Road Trips from Boston - 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 BostonThings To Do In Boston This WeekendOutdoor Activities Boston, and Free Museum Days In Boston!

Get the lowest price on the very popular Boston Hop On Hop Off Trolley Tour 

Free Museums in Boston - Hop On Hop Off Trolley Tour

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.

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!

Get all the details and book your Boston Hop On Hop Off Trolley Tour  TODAY!!!

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 | 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 trip from Boston | 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. 

Driving time: 2 hours and 8 minutes

Acadia National Park, ME

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

Salem, MA

Salem, MA

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

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

Lowell, MA

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

Road trip from Boston | 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

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.

Driving time: 1 hour and 15 minutes

New Port, RI

Road trip from Boston | 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

Mystic, CT

Road trip from Boston | Mystic, CT

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.

Driving time: 1 hour 30 minutes

Portland, ME

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. 

Driving time: 2 hours

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

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. 

Driving time: 30 – 40 minutes

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.

Driving time: 40 – 50 minutes

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. 

Driving time: 1 hour

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.

Driving time: 2 hours

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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Road Trips from Boston – Destinations between 3 to 10 hours

Manchester, VT

Road Trips from Boston | 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

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.

Driving time: 7 hours 

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

Stowe, VT

Road trip from Boston | Stowe, VT

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

Road trip from Boston | 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

Road trip from Boston | 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

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