3 Berkshire Towns Make ‘Best Place To Retire’ List In Mass.

Our beautiful Berkshires are famous for beautiful hills, colorful fall leaves, and a relaxed way of life. Three towns in the county made the 2025 list of the best places in Massachusetts to retire: Lenox, Williamstown, and Great Barrington.

Lenox

Lenox is perfect for people who love nature and culture. It has a median age of 64, so many neighbors are retirees too. You can hike or bike in October Mountain State Forest, the biggest state forest in Massachusetts, or visit The Mount, the former home of writer Edith Wharton. Lenox also has amazing restaurants and is home to Tanglewood for a summer night out on the lawn to enjoy a concert. Houses had a median price of $549,000 in September 2025.

Williamstown

Williamstown is a beautiful spot, peaceful as well, with Williams College right in the center. Retirees can take classes there or play on the Taconic Golf Club, one of the best courses in the state. The fall colors are amazing, and homes cost around $525,000 (August 2025). My favorite driving spot is alongside Rte 43 and the Green River.

Great Barrington

Great Barrington - South County's center. Main Street is full of shops, cafés, and restaurants. You can kayak on the Housatonic River, swim at Lake Mansfield, or enjoy shows at the Mahaiwe Performing Arts Center. Even though it’s small - about 7,000 people, it has everything you need. Median home prices were $710,000 in September 2025. -worldatlas.com

These three Berkshire towns give retirees pretty views, friendly neighbors, fun things to do, and good healthcare nearby at Berkshire Medical Center.