2 Massachusetts Towns Crowned America’s ‘Best to Visit’ in 2025

Massachusetts offers fun opportunities and attractions to visitors who are thinking of exploring the Bay State as a vacation option. Things like nature, art, music, sports, breathtaking views, and robust fall foliage are just a few of the attractions that keep visitors returning to Massachusetts year after year. The Bay State hosts several options for visitors including bustling big cities to quaint, quiet small towns. Massachusetts can accommodate any visitor from any walk of life.

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If you plan on visiting Massachusetts this year and want to explore some of the top small towns in the Bay State, look no further. U.S. News & World Report recently released a list of The Best Small Towns to Visit in the USA for 2025 and two beloved Massachusetts towns made the list.

The Evaluation Process

U.S. News evaluated places with a population of less than 50,000 people that offer a host of restaurants and attractions, plus boast picture-perfect natural beauty and a unique character all their own.

Which Massachusetts Small Towns Are Among the Best to Visit in America for 2025?

The first town on U.S. News' list is Nantucket which placed at #10 overall. Here's an excerpt from U.S. News' review of this beloved island.

This tiny island off the coast of Massachusetts is beloved by travelers for its quaint small-town atmosphere and three photogenic lighthouses. Although you'll likely want to spend most of your time with your toes in the sand (Surfside and Jetties Beach are two popular shorelines), if you do tire of the sun, head to Nantucket's Whaling Museum to delve into the island's unique whaling history.

The second and final town on U.S. News' list is another island, this time it's Martha's Vineyard which placed #23 overall. Here's an excerpt from U.S. News' review of this popular island.

Though long believed to be a vacation spot for the wealthy, Martha's Vineyard is home to numerous bed-and-breakfast accommodations, vacation rentals, boutique hotels and campgrounds that can accommodate any budget. Pristine shores outline this Massachusetts hot spot, which makes it tough to pick just one beach to bask on for the day.

 

Bonus Massachusetts Town: Author's Pick

Berkshire County isn't represented on this list so I give you my bonus pick. One town with under 50,000 residents that I would add to the list is Great Barrington. Known for its downtown culture, Great Barrington is home to many local businesses that make tourists and locals feel at home. The town has many hiking options including the popular Monument Mountain Reservation.

Great Barrington also has many music options, especially during the summer months. Whether it's the weekly Berkshire Busk events, Sounds of Summer at the Great Barrington VFW, or the downtown Gazebo concerts, the town's entertainment offerings can satisfy a variety of musical tastes.

You can't leave the beloved Berkshire County town without catching a concert, movie, or other artistic performance at the historic and award-winning Mahwaie Performing Arts Center in downtown Great Barrington. It's just the tip of the iceberg but those are a few reasons I would add Great Barrington to the list. Check out the entire list by going here.