Boston is the bustling capital of Massachusetts… a cultural, gastronomic and academic epicenter…and the unofficial capital of New England. The nearby towns of Gloucester, New Bedford, Plymouth, Rockport and Salem are some of the best day trips from Boston to give you a sense of the history, culture, and beauty that New England holds…


A pleasant 45-minute drive from Boston will bring you to Gloucester, an old English settlement founded in 1623, which makes it older than Boston by just 7 years. Gloucester’s longstanding tradition in fishing and shipbuilding began in the early 1700’s. Stop in for delicious craft beer and super fresh seafood at the Cape Ann Brewing Co. (27 Commercial Street).

Harbor views in Gloucester, Mass

Harbor views along the promenade

Cape Ann Brewing Co.'s backyad

View of Cape Anne

Cape Ann Brewing Co.

Beer sampler at Cape Ann Brewing Co.

New Bedford

New Bedford sits 50 miles south of Boston and is often referred to as the whaling city because for years it was America’s most profitable fishing port and main source for whale oil supply. Whaling shaped New Bedford’s history, and in the early 19th century immigrants from the Cape Verde Islands began arriving in New Bedford by the dozens. By the 20th century, Cape Verdeans were coming by the hundreds to work as crewmen on Massachusetts’s whaling ships. Once you are done exploring, take a load off and enjoy some of New England’s famous seafood at New Bedford’s only harbor-front restaurant, Waterfront Grille (36 Homers Wharf).

New Bedford, the "whaling city"

Downtown New Bedford

Boat repairs in New Bedford

Boat yard repairs


Approximately 40 miles from Boston along Massachusetts’s South Shore sits historic Plymouth. Considered “America’s Home Town,” Plymouth is where the Pilgrims landed on the Mayflower in 1620, and where the first Thanksgiving feast took place between the Wampanoag Indians and the Pilgrims in 1621. This is one of the best day trips from Boston and one of the most popular.

This quaint seaside town has a big history. Not many people know that Marilyn Monroe, Presidents George Bush and son George W. Bush, Governer Sarah Palin, Alec Baldwin, Richard Gere, Clint Eastwood, and over ten million other famous (and non-famous) Americans are the direct descendents passengers who landed in Plymouth on the Mayflower.

Plymouth Rock

Sign for Plymouth Rock


Plymouth Rock inscribed with the date 1620

Mayflower II

The Mayflower II – Reproduction of the original ship


Whether you are driving or taking the “T” from North Station in Boston, you will fall in love with Rockport. Not only is it the place where I proposed to my fiancé, it is an ideal daytrip to get out of the city and into a more peaceful state of mind. Rockport takes you back in time to a different place when life was simpler. Rockport, like its neighbor Gloucester, is a town based around fishing and boating in Cape Ann. Fishing boat charters, whale-watching tours, and kayaking are all popular activities during the warmer months.

 Historical Bear Skin Neck

Main street in Rockport

Main Street features cafes, restaurants and shops

Bear Skin Neck view

View of Bear Skin Neck


When one thinks of Salem, I’ll bet the first thing to come to mind is witches! But Salem is much more than a dark blip in American history. It is a historic place that is home to many of America’s treasures. Start off your day at the Salem Witch Museum (19 ½ Washington Square North) The museum was founded in 1972 and has since showcased the complete history and origins of witch hunts in the world and of course, the events of the infamous Salem witch trials. Finz Seafood and Grill (76 Wharf Street) is an ideal place to stop for a tasty lunch along Salem’s Pickering Wharf. Complete your day in Salem by visiting the Peabody Essex Museum.

Salem Wharf, Massachusetts

Ship restoration in Salem Wharf

Salem Witch House

One of Salem’s iconic tourist attractions: The Salem Witch Museum

Witch in Salem, Massachusetts

Witches are everywhere in Salem, even on the streets!

We hope you enjoyed our list of best day trips from Boston. If you have been or are planning a trip there, leave us a question or comment below!