15 Best Boston Road Trips: Weekend Getaways & Day Trips

Located in the northeast of the United States, Boston is the most populous city in Massachusetts and boasts an abundance of attractions and activities to do throughout the year, from watching the Red Sox play at Fenway Park to cheering on the runners in the Boston Marathon and even enjoying a peaceful stroll through the Museum of Fine Art on a winter’s day in the capital city. 

However, if you’re Bostonian born and bred, then you’ve probably exhausted everything there is to do in Boston and are looking for some new road trips to embark on and in need of some inspiration for getaways for the weekend or just for the day.

We’ve compiled a list of the 15 best Boston road trips to add to the travel list so you can explore more of the neighboring areas in New England. 

Salem, Massachusetts

Just a short 45-minute drive from Boston is the coastal city of Salem, known for being the site of the witch trials back in 1692. 

If you’re into all things spooky, then you’ll find the best time of year to visit Salem is around Halloween where there’ll be many attractions for locals and tourists to enjoy, from ghost tours to interactive haunted hayrides. 

Salem is also the home to author Nathaniel Hawthorne who wrote The House of The Seven Gables and you can also visit the colonial mansion that was made famous by the author’s 1850s novel. 

Aside from the witches, you’ll find a peaceful coastline as well as a beautiful art collection in the Peabody Essex Museum. Salem was once a bigger port than Boston and many sea merchants would bring in trade and fine art pieces from the Far East, many of which are displayed in some of Salem’s finest homes that are open for public viewing.

If you’re looking for an exquisite place to stay the night in Salem, then The Merchant Boutique Hotel is highly recommended, and dine out at one of Salem’s many taverns for an evening of fresh oysters and fish at Turner’s Seafood. 

Portland, Maine

A 2-hour drive north of Boston is Maine’s largest city and also another proud maritime destination. Despite being renowned for its rich fishing history, and 19th-century architecture, the city is now a hub of boutique bars and traditional brewery houses that make up an eclectic nightlife experience. 

Maine as a state has over 30,000 miles of rivers and lakes, many of which are in the Portland area, so if you’re into watersports then take a visit to some of the popular spots along the Casco Bay.

Make sure to take time exploring the cobbled streets and pop into some of the nearby independent restaurants and bars that make up the city’s cultural hub.

If you’re ever in town from May through to October, hit up the Portland Farmers Market to pick up some of the best food around that’s in season and brush shoulders with some of the city’s best chefs who are also picking up their ingredients. 

Concord, Massachusetts

Trace back America’s roots by taking a visit to Concord, a town northwest of Boston that’s known for being home to many of the sites of the American Revolutionary War. You can walk the 5-mile trail at the Minute Man Historical Park to walk the steps American militants took before meeting British Troops back in 1775.

The town is also rich in literary culture, accommodating the longtime dwelling of Louisa May Alcott and her family where she also wrote and set her famous book Little Women.

Away from culture and history, Concord also offers some serene nature walks that go on for miles passing through expansive lakes and vast forestry to escape the bubble of the town. 

New York City, New York

Up there with being one of the U.S’ best cities, is NYC, a city so diverse and packed with adventure that it warrants a whole weekend to enjoy what it has to offer when visiting from Boston. 

Luckily enough, Boston offers various transportation options to NYC including flights, driving by car, train, and even the Greyhound bus for as little as $27 for one way.

You can choose to stick to visiting some of the cities’ most popular landmarks such as the Empire State Building, Statue of Liberty, and Central Park, or dedicate yourself to a more laid-back approach by exploring the boroughs of the city on foot. 

Providence, Rhode Island

Just an hour and a half drive away from Boston is Providence, the capital city of the United States’ smallest state Rhode Island, or known to locals as Lil Rhodey. 

Home of Brown University and John & Wales University’s culinary arts program, the city has tons to offer from exquisite cuisine to museums filled with the city’s rich history in industry and manufacturing. 

Take a stroll down to Waterplace Park or take the family to visit the giraffes at the Roger Williams Park Zoo. The city is filled with culture, fun, and education to entertain the whole family. 

Cape Cod, Massachusetts

Cape Cod is a popular vacation spot for Boston residents and also attracts many tourists and internationals who are visiting the New England area. 

Stay in one of the peninsula’s quaint villages and dine out at the independent seafood shacks to get a real feel for the southeastern corner of Massachusetts. If you return from your trip to Cape Cod without having tried a lobster roll, then you haven’t done it right. 

Cape Cod has masses of activities and attractions to fill your weekend getaway from the Cape Codder Water Park with water slides and splash pools to the JFK Museum on Main Street in Hyannis. 

Rockport, Massachusetts

If you’re looking for a more chilled out seaside getaway, then visit the town of Rockport in Essex County, known for its artist population and lobster fishermen who provide a huge chunk of the local cuisine available. 

Regardless of if you’re staying for an entire weekend or just a few hours, Rockport is guaranteed to charm you with its typical American seaside culture and friendly atmosphere.

To avoid the large crowds, plan your visit for the spring or fall months as the town experiences its peak season during the summer. 

Newport, Rhode Island

Newport is known for its lavish mansions that were once the summer homes or known as cottages to the wealthiest families of New York and Philadelphia back in the 20th century.

Nowadays these homes of the gilded age are open to the public and are highly worth visiting if you’re in the area for the day or the weekend.

Many of the scenes from the Great Gatsby were filmed in one of the most popular manor houses in Newport, Rosecliff, which is an imitation of the Petit Trianon in Versailles. 

Aside from luxurious mega homes, the city offers stunning coastal views and a yacht-filled harbor that you can enjoy whilst wandering around.

Nashoba Valley Vineyards

When people mention Nashoba Valley, most people will immediately think of the hills and the ski area that draws in locals and tourists every time the snow comes back around, however, one of Nashoba Valley’s hidden gems is the winery and brewery. 

The vineyard provides a great day out for the whole family, with children getting to enjoy apple picking in the orchard to the adults getting to experience a tour of the vineyard along with a tasting session. Then end a fantastic day by dining at one of the two restaurants – Vinter’s Knoll or J’s to enjoy locally sourced and prepared food. 

White Mountains, New Hampshire

If you’re looking for a place to escape the hustle and bustle of everyday life and want to explore towering peaks and stunning mountain ranges, then make a road trip to the White Mountains in New Hampshire.

The area is great to visit all year round with skiing being popular in the winter and many photographers being attracted during the fall months to capture the warm hues of the ranges. 

The area attracts hikers from around the world, but be sure to plan your trip if you are planning to explore the scenic landscape. 

Newburyport, Massachusetts

An ideal day trip for last-minute plans on the weekend is Newburyport, a seaside town just a 1-hour drive from Boston that many New Englanders forget about. 

Newburyport has managed to retain its old New England charm with architecture ranging back from the 17th century through to the 20th century as you wander through the Newburyport Historic District.

Take a short trip to Plum Island, located just 2 miles from Newburyport to discover some of the best spots for bird watching and make the most of the soft sandy beaches that stretch for 11 miles.

Settle down after a busy day of venturing the area by grabbing a beer at RiverWalk Brewery on Parker Street and then tucking into some Mexican cuisine at Metzy’s just a 10-minute walk away. 

Glendale Falls, Middlefield

Glendale Falls is one of the longest waterfall runs in Massachusetts and has a drop of over 160 feet. The falls themselves may be too far away to warrant a day visit from Boston, but if you’re staying in the Middlefield area or passing through on the way to somewhere else, then it’s worth a stop off. 

There is a well-maintained trail from the parking lot to the bottom part of the falls, where you’ll find a great swimming spot that’s best enjoyed during the hot summer months. 

Hiking and swimming in the area can be dangerous during winter months or after heavy rainfall so take when visiting the area and don’t let your dog off the leash as currents can be especially strong. 

Naismith Memorial Hall Of Fame

If you’ve got some basketball fanatics in your family, then you’ll find the trip to the Naismith Memorial Hall of Fame a trip well worth your while, despite being nearly 2 hours away from Boston. 

There are a handful of dining options on-site for you to enjoy when you arrive at your destination before you begin the tours and some restaurants even offer pre-ordered box lunches for you to pick up. 

Youth pre-sale tickets go for $16.50 whilst adults are $25.50, however, the option to turn up on the day and buy your tickets is available, but a reservation is recommended especially during spring or summer break. 

Kennebunkport, Maine

Another popular vacation spot on the East Coast is Kennebunkport, which also accommodates former president George Bush and his family during the summer months. 

It’s one of the wealthiest communities in Maine and draws in many affluent families during peak season due to the stunning beaches and boating opportunities.

The Dock Square area will be your central hub during your visit, made up of souvenir shops, a multitude of dining options, and interesting art galleries for you to wander around. 

Martha’s Vineyard, Massachusetts

Martha’s Vineyard, an island just off Cape Cod is a quaint yet enchanting summer vacation destination that attracts thousands if not millions to its beautiful shores every year. 

If you’re vacationing in Cape Cod then it’s worth getting the boat across to spend the day on Martha’s Vineyard and then explore the island via a moped rental. Make the most of your time on Martha’s Vineyard by spending a few hours on the beach then head over to the museum before enjoying a tasty lobster roll before getting the ferry back to the mainland. 

Steven Speilberg filmed his 1975 Thriller Jaws on Martha’s Vineyard and there have been spotting some Great Whites located off the coast so stick to shallow waters and listen out for shark alerts.