My Journey Through New England: 10 Day Trips From Boston That Mesmerized Me

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Jake Cain is an entrepreneur and writer from Cincinnati, Ohio. He spends his free time driving around the country in his late 90’s conversion van, affectionately known as the “Monster Van” with his wife and 3 boys.

Given its status as the state capital and a major city, Boston is the de facto cultural and economic capital of New England. Located on the shore of the Atlantic Ocean in eastern Massachusetts, there are a plethora of day trip opportunities within a range of Boston. 

If you’re interested in learning about a handful of these potential day trips from Boston, you’re in the right place. 

The Boston Harbor Islands

Boston Harbor Islands
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If you want to take an interesting day trip from Boston, but you don’t have a car, The Boston Harbor Islands might be a great choice for you. The Harbor Islands are a quick 30-minute ferry ride from the Boston harbor, and each island has a handful of fun activities.

While there are 21 islands in total, most visitors focus on a few of the largest islands. In particular, George’s Island is great for families who love to explore archaeological sites and then have a picnic. 

On George’s Island, you’ll find a massive Civil War-era prison complex that’s maintained as a museum. The complex covers most of the island, and there’s plenty of nooks and crannies to explore over the course of a day. 

There’s also a concession stand near the ferry dock on the island. Make sure to protect your food from the patrolling seagulls!

As with many areas near Boston, you’ll need to visit in the summer to enjoy the islands to their fullest potential. 

Tanglewood, Massachusetts

Boston Symphony Orchestra
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If you love listening to classical music in a bucolic New England town, it’s hard to beat Tanglewood. Tanglewood is a couple of hours from Boston, and it’s located near Sturbridge. 

Home to the Boston Symphony Orchestra, Tanglewood is a wonderful destination for dining and live music in the summertime. If you don’t have tickets for an orchestra show, you can frequently catch them practicing in the Seiji Ozawa Hall in the early afternoon. 

Families will also enjoy visiting the local gardens, art galleries, and restaurants with typical New England fare. Everything in Tanglewood is child-friendly, so you won’t need to worry about having difficulty in bringing your strollers around.

You’ll need a car to get to Tanglewood. While there is a Greyhound bus that runs from Boston, it doesn’t run frequently enough for a day trip.

Amherst, Massachusetts

Amherst, Massachusetts
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Amherst is a quaint New England town that bustles with activity. Located three hours west of Boston near Springfield, Amherst is the town that embodies the wooded and intensely political region of western Massachusetts. 

Amherst has something for everyone. The town square has a number of interesting shops, galleries, historical landmarks, and tasty restaurants from all over the world. Unlike other day trips from Boston, you’ll find something to do in Amherst during any time of the year. 

The University of Massachusetts Amherst campus is the cultural center of Amherst. Known fondly by locals as “Zoo Mass”, the university is home to an endless number of musical performances, theater, lectures, and political activity. You’ll also find a handful of dive bars and downmarket food shops. 

Be sure to visit it to get a sense of Amherst’s most lively area. Amherst’s town center is family-friendly, but be aware that the rowdy students come out at night.

You can reach Amherst by bus or by car. There’s plenty of free parking, and the bus tends to be crowded, so driving is preferable.   

Provincetown, Massachusetts

Provincetown, Massachusetts
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If you’re into flamboyant theater, bicycling, and dining out at fancy and trendy restaurants, Provincetown is a great choice for a summertime day trip. Referred to by the locals as “P-town”, Provincetown is located on the tip of Cape Cod, surrounded by the Atlantic ocean on three sides.

Provincetown is known as a nexus for the New England gay community, but everyone is welcome to enjoy the town’s many tourist attractions. In the summer, many people enjoy biking around the town’s many paths through the wilderness or along the beach. 

For art lovers, Provincetown has many small galleries and artist spaces, many of which are open to the public for free.

Feel free to drop into a roadside production of a Shakespearean classic — or grab tickets to a fancier matinee at one of the many playhouses in the town. Afterward, you’ll enjoy sitting down at an oyster bar, lobster shack, a wine bar, or French bakery. 

You’ll need to hop onto the ferry in Boston Harbor for about two hours to reach Provincetown. There are only a few ferry departures from each dock per day, so plan accordingly. 

If you decide to drive or take a bus to Provincetown, it’ll take you a very long time — potentially as long as four hours.  

Hyannis, Massachusetts

Hyannis, Massachusetts
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Located two hours south of Boston, the town of Hyannis is an aquatic New England treasure with a lot of life. In Hyannis, you’ll find New England restaurants, small artisan shops, art galleries, and numerous museums from the 1800s. 

Many families with small children enjoy visiting the Whaling Museum, which also serves as a general museum for everything nautical. History buffs will enjoy the Hyannis JFK Museum, which contains an abundance of memorabilia and historical artifacts pertaining to the late president. 

If you’re more interested in science than history, head over to take a tour of the legendary Woods Hole Oceanographic Institute, which you may know from the movie Jaws. If fishing is more your thing, head over to the recreational fishing dock and rents a boat for the afternoon.

You can reach Hyannis by car or by train from Boston. 

Gloucester and Rockport, Massachusetts

Gloucester and Rockport, Massachusetts
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Gloucester and Rockport are two adjacent oceanside towns on the north shore of Massachusetts, roughly an hour’s drive from Boston. Gloucester and Rockport are known for their wonderful fresh seafood restaurants, art galleries, rock beaches, breweries, and bookstores.  

If your family enjoys dropping by artisan workspaces to talk with artists and sculptors, Rockport is the place to be. Aside from the artist’s colony in Rockport, you can also find artisan workspaces in downtown Glocester too. 

Be sure to also check out Bearskin Neck in Rockport, where you’ll find a walkable area with live music, great restaurants, souvenir shops, ice cream stores, and sculpture galleries. There’s also a beautiful overlook onto the Cape Ann Bay at the tip of the neck, so bring your camera. 

If drinking a beer is more your thing, Gloucester’s numerous seaside breweries will be right up your alley. Likewise, if you want to take a quick fishing trip or learn how to shuck an oyster, Gloucester’s fishing docks are the place for you.

Both Gloucester and Rockport are served by the commuter rail, which you can board at Boston’s North Station. Be aware that the touristy area of Rockport is a 20-minute walk from the train station, however. 

If you decide to drive your car, you’ll have an easy time finding free parking in either town. 

Portsmouth, New Hampshire

Portsmouth, New Hampshire
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For individuals or families seeking a pleasant and inexpensive New England town with a compelling conflux of New England cultures, Portsmouth is a fun place to spend a day. 

Located an hour and a half north of Boston, Portsmouth has something for everyone. If you’re interested in fine dining, Portsmouth has plenty of options. If you’re more interested in a casual bite or a mug of chowder, you won’t be left wanting. 

Portsmouth’s many beer breweries and coffee roasting shops are equally enjoyable. Take a brewery tour, or, if you prefer, a tour of a coffee roastery. In the summer, be sure to check out the free concerts in the central square. 

If you’re a motorcyclist, you’ll be in good company in Portsmouth. Many motorcyclists and motorcycle clubs meet in the central square to enjoy a cup of coffee in the sun while catching up. 

While it’s possible to take a bus from Boston to Portsmouth without much trouble, it’s easier to drive there in your car. Parking in Portsmouth is plentiful and free, but you may need to walk 10 or 15 minutes from your car to get to the bustle of the town square.

Providence, Rhode Island

Providence, Rhode Island
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Providence is New England’s second city, and it’s full of cultural and culinary delights, which make it a great choice for a day trip. Located an hour and a half south of Boston, Providence is well-known for its exquisite Italian food scene, which is concentrated around Atwell Avenue. 

Families will also enjoy walking around the Federal Hill historic district, which contains the Rhode Island statehouse as well as a number of trendy gastropubs. Be sure to also check out Waterplace Park, which is home to lovely live music performances in the spring and summer.

For people looking to catch a show, Providence is also home to several theaters. Similarly, if you want to check out a few museums, there are a few notable ones in Providence, most of which are located around the Enlightenment-era Old State House. 

If you don’t feel like driving, you can take a train from Boston to Providence very easily. If you decide to drive, you will probably need to pay for parking somewhere downtown in Providence, as street parking is limited. 

Newport, Rhode Island

Newport, Rhode Island
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Newport is a small yet touristy town located a little over two hours south of Boston. Because it’s on a small island connected by several bridges, Newport is a wonderful place to spend an afternoon sailing, hanging out by the beach, or fishing.  

The largest tourist attractions in Newport are the Breakers, a collection of early 20th-century mansions constructed on a cliff overlooking the ocean. Each mansion is several stories high, and several of them have been converted into museums that are open to the public. If you’re a fan of the Vanderbilts or other Gilded Age dynasties, you’ll love touring through the Breakers. 

For foodies, Newport has a small handful of delicious upmarket restaurants. However, Newport’s real charm is in its standard New England seafood restaurants, which are affordable and delicious. 

For people who love traditional New England delicacies like saltwater taffy, clam chowder, fried clams, hot fudge, and freshly churned ice cream, Newport is hard to beat. 

While the local wine scene is limited due to the harsh New England climate, it’s also fun to visit Caroyln’s Sakonnet Vineyard for a wine tasting in the summer.  

Portland, Maine

Portland, Maine
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Portland is the jewel of southern Maine, and it’s scarcely a two-hour drive from Boston. In Portland, you’ll find a bevy of excellent beer breweries, many wonderful pizzerias, and a smattering of New England culture.

For a day trip, the best part of Portland is the Old Port area. It’s easy to lose a few hours walking up and down the area’s hills, all of which are flanked by red-brick buildings from the turn of the 20th century. 

Portland has all of the typical New England dishes which you’d expect, but it also has a few specialties. In particular, you’ll want to eat some freshly-caught lobster while you’re in Portland. Likewise, the city’s pizzerias are exceptionally good, though there’s no special style or traditional set of toppings. 

In the summer, walk through Monument Square to get a taste of local history and foods produced by local farmers. 

Thompson’s Point is also great to visit if you like to grab a beer at a brewery or a wine from a local vineyard. If museums are more your thing, drop by the Portland Museum of Art, but be aware that you’ll need other activities to fill your day. 

Now that you’re up to speed on a handful of the best day trips from Boston, you can start to plan your trip. Keep in mind that most of the day trips we’ve proposed are going to be more enjoyable in the summer than in the winter. 

Likewise, remember that you may not always need a car to go on a day trip. If you need ferry tickets, you don’t necessarily need to buy them ahead of time. The same goes for the areas which are accessible via the train. 

Enjoy the beautiful offerings of New England!

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