11 Best Small Towns to Visit in Massachusetts

Stockbridge Ranked one of the Best

By Sandi Barrett, Travel Awaits
September 6, 2020

Photo Credit: John Miskis

Quaint fishing villages, gorgeous seaside enclaves, historic towns, and scenic hamlets dot the Massachusetts landscape. From the tip of Cape Cod to the top of the Berkshires, the getaway options are diverse and intriguing.

Stockbridge is the quintessential New England woodland town. Located in the Berkshires, it is home to the Norman Rockwell Museum and several estates including Chesterwood and Naumkeag.

Iconic American images from the covers of The Saturday Evening Post come to life at the Norman Rockwell Museum. View Rockwell’s work in addition to other exhibits at this treasured museum.

Stockbridge’s sprawling estates bring history to life as you stroll the grounds and explore the homes. Chesterwood is American sculptor Daniel Chester French’s home. French is best known for crafting the figure of Abraham Lincoln for the Lincoln Memorial. Naumkeag is the summer estate of Joseph Hodges Choate, former ambassador to Great Britain. It offers a variety of events, including tours, yoga, and art classes.

Here are all 11 of the best small towns to visit in the Bay State.