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5 Cool Massachusetts Towns to Visit

Massachusetts Towns to Visit - Massachusetts Map
Matt Claiborne
Matt Claiborne
March 11, 2022

Massachusetts has dozens of fascinating towns with long histories and unique attractions. Visit our favorite towns and explore this great state's culture and landmarks.

Top Five Massachusetts Towns

Massachusetts offers visitors diverse landscapes and fascinating history. Visit the coast and experience the state's vital ports, seaside towns, beautiful beaches, and iconic lighthouses.

Massachusetts has fostered many literary greats, and visitors can see their hometowns and the area's inspirational landscapes.

If you love shopping, dining, and cultural events like art walks and live music, you won't be disappointed in our favorite cool Massachusetts towns.


Chatham lighthouse

Chatham features beautiful beaches and a walkable downtown area. Visitors can stroll on the beach and explore the 1877 Chatham Lighthouse.

Learn about great white sharks at the interactive Chatham Shark Center.

The downtown area features enticing boutiques and great cafes and restaurants. Every night in the summer, take a seat in the grass and listen to Chatham Band.

Nature lovers can visit the Monomoy National Wildlife Refuge and discover the different habitats that make this area a vital nesting habitat for migratory birds.


Sturbridge's best landmark is Old Sturbridge Village. This is one of New England's favorite living history museums, where visitors step back in time to the 19th century.

Visitors can see the farming community and chat with costumed interpreters who describe their daily chores. Visit the bustling village center and its quaint shops. You can also see a water-powered sawmill.

Sturbridge also features Wells State Park, where you can stretch your legs on 12 miles of trails or swim in the pond.



Pittsfield in the Berkshires has it all. Visitors can visit North Street to experience live music, theater, and art. North Street has been designated a Massachusetts Cultural District and will impress you with its dynamic arts and music scene.

Pittsfield is a great destination for food lovers. Enjoy comfort food and all-American classics like cheeseburgers and pizza, farm-fresh food, or try international specialties.

Pittsfield has a vibrant bar, pub, and brewery scene with trendy lounges and one-of-a-kind cocktails.

If you want to go shopping, you'll find a mix of casual boutiques, vintage offerings, and designer labels. Find a homemade soap or a custom mountain bike.

Whatever the season, you'll find a great excuse to experience the great outdoors in The Berkshires. In spring, enjoy wildflowers as you hike. In summer, enjoy long days that last forever. Fall brings stunning foliage, and winter offers fabulous skiing and snow sports.


North Bridge

Concord offers a rich history and a picturesque setting. The scenic downtown area features antique shops located in storefronts operating for centuries.

In 1775, the "shot heard round the world" was fired on North Bridge, and the area has many Revolutionary War landmarks. Visit the Concord Museum to see Paul Revere's lantern and Thoreau's writing desk.

Thoreau fans can visit Walden Pond and Thoreau's cabin. Another literary landmark is Emerson House, Ralph Waldo Emerson's home. Finally, visit Sleepy Hollow Cemetery to see Emerson, Thoreau, Alcott, and Hawthorne's final resting site.


Newbury port is best known for its beautiful harbor, beach islands, and brick marketplace.

Newbury's protected harbor made it a vital shipbuilding and trade center. It is also the Coast Guard's birthplace. Visit the Custom House Maritime Museum to learn more about Newbury's maritime history.

There's usually a cultural event every weekend, and visitors can enjoy music festivals and art walks.

Shoppers will love the Market Square Historic District with brownstone shops and unique finds.

Plan a getaway to Plum Island or take a whale watching or sightseeing boat trip. Finally, don't miss indulging in New England's favorite tradition, eating fresh lobster al fresco.

Experience the Best of Massachusetts

Massachusetts offers beautiful vistas, history, literary inspiration, and great shopping and dining. Immerse yourself in Massachusetts's fabulous culture and stunning landscapes when you stay at one of The Berkshires hotels on your next getaway.