5 Day Trips from Boston

I strongly recommend renting a car to leave Boston and explore these amazing day trips from Boston. Rockport is where I got engaged and so it will always hold a place in my heart, but Gloucester, New Bedford, Plymouth, and Salem are all worthwhile places to experience. 



A pleasant 45-minute drive from Boston will bring you to Gloucester- an old English settlement founded in 1623, making it older than Boston by 7 years. Gloucester’s longstanding tradition in fishing and shipbuilding began in the early 1700’s. The Gloucester Fishermen’s Memorial on Stacy Boulevard faces the outer harbor and is dedicated to the hundreds of local fishermen who lost their lives at sea. By walking or driving west of the statue on Stacy Boulevard, visitors can visit the Fisherman’s Wife Statue on their way to the Stage Fort Park Welcoming Center.


Beaches, shops, restaurants, and whale watching tours are located east of the Fishermen’s Memorial on and around Rogers Street in Gloucester’s historic district. Stroll the charming brick sidewalks and pick up a Gloucester memento, plan your whale-watching or lighthouse harbor tour with 7 Seas Whale Watch (63 Rogers Street) or stop in for delicious craft beer and super fresh seafood at the Cape Ann Brewing Co. (27 Commercial Street).


Gloucester provides its guests with an array of things to do for the day, whether it is fishing, diving, kayaking, whale watching, or just relaxing by the gorgeous harbor. Whale season typically lasts from late April to late October, and booking in advance is advised, especially during the summer months. If you decide to turn your day trip into an overnighter, make sure to stay at a chique boutique hotel.


Northeast of Cape Ann Brewing Co. is the Cape Ann Museum (27 Pleasant Street), which is home to an impressive collection of maritime artwork. It is a reflection of the pride felt by America’s oldest fishing port. Gloucester is a day trip that the entire family will love. A truly perfect mix of adventure and relaxation.


Driving from Boston: Follow either Interstate 93 or Route 1 to I-95 North (I-95 North and Route 128 are the same.) Follow I-95 North/Route 128 toward New Hampshire and Maine and keep left until exit #45.

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.

See also
The Best Chinese Dim Sum in Boston’s Chinatown + Egg Tart | Boston, Massachusetts


By the 20th century, Cape Verdeans were coming by the hundreds to work as crewmen on Massachusetts’s whaling ships. Keeping with the city’s theme, visitors can check out the New Bedford Whaling Museum (18 Johnny Cake Hill), a 107-year-old institution that holds an extensive collection of whaling artifacts, literature, artwork, ship models, harpoons, and whale skeletons. Marvel at the 37-foot long skeleton of a male humpback whale and learn about its species’ life cycle at sea, or just enjoy the numerous sea portraits hanging throughout the place.


Once you are done with the museum, take a load off and enjoy some of New England’s famous seafood at one of the seaside restaurants along Rodney French Blvd. Then, relive your high school American literature days and visit The Seaman’s Bethel- the whaleman’s chapel mentioned in Melville’s Moby-Dick. Nowadays it is a non-denominational chapel and memorial for whalemen who have lost their lives at sea (15 Johnny Cake Hill). New Bedford’s cobblestone streets give it an old world feel and will transport you to times from long ago when fishermen ruled the land and the sea.


Driving from Boston: Follow I-93 South to I-90 West/Quincy/Worcester, and keep left. Take the I-93 South until exit 4. Merge onto MA-24 South toward Brockton. Take exit #12 to merge onto MA-140 S/County St toward New Bedford. Make a left on Kempton Street. Total travel time is about 1 hour.



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. Plymouth is a quaint seaside town with 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 on the Mayflower. It is hard to imagine what kind of country America would be today if those 102 brave Pilgrims hadn’t decided to leave England for a new life across the Atlantic.

See also
Boston, Massachusetts 4K Aerial Drone Footage


Nowadays, the town of Plymouth mainly caters to tourists and is a great place to come with the whole family. Besides the celebrated Plymouth Rock (which is said to be the landing site of the Mayflower but that’s not set in stone… pun intended,) visitors can also visit a replica of the Mayflower at State Pier, experience Plimoth Plantation for a glimpse into the lives of the early settlers, or stop into the Mayflower Society House (across the street and around the corner from Plymouth Rock) to learn more about the descendants of the Mayflower, register yourself as a descendent, or tour the grounds of the historic 18th century mansion. If you haven’t caught on, the town of Plymouth is centered around Pilgrims and their impact on modern-day America. It is a nostalgic place that makes for a fun and educational day trip for the entire family.


Driving from Boston: Follow the I-93 toward Quincy, merge onto RT-3 S and follow it for approximately 37 miles. Merge onto US-44 E/Samoset St via exit #6A toward Plymouth CTR. Turn right onto Court St/RT-3A.



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. Look out from Bearskin Neck at America’s most painted building, Motif No. 1. Painted depictions of the red fishing shack have shown up around the world, and has even been featured on 2002 U.S. postage stamps. The iconic structure is located at Bradley Wharf just feet from Rockport Harbor.


America’s only surviving twin lighthouses from 1861, located on nearby Thatchers Island, can be viewed from Atlantic Road at Land’s End. The Straitsmouth Island Lighthouse is smaller, but equally as handsome, and can easily be viewed from the tip of Bearskin Neck in downtown Rockport. There are plenty of art galleries and shops located along Bearskin Neck and Main Street. The Kaihlanen Gallery (61 Bearskin Neck) is particularly delightful and reasonably priced. Pick up a framed whimsical Rockport landscape to take back for a friend or for your home.

See also
North End Boston Food Tour - Clam Chowder, Lobster Roll, Pizza & Cannolis | Boston, Massachusetts


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 in the warmer months. Be sure to pick up a Rockport Visitors Guide pamphlet when you arrive to read about all the accommodations and attractions in town. If you are feeling particularly lazy, or you want to propose to your sweetheart when you visit, there are two beautiful quiet beaches in town (hint, hint.)


Driving from Boston to Rockport: Follow directions to Gloucester above. In Gloucester, there will be two traffic circles (a.k.a. rotaries.) Continue straight through both circles and follow the signs toward Rockport past the second circle. The first traffic light after the second circle is Route 127 North (Eastern Avenue) on which you should turn left and follow for approximately 3 miles.



When one thinks of Salem, I’ll bet the first thing to come to mind is witches and Halloween! 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. If you’re in Salem during Halloween, be sure to bring a Halloween costume as everyone in the town dresses up and takes the holiday quite seriously. Each October Salem plays host to Haunted Happenings, a month long celebration with events including a Grand Parade, the Haunted Biz Baz Street Fair, Family Film Nights on Salem Common, costume balls, ghost tours, haunted houses, psychic readings, live music, and chilling theatrical presentations. Salem has become synonymous with Halloween and is often referred to as “America’s biggest Halloween Party.”


Did you know that Chestnut Street is America’s first planned street? Or that the House of Seven Gables is America’s oldest wooden mansion, which was made famous by Nathaniel Hawthorne’s novel (115 Derby Street,)? Or that Salem is home to the New England Pirate Museum (274 Derby Street) as well as others that feature the witch trials of 1692? If you didn’t you are not alone. Not only is Salem a picturesque seaside town, but a cultural axis of New England. A day trip to Salem is an adventure in one of America’s first cities, and an excursion you will never forget.

See also
12 Places to See in Boston


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. By educating guests about the psychology behind “scapegoating,” the museum instills social awareness and sends a strong message to people of all ages about the dangers of fear and the importance of acceptance. The displays are a bit dated but you’ll learn the history of the witch trials.


A great feature of Salem is the proximity of its attractions, and almost all of the city’s sites are close enough to walk from one to another. You cannot miss out on walking Salem’s waterfront district along Derby Street to see the Salem Maritime Historical Park, the reconstructed Friendship that is docked there, Derby Wharf, Central Wharf, and Pickering Wharf. 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. Located at 161 Essex Street, the PEM is open Tuesday through Sunday 10am to 5pm and features various maritime inspired collections from across the globe including Native American, American, Asian, and African art, photography, sculptures, journals, and more.


Driving from Boston: Follow I-95 North/Route 128, and keep left on Route 128 North after exit #44. The exit numbers will begin dropping into the twenties. Take exit#25A onto Route 114 East and follow 114 East. At the Salem line, follow the tricolor signs.

So there you have 5 awesome day trips from Boston. If the weather is good I highly recommend driving yourself like I did, so that you can explore at your leisure without worrying about group tours or bus schedules. New England holds so much history, charm and a culture all its own.

If you’ve traveled to any of these places, or have other suggestions for day trips from Boston, please leave us a comment below!

Become a member for $5/month!

Exclusive Videos & Photos ,Early Access to my YouTube Videos And more!
Leave a Reply

Your email address will not be published. Required fields are marked *

    Related Posts


    101 Countries • 1432 Cities

    Sign up to receive travel deals and all the latest news!
    Follow us