5 Day Trips from Boston

I advise renting a car to leave Boston and explore these day excursions from Boston. Rockport is where I got engaged and so it will always hold a spot in my heart, but Gloucester, New Bedford, Plymouth, and Salem are all places to experience. Wherever you opt to stay, eat, and perform , New England has something for everybody!


You will be brought by A pleasant driveway from Boston to Gloucester- an English settlement based which makes it older by 7 years. The longstanding heritage in fishing and shipbuilding of gloucester began in the early 1700’s. The harbor is faced by the Gloucester Fishermen’s Memorial on Stacy Boulevard and is dedicated to the hundreds of local fishermen who lost their lives at sea. By driving or walking west of the statue onto Stacy Boulevard, people can visit the Fisherman’s Wife Statue in their way to the Stage Fort Park Welcoming Center.

New Bedford

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


Gloucester provides its guests with an array of things to do while it’s fishing, snorkeling, kayaking, whale watching, or just relaxing with the harbor that is gorgeous. Whale season normally lasts from late April to late October, and booking in advance is advised during the summertime.



Northeast of Cape Ann Brewing Co. is the Cape Ann Museum (27 Pleasant Street), which is home to an astonishing collection of maritime artwork. It’s a reflection of the pride. Gloucester is a day excursion that the entire family will adore. A ideal mix of relaxation and adventure.

Driving from Boston: Follow either Interstate 93 or Route 1 to I-95 North (I-95 North and Route 128 are the same.)

Practice I-95 North/Route 128 toward Maine and New Hampshire and stay left before exit #45.

New Bedford sits 50 miles south of Boston and is often referred to as the whaling city because it had been the most rewarding fishing port and main resource for whale oil supply of America. Whaling shaped New Bedford’s history, also at the first 19th century immigrants from the Cape Verde Islands began arriving in New Bedford from the dozens.

From the 20th century, Cape Verdeans were arriving from the hundreds to function as crewmen on Massachusetts’s whaling boats. Keeping with the city’s theme, guests can have a look at the New Bedford Whaling Museum (18 Johnny Cake Hill), also a 107-year-old institution which holds an extensive collection of whaling artifacts, books, art, boat designs, harpoons, and whale skeletons. Marvel in the 37-foot long skeleton of a humpback whale and find out about its species’ life cycle in sea, or just enjoy the numerous ocean portraits.

Once you are finished with the museum, have a load off and enjoy a number of New England’s famous seafood in one of the seaside restaurants along Rodney French Blvd.. Then, relive your high school see The Seaman’s Bethel and American literature days – the whaleman’s chapel said in Melville’s Moby-Dick. Now it’s a non-denominational chapel and memorial for whalemen who’ve lost their lives in sea (15 Johnny Cake Hill). New Bedford’s cobblestone streets give it an old world sense and will transport you from when fishermen controlled the ocean and the land.

Driving from Boston: Practice I-93 South to I-90 West/Quincy/Worcester, Also Stay left.

Take the I-93 South. Merge onto MA-24 South toward Brockton. Take exit #12 to blend onto MA-140 S/County St toward New Bedford. Make a left on Kempton Street. Total journey time is approximately 1 hour.

Around 40 miles from Boston Across the South Shore of Massachusetts Stays Historical Plymouth.

5 Day Trips from Boston

Considered”America’s Home Town,” Plymouth is where the Pilgrims landed on the Mayflower in 1620, and where the very first Thanksgiving feast took place involving the Wampanoag Indians and the Pilgrims in 1621. Plymouth is a seaside town with a history.

Not many people realize that Marilyn Monroe, Presidents George Bush and son George W. Bush, Governer Sarah Palin, Alec Baldwin, Richard Gere, Clint Eastwood, along with more than ten thousand other famous (and non-famous) Americans are the immediate descendents passengers who landed on the Mayflower. It’s really tough to envision what sort of nation America will be today if those Pilgrims had not chose to leave England for a new life across the Atlantic.

5 Day Trips from Boston

Today, the city is a great place to have the whole family and of Plymouth largely caters to tourists. Besides the mythical Plymouth Rock (which can be reportedly the landing site of the Mayflower but that’s not set in stone… pun intended,) visitors can also visit a replica of the Mayflower in State Pier, experience Plimoth Plantation for a glimpse into the lifestyles of the early settlers, or stop into the Mayflower Society House (across the street and around the corner in Plymouth Rock) to find out more about the descendants of the Mayflower, enroll yourself as a descendent, or tour the grounds of the historical 18th century mansion. Then the city of Plymouth is centered around Pilgrims and their impact on America, When you haven’t caught on. It’s a nostalgic place which makes for an enjoyable and educational day excursion for the entire family.

5 Day Trips from Boston

Driving from Boston: Practice the I-93 toward Quincy, merge onto RT-3 S and follow it for approximately 37 miles.

5 Day Trips from Boston

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 into love with Rockport. Is it the place where I proposed for my fiancé, it’s an ideal daytrip to get out of the city and into a frame of mind. Rockport takes you back to a place when life was easier in time. Look out from Bearskin Neck in America’s most painted building, Motif No. 1. Painted depictions of the red fishing shack have demonstrated upward round the world, and has even been featured on 2002 U.S. stamp stamps. The structure is situated in Bradley Wharf just feet.

America’s only surviving twin lighthouses in 1861, situated on neighboring Thatchers Island, could be viewed from Atlantic Road in Land’s End. Even the Straitsmouth Island Lighthouse is equally fine, although somewhat bigger, and can be considered in the suggestion of Bearskin Neck in downtown Rockport. There are plenty of stores and art galleries situated along Bearskin Neck and Main Street. Even the Kaihlanen Gallery (61 Bearskin Neck) is particularly delightful and reasonably priced. Pick up a Rockport landscape that is framed to return for your house or for a friend.

Rockport is a city located around fishing and fishing in Cape Ann. Kayaking, whale-watching excursions, and fishing boat charters are all popular activities in the summer months.  Be sure to pick up a Rockport Visitors Guide pamphlet if you arrive to read about all of the accommodations and attractions in the city. If you are feeling particularly lazy, or you need to propose to your love when you see, you will find two lovely quiet beaches in the city (hint, hint.)

Driving from Boston to Rockport: Follow directions to Gloucester above.

5 Day Trips from Boston

In Gloucester, there will be two traffic circles (a.k.a. rotaries.) Continue straight through both circles and follow the signs toward Rockport beyond the next circle. The first traffic light after the next ring is linking 127 North (Eastern Avenue) on which you ought to turn left and follow for approximately 3 miles.

I will bet the first thing to come to mind is witches and Halloween when one thinks of Salem! However, Salem is considerably more than the usual blip in American history. It’s a place that is home to several of America’s treasures.  Be sure to make a Halloween costume up if you are in Salem through Halloween and takes the holiday 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 street that is projected? Or that the House of Seven Gables is America’s oldest modular home, which has been 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 which feature the witch trials of 1692? You’re not alone, if you didn’t. Not only is Salem a picturesque seaside city, but also a cultural axis of New England. A day visit to Salem is an experience of America’s primary cities.

Start off the day in the Salem Witch Museum (19 1/2 Washington Square North).

The museum has been founded in 1972 and has since showcased the entire history and origins of witch hunts needless to say, the events of the notorious Salem witch trials and in the world. By educating guests about the psychology behind”scapegoating,” the museum instills social consciousness and sends a strong message to people of all ages about the risks of fear and the value of acceptance. The screens are somewhat dated but you will learn the background of the witch trials.

A excellent feature of Salem is the proximity of its attractions, and the city’s sites almost all are near enough to walk to the next. You Cannot miss out on walking Salem’s waterfront district across Derby Street to Find the rebuilt Friendship That’s docked there, the Salem Maritime Historical Park, Derby Wharf, Central Wharf, along with Pickering Wharf. Finz Seafood and Grill (76 Wharf Street) is an Perfect spot to stop for a tasty lunch together Salem’s Pickering Wharf. Complete at Salem by seeing the Peabody Essex Museum. The PEM is available Tuesday through Sunday 10am to 5pm and features marine motivated collections from throughout the world including American, Asian, and African American art, Native American, photography, sculptures, newspapers, and much more.

Driving from Boston: Practice I-95 North/Route 128, and Also keep left on Route 128 North after exit #44.

5 Day Trips from Boston

The exit numbers will start dropping into the temple. Take exit#25A onto Route 114 East and follow 114 East. In the Salem line, follow the tricolor signals.

So there you have 5 awesome day excursions from Boston. In case the weather is good I highly advise driving yourself like I did, so which you could explore at your leisure without worrying about bus schedules or set tours. New England holds so much history, charm and a culture all of its own.

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