10 Best Places to Visit in Massachusetts

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Massachusetts is made for history lovers, but it’s also home to plenty of beautiful scenery and offers lots of outdoor adventures too. Experience the best of the best by visiting these especially fabulous places.

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Boston
Downtown Boston

Boston

The largest city in New England, Boston is not only highly navigable, but it’s also clean and features an astounding number of historical sites as well as a wide array of other attractions. As the birthplace of the American Revolution, visitors have the chance to learn about Colonial history in a much more fascinating way than reading an American history book. Following the two-and-a-half-mile Freedom Trail is so much fun, it doesn’t even seem educational. Begin at Boston Commons, the camping grounds of the Redcoats, and you’ll pass the Granary Burying Grounds where you’ll find the graves of Sam Adams, Paul Revere, John Hancock and Ben Franklin’s parents. The Boston Massacre Site and Paul Revere’s House are also along the way. If history isn’t really your thing, there are lots of other things to do too, like touring Sam Adam’s Brewery, catching a Red Sox game at legendary Fenway Park and visiting the Institute of Contemporary Art, filled with contemporary artists’ explorations of the physical and unseen world, though it’s arguably more well-known for its architecture than its art.

Oaks Bluff, Martha's Vineyard
Oak Bluffs Beach, Martha's Vineyard

Oaks Bluff, Martha's Vineyard

Oaks Bluff, located on the northeastern shore of Martha’s Vineyard, is known for its unique, vibrant-colored gingerbread cottages that give the town a storybook feel. A popular weekend getaway in Massachusetts, the picturesque harbor village evolved from a mid-19th-century Methodist campground, and eventually, the canvas tents were replaced with the hundreds of tiny, elaborately decorated cottages. They became a tourist attraction in their own right in the late 19th century – many are still family-owned and passed on generation to generation. In this compact town, you can easily walk off the ferry and spend the day on foot exploring it or visiting the beach. The beaches here face into Vineyard Sound and usually have very minimal surf, which makes the water ideal for swimming or for little ones to wade in. Don’t miss taking a ride on the Flying Horses Carousel, open from Easter Sunday through Columbus Day – it’s the oldest carousel in the nation, spinning since 1876, and a national landmark.

Great Barrington and The Berkshires
The Berkshires in the Fall

Great Barrington and The Berkshires

The Smithsonian listed Great Barrington, a city of less than 10,000, as the best small town in America. Located in the Berkshires, a popular vacation area with lots of scenic beauty, particularly throughout the Taconic Mountains. Great Barrington itself offers visitors the chance to view one of the only “castles” in the country, the Searles Castle. Now a national landmark, this stunning structure modeled on the romantic French chateau-style sits in the middle of the woods and was the former home of the famous American intellectual W.E.B. Du Bois. Throughout the Berkshires visitors can enjoy some of the state’s most spectacular fall foliage, outdoor adventures and outstanding museums like the Berkshire Museum in Pittsfield, the Sterling and Francine Clark Art Institute in Williamstown and the Massachusetts Museum of Contemporary Art in North Adams, home to one of the largest collections of modern art in the United States.

Provincetown
Provincetown in Cape Cod, MA

Provincetown

One of the most charming beach towns in New England, Provincetown is located at the far tip of Cape Cod. It is famous for its jaw-dropping surroundings that include vast sand dunes and over 30 miles of beaches, as well as being a place that welcomes all types of people. It’s long-been an art colony – in 1914, artists and business people formed the Provincetown Art Association and Museum to show and collect work by local figures, and it’s also a place where people can go to let loose and be themselves without fear of judgment. Explore the colorful downtown area, which hosts everything from grand mansions and fine eateries to fabulous seafood shacks, fudge shops, art galleries and book stores, and enjoy lots of interesting people watching.

Salem
Historic New England houses along street in Salem

Salem

Salem is another one of Massachusetts’ most fascinating historic towns, home to the oldest continuously operating museum, the Peabody Essex Museum, which opened back in 1799, when museums were officially known as a “cabinet of natural and artificial curiosities.” It was a group of sea captains that founded the East India Marine Society with a specific charter provision to collect such specimens, the legacy became this fascinating museum which holds 1.8 million pieces of maritime, Asian, African, Indian, and Oceanic art plus 22 historic buildings, including the Qing Dynasty Yin Yu Tang house. Salem was the hub of the China Trade, and once one of the East Coast’s major ports, with its streets still lined by stately homes built for wealthy merchants and sea captains. It also has literary connections as the birthplace and home of Nathaniel Hawthorne, which can be toured, in addition to being the site of the infamous Salem Witch Trials, which can be experienced through re-creations today.

Salem is known as one of the most popular Halloween vacation destinations as well as a place for year-round haunted tales. The Salem Witch Walk, run by actual witches, offers tours of its spookiest sights around town, telling the story from the witches’ perspective, including a magic circle, a tour of the most haunted graveyard in America, and lessons about spells and charms.

Rockport
Rockport, MA

Rockport

One of the most beautifully charming towns in the state, Rockport sits at the tip of the Cape Ann peninsula. It offers miles of soft sandy beaches along with some of the best hiking in the Northeast. Its coastal locale also makes it great for kayaking and even scuba diving, as well as dining on tasty, fresh local seafood.

Cambridge
Cambridge

Cambridge

Cambridge is a quintessential college town and tranquil spot with its brick façades, Victorian homes, and cobblestone streets. At the heart of the city is Harvard Square, a bustling place where students and others hop between the cozy cafes and bookstores, while musicians play and artists sell their work on the streets. Visitors will also find an excellent selection of museums, like the Harvard Art Museums and the MIT Museum, as well as the Longfellow House – Washington’s Headquarters National Historic Site, the former home of American poet Henry Wadsworth Longfellow. The house was built in 1759 and served as the headquarters for General George Washington during the Revolutionary War between 1775 and 1776.

Jiminy Peak Mountain Resort, Hancock
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort, Hancock

Jiminy Peak Mountain Resort is an all-encompassing vacation destination, serving as the largest ski and snowboard resort in southern New England in the winter. In the summer, its Aerial Adventure Park offers an aerial forest rope course with elevated courses for a variety of skill levels, while the Mountain Adventure Park features a coaster where riders speed at up to 23 miles per hour as well as the opportunity for rock climbing. The resort includes the Jiminy Peak Country Inn, which features a restaurant, spa services, an outdoor heated pool as well as indoor and outdoor whirlpools, along with a variety of vacation homes.

Plymouth
Plimouth Plantation

Plymouth

The village of Plymouth was founded in 1620 and is best known as the site of the landing of the Pilgrims who were fleeing religious persecution in Britain. Visitors can view Plymouth Rock, which marks the spot of their landing – and while there is some dispute about the rock and its significance, it does represent the settlement of New England and the second permanent colony in America. But there is a lot more to see. Hop aboard the Mayflower, a full-scale replica of the ship, complete with exhibits and tours led by costumed guides. At Plimoth Plantation, a living history museum, you can see Plymouth just as it was in the 17th-century.

Sturbridge
Sturbridge Living Museum, Sturbridge, Massachusetts

Sturbridge

Visiting one of the state’s most historic towns feels as if you’re stepping into a Norman Rockwell painting. Sturbridge is home to the Old Sturbridge Village, the largest outdoor living history museum in the Northeast, offering the chance to experience life in the 1830s, complete with costumed guides. It’s easy to spend hours exploring the multitude of unique boutiques and antique shops, and at Wells State Park, just outside of town, there is a lovely pond for swimming or canoeing. Sturbridge is also a great place to stay a while, with its quaint country inns and B&Bs, as well as modern hotels and plenty of eateries.

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