy day for young and old alike.

Downtown Rockport has a charming harbour that is arguably prettier than neighbouring Camden. And if you’re looking for a great meal, then make sure to head to 18 Central, located on Rockport’s main drag.

Camden, Maine

Along with Rockland, Camden is probably the most popular place to visit in Midcoast Maine and it’s for a good reason – it is incredibly charming. Located only about eight miles (about a fifteen-minute drive) north of Rockland, there are a number of things to do in Camden that make it a great place to base yourself for a few nights while on your road trip to Bar Harbor.

Camden Harbor is beautiful and you can even opt to take a sailing cruise from here. If you simply want to enjoy the views, then make sure to have a meal at the delicious Waterfront Restaurant. Kids will love the nearby Uncle Willy’s Candy Shoppe — but it is super fun for adults with a sweet tooth, too.

For those looking to get a bit active, then consider going for a hike in the nearby Camden Hills State Park. Either hiking or driving up to Mount Battie – the highest peak in the park – will provide excellent views over Camden Harbor and Penobscot Bay as a whole and there are plenty of other hiking trails to enjoy, as well.

Lincolnville, Maine

Heading north along Highway 1 from Camden, the next major town you will hit is lovely Lincolnville. This little town is pretty small, however, it can be worth a stop – especially if you’re interested in heading to the beach.

Lincolnville Beach is very popular to visit on hot and sunny days in the summer. Though it certainly isn’t the nicest beach in Maine, it can still be worth the stop if it suits your fancy.

For those looking for something a bit more secluded and local, then nearby Ducktrap Beach is a good option. Even if you don’t want to visit the beach, Lincolnville also boasts a cute downtown area with plenty of shops and a handful of restaurants that can be worth browsing.

Belfast, Maine

The last major town before continuing on to Mount Desert Island is the lovely settlement of Belfast. There are lots of cool things to do in Belfast and it is one of the larger cities in this area of Maine – with a whopping 7,000 people who call it home!

There is a lovely downtown to explore filled with great restaurants, art galleries, artisan shops, and much more. There is also a nice waterfront and harbour to walk along, a few museums to visit, and a number of different farmer’s markets on various days of the week.

From Belfast, it is about another hour and twenty-minute drive before you reach Bar Harbor.

Where to Stay on the Boston to Bar Harbor Drive

If you want to make all or even some of these stops along the way to Acadia National Park, then you’re going to want to stop for a few nights along the way. The best places to do that are in Portland and Camden.

In Portland, you will have time to explore the city and the areas surrounding it. Camden is the ideal location for exploring the midcoast region, nearby Rockland, and more.

West End Inn – This quaint bed and breakfast makes for an excellent place to stay in Portland and a perfect base while on your road tip Bar Harbor. Centrally located in downtown Portland, it’s perfect for exploring the city and its surroundings. There are plenty of great rooms available and a wonderful breakfast offered each morning.

The Press Hotel – If you’re after a bit of luxury during your stay in Portland, then this swanky hotel is an excellent option. Centrally located close to all of the top sites of Maine’s largest city, they have a number of plush rooms on offer, a restaurant on site and plenty of other amenities to ensure you have a great stay.

Private Rental – For those after their own place, there are plenty of private vacation rentals on offer in Portland. This chic apartment in the Arts District is just one example of many great properties available in the city.

Not quite what you’re looking for? Click here to browse more Portland hotels!

Abigail’s Inn – If you’re looking for a charming bed and breakfast in Camden, then this is a perfect place to rest your head when on your road trip. They have countless beautiful rooms on offer, a great breakfast available each morning and the perfect location for exploring the midcoast region.

Blackberry Inn – For those after a bit of luxury, this inn is a great choice for you. Located in the heart of Camden, this place makes for the perfect romantic getaway. All rooms are spacious and feature a seating area and/or a balcony and there is a hearty breakfast included each morning.

Private Rental – For those looking for your own space in Camden, a private vacation rental is a great choice. A place like this charming cottage is just one of many to choose from in the area.

Not quite what you’re looking for? Click here to browse more Camden hotels!

Bar Harbor Grand Hotel – Located in central Bar Harbor, this hotel is the perfect base on Mount Desert Island. Centrally located close to everything this town has to offer, they have a number of great rooms available and a complimentary breakfast to enjoy each morning.

Bar Harbor Inn and Spa – If you want a plush experience while visiting Acadia National Park and Bar Harbor, then this hotel is an excellent choice for you. They have a myriad of luxe rooms on offer, a full-service spa to enjoy and plenty of other fantastic amenities to ensure your stay is a memorable one.

Private Rental – If you’d like to have your own place from which to explore Acadia and Mount Desert Island, then a private holiday rental is a good choice for you. There are lots of places to choose from – like this cottage in downtown Bar Harbor – that can suit many travel styles.

Not quite what you’re looking for? Click here to browse more Bar Harbor hotels!

Planning the perfect road trip from Boston to Acadia National Park is only a struggle when you consider just how much there is to see and do on this drive. Make sure you set aside enough time to enjoy what this beautiful section of New England has to offer!

Are you road-tripping to Acadia? Have any questions about this drive? Let us know in the comments!

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About Maggie Turansky

Maggie is a co-founder and writer for The World Was Here First. Originally from the US, she has lived in five different countries and has travelled to dozens more, both solo and with her partner, Michael. She particularly loves exploring Spain and spending time in the Caucasus and the Baltics. Read more about Maggie

15 Stops on a Boston to Bar Harbor Maine Coast Road Trip Itinerary

Lobsters and lighthouses. Charming towns and rocky coasts. The best way to discover the beauty and uniqueness of Vacationland is with a Boston to Bar Harbor road trip along the Maine Coast. I’ve driven this way many times and each time I discover something new. After so many trips to Maine, I put together this one to two-week Maine coast road trip itinerary from Beantown all the way up to Acadia.

If you are traveling from Boston to Bar Harbor, you will want to take at least a week to explore the Maine coast. Of course, you can drive straight through in under five hours, but there is so much to see on the Maine coast.

This Maine coast road trip includes some of my favorite places to go in Maine in the summer , with stops in:

The Maine beaches region
Maine’s midcoast including Boothbay Harbor, Rockland, and Camden
Acadia National Park

After spending a few days around Bar Harbor, you can then take a fast way back home or continue Downeast off the beaten path to the New Brunswick border.

Where to Stop on Coastal Maine Road Trip

two row boats on a salt pond at sunset with purple and pink reflections in the water in Kennebunkport

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Day 1-2: Maine Beaches

The first region you will encounter on your Maine coast road trip will be the Maine Beaches. Of course, if you have even more time, you can always add in stops in Salem , Gloucester , Newburyport, or Portsmouth on your way up to Maine.

With a one-week itinerary, plan on spending at least two nights exploring this region. You can always break up two to three nights between two destinations to really get a sense of the differences between the various towns.

Fried clams and fries on a blue table from Bob's Clam Shack

Your first stop in Maine is just across the border in Kittery. Kittery is known for its extensive shopping outlets, some of which you may not find in every outlet mall. But I don’t come to Maine to shop, at least not at brand-name outlets.

My first stop is usually at Bob’s Clam Hut , just north of the Kittery outlets on Route 1. While Bob’s is a popular tourist stop, they actually have some of the best lobster rolls and fried clams around. The lines are long for a reason. And yes, the lines are loonnngg. Don’t be surprised to find the parking lot full and the wait for food an hour long in high season.

On my recent trip, I decided to skip Bob’s and try something new so I went where the locals hang out and tried the quieter Chauncey Creek Lobster Pier. You can watch the lobster boats coming in while eating fresh seafood right on Chauncey Creek. But I’ll be honest with you, I still prefer Bob’s.

For a scenic stop, you can also check out Fort McClary, a historic fort in Kittery Point where you can walk along the battlements and get a view of two lighthouses in the distance. There are picnic grounds here for a scenic lunch.

Fort Foster is another great spot for spending a day outdoors, with excellent views of the entrance to Portsmouth Harbor and Whaleback Light, Portsmouth Harbor Light, and Fort Constitution. But you do need to a pay $20 per car parking fee.

Your next stop in the Maine Beaches, about 15 minutes up the coast, should be York Harbor and the York Beaches. Foodies will want to make a pitstop at the Stonewall Kitchen factory store on Route 1 in York. Here you will find all the delicious Stonewall Kitchen sauces, dressings, and other food products, as well as cooking classes and the culinary school, and a cafe.

York Harbor is a quaint oceanfront area with a few rocky beaches that are connected by the York Cliff Walk. If you are looking to stay overnight in this area, the York Harbor Inn is perfectly located right across from the town park and the entrance to the Cliff Walk . The Stage Neck Inn is another great choice.

The York Beaches, both Long Sands and Short Sands Beach are great for surfing, but the accommodations around the beaches are primarily seaside motels. This is also where you will find a majority of the gift shops, restaurants, and souvenir shops. Nearby you have family attractions like York’s Wild Kingdom, mini golf, and more. If you are looking for a quaint downtown and nice sand beaches, head a little further north to Ogunquit.

Cape Neddick

Before you get to Ogunquit, be sure to stop in Cape Neddick, just five minutes further, at the Nubble Lighthouse . Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door (bring cash!) or Dunne’s Ice Cream down the street.

From here, follow Shore Road 15 minutes north into Ogunquit. If you are looking to stay in this area and are ready for a splurge, overnight at the luxurious Cliff House Maine .

boats in the harbor in Perkins Cove in Ogunquit

Ogunquit is very popular with travelers and many of the hotels and motels are not located right on the beach. So if the beach is your priority and you want to stay overnight, be sure to check and see if your accommodations are truly beachfront. The town itself is quaint and upscale, but also touristy. You will find a mix of fine dining options along with your typical tourist clam shacks and seafood restaurants. Ogunquit makes a nice place for a day trip.

We like to stop into Perkins Cove , the small shopping and dining area on the harbor. I’ve eaten at Barnacle Billy’s in Perkins Cove and it was fine, but there are probably better options in the area. In Perkins Cove, you can take in the view of the incoming fishing boats from the Footbridge, or take a 1.25-mile stroll along Marginal Way, past stately inns and rocky beaches.

Kennebunkport

If you haven’t stopped yet, you will want to bed down for your first night in the popular town of Kennebunkport , just another 25 minutes further north. There are many options near downtown Dock Square, but I would recommend a stay at The Inn at English Meadows . This lovely mid-18000’s Greek Revival-style inn is located in Kennebunk’s Lower Village, just a half-mile walk to downtown Dock Square. Perfect for romantic getaways , this bed and breakfast has been tastefully renovated to offer historic charm with modern luxuries such as Frette fine linens, toiletries by Malin+Goetz, and comfortable Vera Wang beds.

There are some accommodations that can fit a family, but families may prefer a resort such as Nonantum Resort , just south of town and on the water, even if not on the beach.

Cape Porpoise fishing pier and lobster boat

In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack. We also like to head out of town to Cape Porpoise Chowder House , which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. I’d highly recommend a scenic drive around Cape Arundel, although it will cause some serious house envy!

If you are looking for beach time, Gooch’s Beach is wide and long and great for families, but street parking is limited so get there early. You can also try nearby Goose Rocks Beach or Colony Beach.

Old Orchard Beach

Thirty minutes north of Kennebunkport is another popular beach town. Families love Old Orchard Beach not only because it has a gorgeous, flat, wide beach, but kids also love the rides at Palace Playland and the arcade games at the pier. This section of the Maine beaches feels almost out of place given the rest of the Maine coast, almost as if someone plucked it off the Jersey shore and plopped it in Maine.

My daughter also loves going to Funtown Splashtown , an amusement park/water park, nearby. But if the boardwalk vibe isn’t your jam, you might want to skip over Old Orchard Beach and try Scarborough Beach State Park instead.

Day 3-4: Portland

Portland Head Lighthouse and surrounding rocks

I would recommend spending one to two nights in the Portland and Casco Bay region, 25 minutes north of Old Orchard Beach. On your way into town, be sure to stop at Portlandhead Light in Cape Elizabeth. It is a great place to scramble on the rocks, walk along the coast, and enjoy those lighthouse views.

We love staying in the Old Port area at the Press Hotel , AC Hotel Portland , Courtyard Marriott, Hilton Garden Inn, or Cambria Old Port. Downtown Portland is a foodie city, with many great restaurants to try. You can also take a tour on the Beer Bus or stop at one of the many breweries nearby. My favorite one to tour and visit is Allagash Brewing Company. For some great lobster with a view, go to Luke’s Lobster on the wharf.

You can hop on a ferry boat and explore some of the islands in Casco Bay, or sign up for a lobster boat tour, where you can learn all about lobstering and help pull up the traps. Best of all, you can eat what you catch! If you don’t want to stay in town, you can also enjoy a car-free couple of nights at the Inn at Diamond Cove on Great Diamond Island.

Freeport (day trip from Portland)

Woman standing in front of giant Bean Boot in front of the L. L. Bean company store in Freeport Maine

From Portland, you can also take a day trip to Freeport, about 20 minutes north of Portland. Famous for being the headquarters of L.L. Bean , it has become a shopping mecca. In addition to the large company store and L.L. Bean outlet, many other designer outlets and outdoor outfitters have set up shop in town.

You can also stop in for a tasting at Maine Beer Company and sample some of their IPAs. If you are looking for a great lobster roll nearby, head down to the water at Harraseeket Lunch and Lobster Company .

Day 5-6: Maine’s Mid Coast

After your time in Portland, it is time to move on to Maine’s midcoast. This area has miles of coastline, hundreds of islands, and countless charming coves to explore. Picture an open hand pointed down with outstretched fingers and you can imagine the many peninsulas that jut out into Casco Bay and the Atlantic Ocean.

It is good to base yourself in this region for at least two to three nights, broken up between two or more destinations. Although many vacationers might decide to spend a week on Orrs Island and be quite content.

Your mid-coast exploration can start off in the town of Brunswick, a 30-minute drive from Portland, with a walk across the Androscoggin Swinging Bridge . This pedestrian bridge connects Topsham and Brunswick, offering beautiful views of the Androscoggin River. After, take a stroll through downtown Brunswick, home to Bowdoin College.

Harriet Beecher Stowe, the author of Uncle Tom’s Cabin and member of the Underground Railroad, lived and worked in town and her house is now a designated National Historic Landmark. If you need a good lobster roll in this area, head to Cameron’s Lobster House.

From Brunswick, head south on Route 123 to the tip of the peninsula for lunch at Erica’s Seafood . This little hidden gem offers seafood fresh off the boat that you can enjoy at picnic tables overlooking the harbor. From there, turn towards Route 24, which leads down through Sebascodegan Island to the town of Harpswell, Orr’s Island, and Bailey’s Island.

You will get to the end of the line when the road reaches the ocean at Land’s End gift shop. Backtrack a little to the Giant’s Stairs Trail . You can park at the All Saints by-the-Sea Episcopal Chapel and walk along the path that runs parallel to the rocks that make up the Giant’s Stairs. When I went, I was hoping for something more like Giant’s Causeway in Northern Ireland. The rock formations aren’t that unique but it is still a cool view and fun place to explore.

If you have more time in the area, you can spend a day at Reid State Park or Popham Beach, or visit the Maine Maritime Museum in Bath. You may also want to line up for a lobster roll at Red’s Eats in Wiscassett, just don’t make my mistake, be sure to get there before they close! Give yourself about an hour to get from Giant’s Stairs to Boothbay Harbor.

Boothbay Harbor

Boothbay Harbor was one of the first places I visited in Maine, over twenty years ago! I was happy to see that it has only gotten better since my last visit, although the good old Tugboat Inn is still there! This time I stayed at the lovely Harborage Inn , which was located right on the water and just a short walk into the center of town.

In town, there are so many cute shops, from Maine Sea Bags to Sherman’s Books, along with other gift shops, galleries, and boutiques. You will also have your choice of restaurants including Mine Oyster, Kaler’s Lobster, Boathouse Bistro, Ports of Italy, and Shannon’s Unshelled.

For lunch, I would recommend eating fresh seafood outside at Boothbay Lobster Wharf . It is across the bay from town but you can easily walk across the pedestrian bridge connecting the two sides of town.

A very popular thing to do in Boothbay Harbor is to take a whale-watching tour. However, since I’ve been whale watching many times, on this trip I opted for a puffin cruise with Cap’n Fish out to a wildlife preserve on Eastern Egg Rock instead. This 2.5-hour cruise passes by lighthouses on the way, with opportunities to see dolphins or even whales.

The boat is large so it can only get so close to the island, however, the puffins often raft up in the water along the shore so you are bound to see plenty of puffins. Just bring along some good binoculars or a super zoom lens because puffins are small and you won’t get to see their cute, colorful beaks without a little assistance.

Read more: things to do in Boothbay Harbor, Maine

Damariscotta

Shucking an oyster at Glidden Point oyster farm

From Boothbay Harbor, it is only 15 minutes over to Glidden Point Oyster Farm on the Damariscotta River. I was hoping to take a oysters and wine-tasting cruise with Damariscotta River Cruises , but unfortunately, they weren’t running on the day I was in town. So an oyster farm tour seemed like the next best thing!

Eighty percent of Maine’s oysters are farmed in the Damariscotta River! My tour at Glidden Point Oyster Farm explained why the river was the perfect spot for oysters and its history that goes back thousands of years to pre-Colonial times. After learning about the farming process, I stepped up to the window to order some oysters to taste on their outdoor patio. I even learned to shuck an oyster! And I was thrilled to learn that Glidden Point ships nationwide.

If you have more time to stay in the area or prefer a quieter town versus Boothbay Harbor, Damariscotta has a very cute but small downtown. Stop into the Sherman’s Maine Coast Book Shop and Sheepscot River Pottery. You can also visit the Whaleback Shell Midden State Historic Site.

You can stay at the Newcastle Inn and have dinner at King Eider’s Pub or Newcastle Publick House. Locals love Shuck Station Raw Bar and if you want to head a little out of town for some beer tasting, stop into Oxbow Brewing Company at their rural farmhouse brewery.

Pemaquid Point Lighthouse

From Damariscotta, it is a 20-minute drive down to the Pemaquid Point Lighthouse , which can be a great spot for sunset. Of course, when I went it clouded up so I didn’t stick around that long, but that’s ok because I was able to get to my next stop in Rockland a little early.

From Bristol, it is an hour’s drive to Rockland. I took Route 32 through Bremen and it worked out perfectly when I came across a park with fields of beautiful purple and pink lupines stretching down to the water. If you have time, also stop at the Marshall Point Lighthouse (you may have seen this in Forest Gump.)

Rockland is the Art Capital of Maine, a bustling town with art museums, galleries, shops, and restaurants on a working waterfront. It is also a port for Maine Windjammer ships and even small-ship cruises, so it attracts its share of day trippers as well.

It is certainly a larger and more touristy town than many of the others along the Maine coast, but I loved it and returned recently to spend some time before my Maine Windjammer Cruise on the Schooner Heritage.

Make time to visit either the Farnsworth Art Museum , which celebrates Maine’s role in American art, or the Contemporary Arts Museum downtown. If it is open, you can also stop into the Project Puffin Visitor Center to learn about all things puffin. It is a fun town to explore, check out the many murals and public art, and shop at the many boutiques (my favorite was Barefoot in Denim !)

There are so many great spots to eat in town. I had an amazing dinner at Primo, a farm-to-table Italian restaurant just a short drive from downtown. I’d also recommend Rock City Coffee and Rock Harbor Brewing.

If you have time, just south of town follow signs for the breakwater. It is about a mile walk out along the breakwater to the lighthouse at the end, but it is a fun outing on a nice day. Another day trip option is to take a ferry to Vinalhaven, which is known for its beautiful scenery, rocky coast, and granite quarries.

The best place to stay in Rockland is 250 Main Hotel . This modern, art-forward hotel has a rooftop deck overlooking the waterfront and spacious rooms.

Read more: things to do in Rockland , Maine

Maine Windjammers at dock in Camden Harbor

A 15-minute drive from Rockland, Camden is another popular town on Maine’s midcoast. There are excellent views of the Camden harbor front from the Camden Public Library, and the lawn is a great spot to enjoy a picnic or relax and soak up the view.

Downtown there are many shops and restaurants, such as The Waterfront Restaurant, Peter Otts, and Fresh and Go. If you would rather stay in Camden instead of Rockland, the Lord Camden Inn is right in the center of everything, while the Camden Maine Stay Inn will be a bit quieter and laid back.

Outside of downtown, you can enjoy scenic views from the top of Mt. Battie in Camden Hills State Park. Also, try hiking along Maiden’s Cliff or the Megunticook Ocean Lookout Trail. Unfortunately, during my visit the fog rolled in and I could barely see to drive through that area, let alone take in a scenic view.

Before you get to Bar Harbor on Mount Desert Island, you may also want to stop at the Penobscot Narrows Bridge & Observatory or visit Fort Knox State Park. That was my plan too but with the fog, it wasn’t worth it.

Day 7-8: Bar Harbor

Camden to Bar Harbor is about an hour and forty-minute drive, although you may want to stop in Ellsworth before arriving on Mount Desert Island, for a beer tasting at Fogtown Brewing Company. Instead of staying in the town of Bar Harbor, I chose to stay at Terramor Outdoor Resort about 15 minutes from Acadia National Park and Bar Harbor.

If glamping isn’t your thing, you may want to opt for the luxurious Claremont Hotel in Southwest Harbor or the charming Salt Cottages overlooking Hulls Cove. Of course if you are going all the way to Bar Harbor, you will want to spend some time downtown and walking along the Shore Path along Frenchman’s Bay. From town you can also take a whale watching cruise. Bar Harbor is also a fun town for shopping and restaurants.

If you are visiting Acadia National Park in the summer, be prepared for crowds and make reservations if you want to drive to the top of Cadillac Mountain for sunrise. (You could try this Acadia National Park sunrise hike instead!) To avoid crowds, also check out these things to do near Acadia .

A Maine coast road trip should be on everyone’s bucket list. It is hard to get tired of seeing fishing boats bobbing in a harbor, lighthouses standing tall over rocky coasts, and eating endless amounts of lobster and seafood. Hopefully, this itinerary makes it easier to plan your trip!

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Best of New England Road Trip

You’re in the driving seat

Go sightseeing in Boston, then hit the road on an unforgettable journey

Driving through New England is spellbindingly beautiful. See wind-beaten coastlines peppered with sailing boats, dotted with lighthouses, and swathed in dunes. Visit cities with history and heritage proudly displayed in architecture, museums, and monuments. And explore rugged wilderness so enchanting it inspired great writers like Emerson and Thoreau.

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Best of New England Road Trip

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Recommended itinerary

Fly to the east coast.

Boston's key sights are an obvious draw for those keen to know the USA’s history better. But you’ll also encounter an impressive foodie scene, friendly culture, and the chance to experience the atmosphere when the Red Sox play a home game.

What to do in Boston

Take a tour.

The best way to get to know Boston is on foot. Following the well-marked Freedom Trail helps understand Boston’s place in history, but a food tour of North End reveals the neighbourhood’s Italian connections. You can find the time to do both on a day-long tour.

Where to stay in Boston

Outstanding hotels.

For a real sense of place, experience an arty take on Boston’s history at The Revolution in the SoWa area. However, if you fancy somewhere more classically elegant, look no further than Fairmont Copley Plaza.

White Mountains

Pick up your car.

From Boston, your road trip begins. You’ll head north on a 150-mile journey into the White Mountains National Forest. While the White Mountains are dusted white in the winter, they're richly green in the spring and summer, and in autumn, they wear a blanket of dazzlingly fiery hues. There's no bad season to experience this heavenly enclave of New Hampshire – each brings its own roster of happenings, whether you're up for an active challenge or simply want the sights to come to you on gentle scenic drives or train rides.

What to do in the White Mountains

Explore outside.

The scenery is beautiful in these parts. You’ll want to drive the Kancamagus Scenic Byway, a nature-hugged highway that weaves through the White Mountain National Forest, where falls, gorges, and mountain peaks will leave you in awe. You could also take the Mount Washington Cog Railway to the summit of the highest peak in the northeastern USA.

Where to stay in the White Mountains

A room at the inn.

Stay in a quintessential New England Inn – something like the Bretton Arms Inn will do nicely – it’s an oversized version with plenty of facilities. Otherwise, North Conway is another lovely small town with shops, bakeries, and plenty of outfitters to help you get outdoors.

Portland, Maine

Coast-bound.

Drive 65 miles southeast to the coastal city of Portland, set on a three-mile peninsula. Portland’s heyday could have been and gone back when its Old Port bustled with activity and ships (guided safely in by its iconic lighthouses) unloaded their cargo into the redbrick warehouses. But happily, it’s a place that’s kept pace with the world, with a burgeoning cultural scene that attracts a curious crowd – impressive for a city of comparatively diminutive proportions.

What to do in Portland

Wander through time.

Spend your days strolling and spotting remnants from Portland’s past, whether the 18th-century architecture in the Old Port or grand old Victorian buildings in the elegant West End. Outdoor activities are always on the agenda here, but the city is equally proud of its excellent food served in world-class restaurants, street food vans, and lobster shacks.

Where to stay in Portland

A room with a view.

Make the most of Portland’s waterfront location and stay somewhere with a beautiful ocean view. Hyatt Place Portland Old Port is in the city’s historic neighbourhood.

A sun-splashed finale

The longest leg of your road trip is the 200-mile journey from the White Mountains to Cape Cod. Cape Cod epitomises the classic American seaside and has a storybook landscape of white-steepled churches and historical towns hemmed by sandy beaches and crisscrossed by smooth biking trails. Perhaps it’s no wonder that urban families make a beeline here come summer, searching out Cape Cod’s Americana charm and outdoorsy lifestyle.

What to do in Cape Cod

Lobsters and lighthouses.

Provincetown’s main artery is chock full of colourful shops, art galleries, flower-filled gardens, and historic buildings. The water will beckon – perhaps you’ll take a ferry to glorious Martha’s Vineyard or nautically-minded Nantucket for a memorable day trip?

Where to stay in Cape Cod

Beach adventures.

Finish your road trip with a beach break on Cape Cod’s sands. If you’re visiting as a family, the Cape Codder Resort has plenty to entertain little ones after days out exploring Cape Cod's towns, beaches, and restaurants.

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Fantastic Boston To Maine Road Trip Itinerary (2024 Guide)

Last Updated: July 18, 2024

Looking for a scenic drive through New England? This Boston to Maine road trip itinerary will help you plan your coastal adventure!

There is no better way to explore New England’s sandy beaches, coastal towns, and lush forests than a road trip!

This Boston to Maine road trip takes you up through Massachusetts, New Hampshire, and Maine as you travel to Bar Harbor and Acadia National Park.

The itinerary includes historic towns, coastal gems, and all the iconic New England sights such as lighthouses, museums, beaches, islands, and more.

Get ready to breathe in that fresh sea air and feel the cool breeze as you embark on a scenic drive from Boston to Maine!

Check out our 3 Days in Boston Itinerary to help you plan your stay in the city.

Table of Contents

How long is a Boston to Maine road trip?

How long is a boston to acadia national park road trip, when is the best time of year for a boston to maine road trip, budget – holiday inn express, mid-range – hilton boston park plaza, luxury – the newbury boston, hampton beach, budget – la quinta by wyndham portland, mid-range – portland regency hotel & spa, luxury – the press hotel, budget – bar harbor villager motel, mid-range – bar harbor manor, luxury – sand bar cottage inn, acadia national park.

The exact duration of a Boston to Maine road trip depends on your destination! Maine is the largest state in the New England area, and there is lots of ground to cover.

So if you’re driving from Boston to Kittery, a town at the very southern tip of Maine, the drive is only 1 hour and covers about 60 miles.

You can make some stops in northern Massachusetts and New Hampshire along the way, but Boston to southern Maine would still only be a few hours at most.

But if you were driving from Boston to Van Buren, a small town at the northern tip of Maine, the drive is almost 7 hours and covers about 430 miles.

So it’s about 6 hours to just drive the length of Maine!

For this Boston to Maine road trip itinerary, the final destination will be Acadia National Park. This is the most popular road trip route from Boston to Maine. Not many tourists head further north than Bar Harbor unless they are road-tripping up to places in Canada such as Nova Scotia or New Brunswick.

Acadia National Park is about halfway up the coast of Maine. To drive directly from Boston to Acadia National Park, it’s 4.5 hours and 275 miles.

For this coastal New England road trip, the duration is about 7 hours and 320 miles including all the recommended stops. The road trip can take even longer if you choose to add more destinations or spend a decent amount of time in each place.

No matter how long you choose to make your road trip, you can fly into Boston Logan International Airport, rent a car, and hit the road! Boston has lots of car rental places all over the city as well if you’re not flying in.

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Summer and autumn are the best times to complete any New England road trip. As you head north from Boston, temperatures get cooler so summer has the best weather for outdoor activities.

New England has lots of beautiful lakes, beaches, hiking trails, islands, and bays. Summer will have the nicest temperatures for swimming, hiking, camping, exploring, and taking boat tours. Summer is also the busiest time of year for a New England road trip, but it’s worth braving a few crowds to have warmth and sunshine.

Autumn is also a stunning time of year to road trip from Boston to Maine. Temperatures will start to cool off, which is great for hiking. Plus, you’ll get to witness some magnificent fall foliage as you drive through the forests!

Winter in New England is freezing and full of snow and ice. Driving conditions are not ideal in winter, unless you’re experienced at driving in the snow and you have a sturdy, 4WD vehicle well-equipped for winter.

New England is still beautiful in winter, and those looking for ski and snowboard destinations may prefer to do their road trip in the snow season. But for a coastal Maine road trip, summer and autumn are definitely the best times to travel.

Boston to Maine Road Trip Itinerary

So let’s dive into the Boston to Maine road trip itinerary! We’ll include all the best places to stop on the way from Boston to Bar Harbor.

Bar Harbor is the gateway to Acadia National Park, so either of these can be your final destination. Of course, you can continue to road trip further north and explore more of Maine and Canada! But northern Maine gets very remote, so for this road trip we’ll just be focusing on Boston to Bar Harbor and Acadia National Park.

Find more epic road trips from Boston to further explore the area!

As the capital city of Massachusetts, Boston is the largest city in New England. It’s also one of the most famous cities in the USA. Thanks to its American history, popular sports teams, unique neighborhoods, and charming waterfront, Boston has much to offer travelers.

Before you embark on your New England road trip, spend a few days enjoying the wonders of Boston!

Stroll through the historic Faneuil Hall Marketplace and grab a fresh lobster roll or search for souvenirs. Follow the Freedom Trail and check out the historic sites that played a vital role in the USA’s fight for independence. Have a picnic in Boston Common, cruise around the city on an educational Boston duck tour , or catch a show in the theater district.

Sports lovers can try to catch a game at one of the iconic sports venues in Boston. Check out a Boston Celtics game or Boston Bruins game at TD Garden or visit the famous Fenway Park for a Red Sox game.

Find more things to do in Boston with our complete guide!

Where To Stay In Boston

Before your road trip from Boston to Bar Harbor and Acadia National Park, spend at least a few days soaking in the history and culture of Boston. Here are some top-rated places to stay.

One of the more affordable hotels near downtown Boston is the Holiday Inn Express . Located in Cambridge, this budget hotel is conveniently located near the New England Aquarium, the Bunker Hill Monument and Boston Common.

A 4-star hotel in the theater district of Boston, the Hilton Boston Park Plaza offers accessible luxury for travelers. It’s right in the heart of the city and has lovely rooms equipped with all the amenities you need for a comfortable stay.

If you’re looking for some real luxury before you drive from Boston to Bar Harbor, check out the Newbury . An exquisite, 5-star property with elegant design and incredible amenities, the Newbury is right in Back Bay and is a fabulous place to spend a few days in the city.

Distance from Boston: 30 minutes
Driving time: 22 miles

From Boston, it’s time to start heading north towards Maine! Before leaving Massachusetts, stop in the northern city of Salem for an interesting historical journey through time.

This coastal city is best known for its legendary Salem Witch Trials of 1692, a period of hysteria that led to the execution of twenty individuals accused of witchcraft.

Today, Salem embraces its eerie past with numerous museums, historic sites, haunted ghost tours, and annual events that attract visitors from around the world. Learn about the craze of witchcraft at the Salem Witch Museum , the Witch Dungeon Museum, or the Witch History Museum.

Art lovers have to check out the Peabody Essex Museum , one of the oldest continuously operating museums in the United States. With roots dating back to 1799, the Peabody Essex Museum has a massive collection of art and cultural artifacts from different centuries and locations around the globe.

Other historic landmarks to check out in Salem include the House of the Seven Gables and the Salem Maritime National Historic Site. These showcase Salem’s maritime history rather than its witchcraft history. But as you can see, Salem is an amazing place to visit for those interested in art, history, and spooky stories!

Distance from Salem: 45 minutes
Driving time: 37 miles

As you continue north into New Hampshire from Salem, it’s worth stopping in Hampton Beach during the summer months!

This popular seaside destination in New Hampshire is known for its wide, sandy shores and vibrant boardwalk. For New Englanders looking for a beach getaway in summer, Hampton Beach is one of the best options.

This bustling beach area attracts visitors with its lively atmosphere, featuring a mix of entertainment, dining, and shopping options. There are arcades, bars, seafood restaurants, souvenir shops, and attractions for people of all ages.

You can also go swimming, surfing, jet-skiing, or try all sorts of water sports. Just remember, the Atlantic Ocean is pretty cold in New England! Even in summer, the ocean is very chilly, but it feels great on a hot summer day.

Hampton Beach is definitely a seasonal town and lots of things are closed outside of summer. So you may want to skip this stop if you’re doing the New England road trip before or after the summer months.

Read next: The Ultimate 3 Days in New York City Itinerary

Distance from Hampton Beach: 26 minutes
Driving time: 23 miles

Now that you’ve crossed the border from New Hampshire into Maine, you can start exploring the best Maine beaches, coastal towns, lighthouses, and attractions.

York is one of the oldest towns in the United States. It was established in 1638 and is rich with colonial history. Check out the well-preserved buildings in downtown York such as the Jefferds Tavern and the iconic Old York Gaol.

Other notable landmarks in York include the prominent Cape Neddick Nubble Lighthouse, which is one of Maine’s most photographed lighthouses.

York Beach is also one of the most famous Maine beaches, so this is a great place for a beach day in summer! York Beach is actually made up of both Long Sands Beach and Short Sands Beach, where you can enjoy sunbathing, swimming, and beachcombing. Short Sands Beach also has a charming boardwalk with shops and eateries.

You can also find some cool arcades, museums, eateries, shops, and historic buildings around York. It’s a lovely place to stop as you road trip through Maine.

Distance from York: 45 minutes
Driving time: 44 miles

The next destination is Portland, Maine one of the best places to visit on any Maine coast road trip. The iconic city is known for its craft breweries, great food, artistic atmosphere, and stunning Casco Bay scenery.

Those who love to eat and drink will have a blast exploring this foodie city! You can sample some of the best Maine craft beer or even join a culinary walking tour . All of Maine has amazing lobster rolls, but Portland is a great place to sample some fresh Maine lobster.

Other than food, downtown Portland is full of cool attractions. The Portland Museum of Art is the largest and oldest art museum in Maine. The Portland Observatory offers panoramic views of the city and coast, and the Old Port District has adorable shops, eateries, and charming cobblestone streets.

A sightseeing trolley tour is a fun and interactive way to sightsee and learn about the history and culture of Portland!

Those hoping to explore nature can venture out to Cape Elizabeth to stroll or bike through the greenery of Fort Williams Park. Here you can also find the Portland Head Light. As Maine’s oldest lighthouse , the Portland Head Light is an iconic landmark in New England.

You can also get great views of the lighthouse and the nearby islands from the water on a sunset kayak tour or a sunset cruise in Casco Bay. Portland is also a great place for a whale watching cruise between the months of May and October.

Check out the best things to do in Portland, Maine for more ideas!

Where To Stay In Portland Maine

There is so much to see and do in Portland, Maine that you may want to spend a few days here. It’s also conveniently located near the middle of a Boston to Bar Harbor road trip, so this is the perfect place to take a break from driving and explore one of Maine’s most famous cities. Here are some places to stay in Portland, Maine!

La Quinta by Wyndham offers affordable accommodation right near the hustle and bustle of Portland, Maine. It has free parking, free wifi, a swimming pool, a fitness center, and more!

Located in the iconic Old Port District of Portland, Maine, the Portland Regency Hotel and Spa is just steps away from the waterfront. In addition to amazing rooms, the 3-star hotel has a fitness centre, steam rooms, hot tubs and a full-service day spa so you can stay relaxed during your trip.

The Press Hotel, Autograph Collection is a 4-star hotel in downtown Portland, Maine. With a refreshingly modern design and a convenient location in the historic district, here you can treat yourself to an upscale hotel room during your Maine adventures.

Distance from Portland: 37 minutes
Driving time: 35 miles

From Portland, Maine, continue your road trip north! Bath is a lovely place to stop in Maine for anyone who is looking for charming towns on the rocky coastline.

Bath, Maine, is a picturesque town with lots of rich maritime heritage. Situated along the Kennebec River, Bath is often referred to as the “City of Ships” due to its long history of shipbuilding, which continues to thrive today at the Bath Iron Works.

Visitors can explore the town’s nautical legacy at the Maine Maritime Museum, which offers fascinating exhibits and boat tours . The Maine Maritime Museum showcases shipbuilding artifacts, maritime art, and historic vessels.

The town’s historic downtown area features beautifully preserved 19th-century architecture, quaint local shops, inviting restaurants, and scenic views.

Read next: 10 Incredible Things to Do in Montreal, Canada

Distance from Bath: 35 minutes

Continue along the coast of Maine into Boothbay, another lovely coastal town known for its bustling Boothbay Harbor.

With colorful lobster buoys, historic buildings, and sweeping views of the ocean, Boothbay Harbor is a small but cozy destination on the wild Maine coast. The area is perfect for outdoor adventures including kayaking, sailing, and whale watching.

Get the best views of the islands and wilderness surrounding Boothbay Harbor on a lighthouses and islands harbor cruise . Or admire the soft pastels of sunset on a relaxing sunset sail . Either way, getting out on the water is a must in Boothbay Harbor!

Fresh seafood makes its way into Boothbay Harbor every day, so indulging in a lobster roll at Boothbay Lobster Wharf is another must-do.

For those who are more interested in history, check out cool local landmarks like the Burnt Island Lighthouse or the Boothbay Harbor Memorial Library. Put a fun twist on your sightseeing by joining a haunted ghost walking tour , where you can hear about pirate stories and visit historic sites like the Admiral’s Quarters Inn, Harbor House Inn, and the Opera House.

Distance from Boothbay: 40 minutes
Driving time: 24 miles

From Boothbay Harbor, continue up the east coast of Maine towards Bristol. This serene town on the Pemaquid Peninsula is known for its natural beauty and laid-back atmosphere.

The town is home to the iconic Pemaquid Point Lighthouse, one of Maine’s most photographed lighthouses, perched dramatically on rugged cliffs overlooking the Atlantic Ocean. Visitors can explore the grounds of Pemaquid Point Lighthouse, climb the tower for panoramic views, and learn about its maritime history at the nearby Fisherman’s Museum .

Pemaquid Beach Park nearby offers sandy shores perfect for swimming and picnicking, while nearby Pemaquid Beach is known for its beautiful sunsets and tidal pools full of marine life.

You can discover more of Bristol’s history at the Colonial Pemaquid State Historic Site , where the remains of a 17th-century English settlement and fort provide a glimpse into Maine’s early colonial history.

The quaint village center of Bristol features historic buildings, charming shops, and local eateries serving fresh seafood. Bristol Harbor is also a picturesque spot for watching lobster boats and enjoying waterfront dining.

An Aerial View Of The Coastline Near Bristol, Maine

Distance from Bristol: 55 minutes

Drive about an hour north of Bristol, and make another stop in Camden, Maine. Sometimes called the “Jewel of the Maine Coast”, Camden is an adorable town nestled between the Camden Hills and the Penobscot Bay.

Camden Harbor is the center of the town. Filled with sailboats and yachts, Camden Harbor is a postcard-perfect location that captures the essence of coastal Maine.

The downtown area is also incredibly charming. Spend some time strolling around the scenic streets and checking out the shops, galleries, and eateries. You can even attend a show at the Camden Opera House or book a boat cruise through the harbor.

Check out the nearby Camden Hills State Park for some fresh air and greenery, which features over 30 miles of hiking trails. Hiking lovers can take on the popular trek to the summit of Mount Battie, which offers epic panoramic views of Camden Bay and surrounding islands.

Read next: 9 Spectacular Must-Do Day Trips From Boston

Distance from Hampton Beach: 1 hour and 45 minutes
Driving time: 76 miles

After about an hour and 45 minutes, you’ve reached Bar Harbor, the Gateway to Acadia National Park. Located on Mount Desert Island, Bar Harbor is surrounded by the sapphire waters and rugged islands of the Maine coast. It’s a truly stunning spot that will impress you before you even head into the national park!

Before exploring the wilderness of Acadia, get in touch with the history and culture of the town. Start at the West Street Historic District, a well-preserved collection of Gilded Age historic architecture that is on the National Register of Historic Places.

LaRochelle Mansion is an iconic landmark on West Street. You can learn about the mansion and the other significant places from a local guide on a historic guided walking tour !

Food lovers can join a culinary walking tour of Bar Harbor, and history lovers can visit the Abbe M useum to learn about the Wabanaki Nations and the Native American heritage of Maine.

Those more interested in exploring nature can walk along the scenic Shore Path that winds along the coast, or you can go kayaking and paddleboarding through Frenchman Bay. There is something for everyone in Bar Harbor!

Where To Stay In Bar Harbor

At the end of your Bar Harbor road trip from Boston, you have a few options for where to stay. As Bar Harbor is the gateway to Acadia National Park, many travelers will just stay in Bar Harbor for a few days and explore the park during the day.

You could also just pass through Bar Harbor and spend a few days camping at one of the registered campgrounds in Acadia National Park. But if you prefer more modern amenities and luxury at the end of your Maine coast road trip, here are some places to stay in Bar Harbor.

Stay right in the heart of Bar Harbor at the Bar Harbor Villager Motel . With free breakfast and a heated outdoor pool, you’ll be amazed at the amenities and cheap prices here!

This elegant and historic manor has landscaped gardens and a guest parlor with a fireplace, providing a cozy and heartwarming atmosphere. Bar Harbor Manor is located within walking distance of all the local attractions as well.

Just 800 metres from the beach, Sand Bar Cottage Inn is a 4-star hotel that feels more like a home. The rustic inn has excellent staff and all the amenities you need for a relaxing stay on your trip to Bar Harbor.

Distance from Bar Harbor: 5 minutes
Driving time: 1 mile

Acadia National Park, located mostly on Mount Desert Island on the Maine coast, is renowned for its stunning natural beauty and diverse landscapes. Established in 1916, it was the first national park east of the Mississippi River.

Acadia National Park is one of the most pristine wilderness areas in Maine and is full of gorgeous forests, granite peaks, and rugged coastal views.

One of the most famous features in Acadia National Park is Cadillac Mountain, the highest point along the North Atlantic seaboard. Here you can hike to the top and be among the first people in the United States to see the sunrise from October to March. It’s a good idea to complete the sunrise hike with a local guide , or you can also do the hike during the daytime as well.

Acadia’s extensive network of trails and carriage roads offers ample opportunities for walking, hiking, biking , and horseback riding. If you’re not a big hiker you can also just drive through Acadia National Park and admire the scenery from the car. Book an audio guide so you can ensure you hit the best spots!

Acadia National Park is also home to a rich array of wildlife. Visitors might encounter white-tailed deer, peregrine falcons, and a variety of marine life along the park’s rocky shores.

The park’s tide pools and coastal waters provide a habitat for numerous species, making it a prime location for wildlife observation and photography.

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25 Best Road Trips From Boston
34 Awesome Road Trips From Boston & Best Itineraries (2024)
Road Trips from Boston
30 Best Road Trips From Boston
Road Trips From Boston
34 Awesome Road Trips From Boston & Best Itineraries (2024)

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COMMENTS

34 Awesome Road Trips From Boston & Best Itineraries (2024)
Click here to see why Kennebunkport is one of the best Christmas towns in New England! 15. Bar Harbor/Acadia National Park. Distance From Boston: 4 hours and 45 minutes. One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston.
14 Best Road Trips From Boston, USA (2024 Guide)
Distance from Boston: Between 60 and 115 miles, depending on where you go. Driving time: Between 1-2 hours. Another one of the most popular road trips from Boston is Cape Cod. This iconic peninsula lined with sand bars, coastal marshes, and quaint towns is a popular holiday and retirement spot for New England locals.
THE 15 BEST Road Trips from Boston
Longer road trips from Boston. 1. Orlando. 🚗 1,400 miles ⏱️ 23 hours, 40 minutes. From the magic of Walt Disney World to the popular rides of Universal Studios, Orlando offers endless fun for families and visitors of all ages. Read more Map. 2. Miami. 🚗 1,580 miles ⏱️ 25 hours.
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Trips from Boston: A short drive away. 1. Plymouth. Plymouth, Massachusetts, shares its name with an old English seaside town, and it's mostly known as the spot where the Mayflower docked and established a colony 400 years ago. There's plenty of old architecture and historical monuments around Plymouth to see, and it also has a bunch of ...
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Marblehead would just be a quick Boston scenic drive. Situated along the North Shore of Massachusetts, this place is filled with small-town charm, dramatic, rocky coastlines, options for beaches, great seafood, and historical homes. It's the perfect place to lay back with the family. Driving time: 40 - 50 minutes.
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Whether you're planning a road trip from Boston this summer or a year from now, remember that small New England towns are filled with intimate B&Bs and historic inns, be sure to book with a credit card that will help you maximize your travel purchases, such as the Chase Sapphire Reserve® (3x) or Chase Sapphire Preferred® Card (5x when booked ...
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Road trip destination: White Mountains, New Hampshire. Road trip length: Approximately 2.5 to 3 hours one way. Road trip distance: About 160 miles one way, depending on the specific destination within the White Mountains and the starting point in Boston. Route taken: I-93 North from Boston to the White Mountains.
Best Weekend Getaways From Boston: A Road Trip Itinerary
From seaside towns to mountainous escapes, these are the best road trip destinations near Boston. By Meaghan Agnew. Updated on June 13, 2022 at 5:10 PM. Portland, ...
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A trip to Newport, RI is one of the best road trips you can take out of Boston! The road trip will take about 90 minutes by car and there are a lot of fun things to do! In fact, according to Pamela, Aquidneck Island is also home to Newport! In the island, you will find a lot of breathtaking sea cliffs around the Cliff Walk.
The Best Road Trips from Boston
Cape Cod. 116 miles / 2 hr. 10 mins. A trip to Cape Cod region from Boston is a must, especially in the summer months. To make the most of this road trip, cruise through the Cape's historic towns, including Sandwich, Orleans and Wellfleet. The last stop on this route is the iconic Provincetown, known for its inclusive culture and LGBTQ+ ...
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Road Trip Destinations around 3 hours from Boston New York City, New York (3 Hours: 12 Minutes) What's better than a road trip to the Big Apple? With 5 boroughs, hundreds of diverse neighborhoods, skyscrapers, and Broadway, you could spend weeks in New York without getting bored. It is the city that never sleeps for a reason.
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1. Philadelphia, Pennsylvania. Starting off, we have a fun trip that balances between distance and places, from Boston to Philadelphia. Along the way, you will be passing through the coastal, eastern side of the states New York, Connecticut, Delaware, New Jersey and Pennsylvania, all within a 400-mile (643-km) trip.
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Between high gas prices, limited vacation days, and chaotic air travel, taking a local road trip is more appealing than ever this summer. These five destinations are all within 300 miles (round-trip) of Boston, Massachusetts, making them ideal for quick getaways. Spend less time at the pump and more time enjoying the road. 1. Kennebunkport, Maine.
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7 Amazing Weekend Trips from Boston. 1. North Conway, NH. This picturesque town has everything you'll need for outdoor adventure. North Conway is in the heart of White Mountain National Forest which prides itself in a myriad of outdoor activities including hiking, biking, skiing, and fishing (among others).
EPIC New England Road Trip Itineraries (2024)
The average daily budget for a New England road trip is between $200-$250 - this includes gas, a rental car, lodging, food, drink, and entry fees. Boston is a must see for a road trip in Photo: Roaming Ralph. On any road trip, New England or otherwise, the largest cost will be gas.
New England Road Trip Itinerary: A Two Week Road Trip from Boston
Here's how to make it happen. Table of Contents. The Perfect New England Road Trip From boston. A Two Week New England Road Trip Itinerary. Boston: Days 1-3. Salem and Cape Ann: Days 3-5. Plymouth, Cape Cod and the Islands: Days 5-11. From Martha's Vineyard to the Berkshires and Around: Days 11-14. How to Make It Happen.
Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary (2024)
Spend 1 night. Day 3: Drive to Portland to explore for a few hours, and then make your way to Camden with a few optional detours for lighthouses and great coastal scenery! End in Camden to spend the night. Day 4: Spend the morning in Camden, and then drive to Bar Harbor. Enjoy downtown Bar Harbor and grab dinner.
The Perfect 7-Day New England Road Trip from Boston 2024
Where to Stay in Newport. 📍America's Cup Inn: A small hotel within easy walking distance of most downtown Newport attractions. Each room is uniquely decorated with antique, colonial furnishings. 📍Hotel Viking: On the list of Historic Hotels of America, this hotel is full of character and charm.. Day 3: Mystic to Washington, Connecticut. On day 3 of this 7-day New England road trip, you ...
The Ultimate Boston to Maine Road Trip
Acadia National Park (especially the view from Cadillac Mountain) Camden Hills State Park in Camden, Maine (great view from Mount Battie) Boston Common, Arnold Arboretum and the tree-lined streets of Beacon Hill in Boston. Kennebunkport and its mansions surrounded by trees.
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From Portland, it's just a 3-hour drive to Bar Harbor and Acadia National Park, which is the highlight of any New England road trip itinerary. Tip: On the way up to Acadia from Portland, be sure to make a stop in Freeport, Maine. This town is home to the L.L. Bean Flagship Store and many other outlet stores.
The Best Boston to Acadia National Park Road Trip for 3 to 7 days
If you take the most direct route on Interstate 95, the journey is 275 miles and a little under 5 hours, barring any traffic. Since you'll likely be driving back from Acadia National Park to Boston at the end of your trip, I recommend taking the scenic coastal route on U.S. Highway 1 at least once.
17 Best Stops on a Boston to Bar Harbor Road Trip
Without stopping, the Boston to Bar Harbor drive time along the I-95N is about five hours total and the distance between Boston and Bar Harbor is about 300 miles (483 kilometres). However, staying completely on the I-95 isn't the ideal route to go if you want to make the most out of this road trip. Instead, getting off the interstate once you ...
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Day 1-2: Maine Beaches. The first region you will encounter on your Maine coast road trip will be the Maine Beaches. Of course, if you have even more time, you can always add in stops in Salem, Gloucester, Newburyport, or Portsmouth on your way up to Maine. With a one-week itinerary, plan on spending at least two nights exploring this region.
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Here are a few example road trip itineraries I would recommend! 3-Day Boston to Acadia National Park Road Trip. Day 1: Boston to Portland. Day 2: Rockland and Camden. Day 3: Acadia National Park. 4-5-Day Boston to Acadia National Park Road Trip. Day 1: Boston to Salem or Portsmouth. Day 2: Portland. Day 3 and 4: Boothbay, Rockland, and Camden
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Go sightseeing in Boston, then hit the road on an unforgettable journey. Driving through New England is spellbindingly beautiful. See wind-beaten coastlines peppered with sailing boats, dotted with lighthouses, and swathed in dunes. ... The longest leg of your road trip is the 200-mile journey from the White Mountains to Cape Cod. Cape Cod ...
Fantastic Boston To Maine Road Trip Itinerary (2024 Guide)
Acadia National Park is about halfway up the coast of Maine. To drive directly from Boston to Acadia National Park, it's 4.5 hours and 275 miles. For this coastal New England road trip, the duration is about 7 hours and 320 miles including all the recommended stops.
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Best Road Trips From Boston

Niagara Falls

New York City

Portland, Maine

Acadia National Park and Bar Harbor

Washington DC

Cape Cod and Provincetown, Massachusetts

Philadelphia

Quebec City

Nova Scotia

Myrtle Beach

Longer road trips from Boston

Los Angeles

16 Fun Road Trips from Boston Only A Short Drive Away

This post is part of our North American Destinations Series – you can also read more great road tripping with kids ideas here

3. Portsmouth

4. Newport

5. Newburyport

6. Lincoln

7. Cambridge

8. Providence

9. Martha’s Vineyard & Nantucket

10. Provincetown

11. New York City

12. Castle Hill

13. Glendale Falls

15. Concord

16. Lexington

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Road Trips from Boston – 42 Best & fun getaway ideas for your Massachusetts scenic drive

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Road Trips from Boston – Scenic drives 2023

Martha’s Vineyard, MA

Provincetown, MA

Lake Winnipesaukee, NH

Kancamagus Highway, NH

Franconia North State Park, NH

Acadia National Park, ME

Road Trips from Boston – Places to go within 3 hours

Plymouth, MA

Gloucester, MA

Rockport, MA

Cape Ann, MA

Providence, RI

Portsmouth Harbor Lighthouse

Ogunquit, ME

Nubble Lighthouse, ME

New Port, RI

Portland, ME

Cape Cod, MA

Ipswich, MA

Newport Vineyards, RI

Burlington, MA

Marblehead, MA

Portsmouth, NH

Brattleboro, VT

Woodstock, VT

North Conway, NH

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Road Trips from Boston – Destinations between 3 to 10 hours

Niagara Falls, NY

Green Mountains, VT

Bennington, VT

Montreal Botanical Garden, QC

Hudson Valley, NY

New York City, NY

Philadelphia, PA

Montreal, QC

Montauk, NY

Toronto, ON

Quebec City, QC

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Camden, Maine

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Stockbridge, Massachusetts

Woodstock, Vermont

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