While Boston has plenty of unique spots to visit and see, consider setting aside some time aside for a day trip from the city. Boston, one of the top vacation spots in the U.S. is the ideal hub for exploring the “Birthplace of America.” Tour quaint coastal communities, discover the secrets of historic sites and eat your way through the region with New England cuisine.
The New England region has pockets full of small historical towns to check out, and AAA can assist you in selecting from some of the best day trips from Boston.
Check out 29 of the best day trips from Boston and explore some of the oldest areas of the United States.
1. Salem, Massachusetts
Just a little under an hour away from Boston is Salem, Massachusetts — the second oldest settlement in New England. Salem is well known for its historical sites and spooky history, including the witch trials of 1692. Those interested in its rich history can join a guided walking tour of Salem or venture solo to Salem Witch Village, Salem Witch Museum and the Witch House.
Not interested in witches? Salem’s downtown area has plenty of shops and eateries to check out. If you’re a history buff, you can see where Nathaniel Hawthorne, who wrote “The Scarlet Letter,” was born — The House of the Seven Gables. Given it's proximity to the city, Salem is an excellent choice for a day trip from Boston by car.
2. Marblehead, Massachusetts
Marblehead, Massachusetts is 17 miles north of Boston and requires about an hour on a train to arrive in the sweet coastal town. First settled in 1629, Marblehead started and continues to be a great fishing community, making it a popular spot to visit for fishermen.
Marblehead has a quaint Front Street downtown full of local shops and eateries. To make the most of your Boston trip, you can do a half-day tour to Salem and Marblehead from Boston with an easy pickup at your place of stay.
3. Gloucester, Massachusetts
Gloucester, Massachusetts is worth a 45-minute drive from Boston. As America’s oldest seaport and one of the earliest settlements, Gloucester has plenty of rich history to enjoy. Check out the Cape Ann Museum for marine art and history. Walk over to Good Harbor Beach to walk along the sandy beaches and view Thacher Island lighthouse.
Whale watching is a popular activity in Gloucester — arrange a whale-watching tour to see nature’s most wondrous marine mammals. Don’t leave without grabbing fresh seafood from a local fishmonger or grabbing a meal at a popular spot like Tonno.
4. Rockport, Massachusetts
Just an hour away from Boston is Rockport, Massachusetts — an idyllic seaside escape from the bustle of the city. Check out Rockport Harbor to see Motif Number 1, an old 1800s fishing shack that was converted into an art studio in the 1900s and now stands as a landmark in the town.
Art enthusiasts will love to peruse through Rockport's 30+ art galleries that include local art. Explore the harbor by renting some kayaks, going on a sailboat excursion or staying on land and going beachcombing. End your day with a few lobster rolls at Roy Moore Lobster Company.
5. Provincetown, Massachusetts
Just a ferry ride away is Provincetown, Massachusetts, a great choice for a day trip from Boston. Sitting on the tip of Cape Cod, Provincetown is well known as a welcoming LGBTQ+ hub — making it a friendly destination for all who visit. It also has unique eateries, such as Lobster Pot and Strangers & Saints, charming local businesses and art galleries.
Provincetown is beautiful to visit in the summertime, as you can enjoy the white sandy Race Point Beach. For history buffs, don’t forget to check out the Pilgrim Monument and Provincetown Museum.
6. Hyannis, Massachusetts
Hyannis, Massachusetts can be referred to as a “small city” compared to other smaller villages on this list. It’s a bit larger in size and conveniences, as it has its own airport and ferry port.
Despite the size, Hyannis’s Main Street and downtown are walkable. You can also take the Hyannis Area Trolley to get to Main Street and other areas of the town. Be sure to check out Kalmus Beach Park, Hyannis Harbor and Cape Cod Maritime Museum for some maritime history and leisure.
7. Cape Cod National Seashore
For the perfect beach day, head to the Cape Cod National Seashore. Stretching over 40 miles, the seashore is home to sandy beaches, coastal bluffs, sand dunes and woodsy marshes. The area also has plenty of opportunities for hiking, wildlife viewing, sunbathing and birdwatching. Spend the day soaking in the sun and enjoying the salty breeze of the Atlantic Ocean.
8. Plymouth, Massachusetts
Plymouth, Massachusetts is widely known as the first settlement of New England by Mayflower pilgrims in 1620. Now, Plymouth is a blend of historical sites and modern attractions. For history enthusiasts, go to the Plimoth & Patuxet Museum, Plymouth Rock and Mayflower II — a life-size replica of the original ship.
After learning more about the village, enjoy the Plymouth waterfront and dine on some local seafood. Finish the day at a local brewery or winery, like Mayflower Brewery.
9. Providence, Rhode Island
Providence, Rhode Island — located on the northern tip of Cape Cod — is another top spot to check out during your trip to New England. Providence is home to the Rhode Island School of Design, so check out the RISD Museum while you’re there. Cruise through the town on a sightseeing tour or narrated boat ride.
If you visit during the summer months, you may see WaterFire, an annual festival that showcases local fire installations over the open water. The town is also well known for its unique eateries, so be sure to join a food tour to taste the best bites Providence has to offer.
10. Newport, Rhode Island
If you’re looking for a day trip to stroll and get your steps in, we recommend visiting Newport, Rhode Island. Admire the beautiful Gilded Age mansions, including The Breakers and Bellevue Avenue. Enjoy the scenic views of the Atlantic Ocean at the Cliff Walk and Easton’s Beach. Finish the day by walking through the Audrain Auto Museum and International Tennis Hall of Fame.
11. Walden Pond
While at Concord, stop by Walden Pond. The Walden Pond State Reservation is mostly known as a literary destination due to its ties to Henry David Thoreau, an American writer and philosopher most known for his book “Walden.” Hike along the mile-long Pond Path and cool off with a swim in Walden Pond.
12. Concord, Massachusetts
Concord and Lexington are both known for their historical significance in U.S. history. Walk the Battle Road Trail and visit the Minute Man National Historical Park. For literary lovers, stop by Louisa May Alcott's Orchard House — the writer of “Little Women.” Afterward, grab a meal at a local eatery, like The Cheese Shop or Woods Hill Table. If you prefer to have a pre-planned trip, we recommend joining one of the Concord Guides Walking Tours.
13. Lexington, Massachusetts
Lexington, Massachusetts is also mostly known for its history, especially around the American Revolutionary War — which started in the very town in 1775. Explore the Minute Man Statue, Hancock-Clarke House and Lexington Battle Green to learn more about the historic events. If you have time, explore the Buckman Tavern and Munroe Tavern — we recommend joining a guided tour to provide more information and context to these locations.
14. The Berkshires
The Berkshires is a rural area in the western mountains of Massachusetts and is known for its outdoor attractions and activities. Enjoy a live concert at the Tanglewood Music Center, visit the Norman Rockwell Museum or hike on the area’s most popular trails, such as the famous Appalachian Trail.
15. Manchester-by-the-Sea
Manchester-by-the-Sea, located on Massachusetts North Shore, is a quaint coastal town known for its lovely beaches and waterfront views. Some of its most popular beaches include Singing Beach and White Beach.
If you prefer being in the water, arrange a private sailing trip along Cape Ann. Manchester-by-the-Sea also has a few great museums, including the Manchester Historical Museum and Hammond Castle Museum —a medieval-style castle built in 1926.
16. Worcester, Massachusetts
As the second largest city in New England, Worcester, Massachusetts has many activities and attractions to explore. Visit the Worcester Historical Museum and Worcester Art Museum for history and art lovers. Go on a nature walk in one of the oldest U.S. public parks — Elm Park — or Green Hill Park. Finish the day by watching Worcester’s minor league baseball team, the Woo Sox, at Polar Park stadium.
17. Lowell, Massachusetts
Lowell, Massachusetts is most known as the birthplace of famous American novelist Jack Kerouac and its rich industrial history. It also has various attractions and museums to check out, including Lowell National Historical Park, the New England Quilt Museum and the Whistler House Museum of Art. You can also spend your day hiking in the Lowell-Dracut-Tyngsboro State Forest or along the Merrimack River.
18. Newburyport, Massachusetts
A little under an hour’s drive away from Boston is Newburyport, Massachusetts. Located on the Merrimack River, Newburyport’s cobblestone streets and Federal-style brick buildings are too gorgeous to miss. Go on a walking tour of High Street to view the homes in the historic district, along with art galleries and boutiques.
Head out to Moseley Woods and Maudslay State Park to enjoy beautiful views of the riverside. For birdwatching, check out Parker River National Wildlife Refuge on Plum Island which protects more than 800 species of animals, plants and birds.
19. Framingham, Massachusetts
Framingham, Massachusetts is just a half-hour drive west outside of Boston. This suburban area is an ideal day trip for nature enthusiasts, with plenty of parks and outdoor activities to enjoy. Spend the day walking or biking at the Framingham Centre Common or Callahan State Park.
Take in the history at the Danforth Art Museum and Framingham History Center. Be sure to visit the Framingham Farmers’ Market if you’re visiting between June and October and pick up some fresh produce and pastries.
20. New London, Connecticut
The birthplace of the U.S. whaling industry, New London has grown into a culturally diverse town with plenty of attractions. Tour the campus of the U.S. Coast Guard Academy and visit the Custom House Maritime Museum to provide insights into New London’s seafaring history. Afterward, visit Whale Oil Row to view the 19th century beautiful Greek Revival houses.
21. Martha’s Vineyard
Martha’s Vineyard is a quaint island off the Massachusetts coast and a popular luxury destination for upper-class families and celebrities. However, it’s still a great place to take a day trip due to its gorgeous beaches, beautiful wineries and unique shops and eateries.
To make your trip easier, arrange a guided day trip from Boston with a Round-Trip Ferry and Island Tour. This route provides a personalized experience of the island while sightseeing the most important sites.
22. New York City
New York City, also known as the Big Apple, is a four-hour train ride south of Boston. There’s a long list of things you can do in the city — we recommend checking out a New York Travel Guide for more inspiration. However, some popular spots to hit during a day trip include Times Square, Central Park and the Empire State Building. If you have time, we recommend grabbing a ferry to do a Statue of Liberty and Ellis Island Tour.
Other NYC historical activities include the National 9/11 Memorial & Ground Zero Tour, the Museum of Natural History and the Metropolitan Museum of Art (The Met).
23. Mystic, Connecticut
Once a shipbuilding center, Mystic, Connecticut is rich in maritime history. For a day trip itinerary, add the Mystic Seaport Museum to explore the Mystic River and more of the town’s seafaring history. Time your trip in July to join in on the festivities of the Sea Music Festival and listen to sailing tunes from around the world.
For movie buffs, head to Main Street to see where the 1988 film “Mystic Pizza” was set and filmed. For Spielberg fans, the 1997 film “Amistad” includes scenes filmed at Mystic Seaport.
24. Castle Island
There’s no need to go far outside the city to explore this unique historical landmark. Castle Island, located on the southern shore of Boston Harbor, is accessible by walking or driving.
The famous park is home to Fort Independence, which used to be a sea defense for the city of Boston. You can take a guided tour of Fort Independence to learn more about its history dating back to 1634. Time your visit to Castle Island on July 4th to see the USS Constitution complete an annual turn-around cruise with a 21-gun salute in front of the fort.
25. Nantucket, Massachusetts
Nantucket Island can be considered one of the most popular places to visit in New England, and there are good reasons why. Located off Cape Cod, this summer destination is well known for its timeless cobblestone streets, historic-style homes and luxury boutiques.
Breathe in the fresh air with a bike ride along the Coskata-Coatue Wildlife Refuge or Milestone, or arrange a private beach fishing trip with a guide. You can get to Nantucket via ferry from Hyannis, Harwich Port or New Bedford, or make a quick flight from Boston Logan Airport.
26. New Bedford, Massachusetts
About an hour’s drive outside of Boston is New Bedford, Massachusetts, best known as an international whaling port in the 19th century. Now, you can explore to learn more about the town’s seafaring history and present fishing community at the New Bedford Whaling Museum.
Afterward, indulge at the local restaurants to try the famous New Bedford scallops and enjoy a leisurely stroll along the harbor’s waterfront or Fort Taber Park.
27. Ogunquit, Maine
Located in southern Maine, Ogunquit is perfect for those looking for a day trip in a walkable town and a short drive (about an hour and a half). This idyllic coastal town sits next to a long slice of beach and is home to waterfront restaurants and shops. It also has a few museums, including the Ogunquit Heritage Museum and the Ogunquit Museum of American Art.
28. Watch Hill, Rhode Island
Watch Hill is a small community in the town of Westerly and is most known for its luxurious homes, stunning beaches and the historic Watch Hill Lighthouse. It’s a popular spot for sailing, surfing and hiking the coastline. Don’t forget to ride the oldest merry-go-round in the US, the Watch Hill Flying Horses Merry-Go-Round!
29. Kittery, Maine
Our last, but not least stop on our list is Kittery, Maine. Kittery is a charming coastal town that refers to itself as the “oldest incorporated town in Maine.” During your visit to Kittery, be sure to check out some of its historical sites, including the Portsmouth Naval Yard.
Need to do some shopping? Head over to Kittery Premium Outlets to purchase items from big-name brands, such as Columbia and Ann Taylor. You can also do a round-up tour to visit Kittery, Salem and Kennebunkport in an all-day private tour to see the best parts of each small town.
Plan Your Trip to Boston With AAA
Boston is a great starting point for countless day trips — and the majority of these don’t require a car, thanks to public transportation, like Amtrak trains. From exploring some of the oldest historical towns in the US to enjoying the peacefulness of small East Coast towns, there are so many day trips from Boston to venture on.
Consider adding a few day trips to your trip to Beantown to explore more of the unique New England region of the country. Use your AAA Membership to save on hotels, attractions and tours, and let AAA Travel handle planning your day trip itineraries.