The 7 Can't-Miss Towns In Massachusetts

With over 1,500 miles of shoreline, mountain ranges like the Appalachians and Berkshires, and a rich history of art colonies, Massachusetts has understandably become a favorite vacation spot for travelers countrywide. Much of the state’s beauty, however, lies in its smaller towns, scattered throughout Cape Cod, the Berkshires, and other tranquil areas. If you are looking to visit some of Massachusetts’ most impressive destinations, these seven small towns should be at the top of your list.

Provincetown

At the northernmost tip of Cape Cod, Provincetown holds the title of the oldest continuous art colony in the United States, making it a must-visit for art lovers. Travelers can start their weekend at the Provincetown Art Association and Museum (PAAM), a cultural institution that is over 100 years old and exhibits over 3,000 pieces in its permanent collection. Commercial Street is another artistic highlight, lined with more than 40 galleries, including the well-regarded Bowersock Fine Art Gallery, which has been showcasing work since 2004. Make sure to spend some time at one of Provincetown’s beaches as well! Herring Cove Beach is a great option for a beautiful sunset, with the sun setting straight over the Atlantic.

Nantucket

Accessible by ferry, Nantucket is an adorable island town that is popular for both its beaches and historic landmarks. The island is home to three lighthouses, including Brant Point Lighthouse, one of the oldest in the United States. Dating back to 1746, the lighthouse has been rebuilt several times, with the current structure standing for more than 110 years. After visiting some of the island’s historic lights, head over to the Whaling Museum, where you can learn about the region’s whaling heritage over the centuries in its nine galleries. Travelers will also enjoy unwinding on Jetties Beach, a wide and flat beach with shallow waters that is perfect for families with young children. Several events take place on this beach during the summer as well, so keep your eye on the calendar!

Northampton

Nicknamed “Paradise City,” Northampton is rich in greenways and parks, with about 70% of its residents living within easy reach of a bike path or trail. Travelers wanting to get some exercise can enjoy a bike ride along the MassCentral Rail Trail, a route that will eventually extend 100 miles, connecting Northampton to Boston. About 7 miles run through Northampton itself. Ranked as a top art destination by AmericanStyle Magazine, the town also has an exciting art scene. Travelers can experience this art at institutions such as the Smith College Museum of Art, which has four floors of art to explore, or at a local gallery like the R. Michelson Galleries, the largest commercial gallery in Western Massachusetts.

Rockport

Less than an hour north of Boston, many Bostonians head to Rockport for the weekend to appreciate its seafood, sailing, and art scene. Travelers looking for the true coastal experience can book a charter with Rockport SeaVenture. This local agency takes passengers out around the harbor on a 90-minute tour, showing them the local wildlife and landmarks and teaching them how to catch lobster! After a morning of lobster catching, grab lunch at Roy Moore Lobster Company. This beloved father and son-owned restaurant serves fresh lobster, lobster rolls, and other mouthwatering seafood dishes. If you enjoy admiring art, make sure to stop by the Rockport Art Association & Museum, which preserves and exhibits over a century of art from around Cape Ann.

Concord

As the birthplace of the American Revolution, Concord is one of the best places in Massachusetts for a history-filled vacation. The Minute Man National Historical Park is the perfect place to begin, featuring battlefields and historic sites where the revolution began in 1775. Meanwhile, the Concord Museum houses some of Concord’s most impressive artifacts, such as the lantern that Paul Revere placed in Boston’s Old North Church steeple in 1775 and the writing desk where Thoreau composed Walden. Beyond Revolutionary War history, the town also features the Ralph Waldo Emerson House, where the renowned poet and philosopher lived starting in 1835, writing pieces like Nature in 1836 and Self-Reliance in 1841.

Stockbridge

Situated in Massachusetts’ picturesque countryside, Stockbridge is the ultimate town for those wanting to experience the Berkshires region. Throughout town, you will find numerous historic buildings, many of which date back to the 18th and 19th centuries. The Red Lion Inn, for example, dates back to 1773, continuing to operate as a cozy inn today. Book lovers can also stop by the Stockbridge Library, one of Western Massachusetts’ oldest libraries, equipped with a historical room, museum, and research center. To explore the town’s natural beauty, spend an afternoon at the Berkshire Botanical Garden, one of the northeast’s oldest garden displays, spanning roughly 24 acres and featuring dozens of display areas. The Laurel Hill Association offers three trails spanning 460 acres, making it another key highlight.

Gloucester

With seven beaches and abundant whale-watching opportunities, Gloucester is another popular weekend destination, particularly for Bostonians, thanks to its close proximity. Good Harbor Beach is a great spot for sunbathing and swimming, featuring white sandy shores and a nearby island accessible at low tide. Travelers hoping to spot some marine life can reserve a tour with 7 Seas Whale Watch, which will take passengers out to sea to spot creatures like humpback whales, minke whales, finback whales, dolphins, and seals. If all of the swimming and whale watching have made you hungry, grab a bite at Seaport Grille, a waterfront restaurant on the harbor that serves surf and turf, American, and Italian cuisine.

Final Thoughts

These seven towns are just the beginning of Massachusetts’ beauty. There are so many other towns to consider adding to your list, such as Oak Bluffs, Lenox, and Williamstown. However, the towns mentioned above provide a solid mix of beaches, hikes, Revolutionary War history, and art museums—everything you need for a well-rounded vacation. So don’t let the summer slip away! Take advantage of the beauty that awaits in Massachusetts and get ready to have a memorable time.