Tucked in the northwestern corner of Massachusetts and just a few miles from the New York state border, Great Barrington is a quintessential Berkshire County town with a long history as a summer resort and a bright future as one of the top choices for homebuyers in the second home market.
Known for its sophisticated array of restaurants and Gilded Age-era estates, Great Barrington offers year-round activities, a beautiful geographic setting, and cultural amenities that appeal to all ages. Find our answers to some frequently-asked questions on why Great Barrington is so great.
Why is Great Barrington a Top Choice for Second Homebuyers?
A Convenient Commute from Boston and New York City
For second homebuyers who focus on weekends and seasonal stays, drive time can often be a factor in where to choose a property. The good news: Second homeowners from the Boston area can reach Great Barrington in less than a 2 1⁄2 hour drive. The drive from New York City takes just under 3 hours.
Exploring the History: From W.E.B. Du Bois to "Alice’s Restaurant"
The Berkshires, and New England as a whole, is full of fascinating history–both in living memory and from centuries ago. When history buffs ask us about local history, some of our favorite stories include:
The Legacy of the Gilded Age Estates
Settled by colonists in 1726, Great Barrington is connected to American history in several key ways. The railroad came to town during the Gilded Age of the late 19th century, bringing wealthy families looking to escape the heat of the city. While many Gilded Age mansions, or “Berkshire Cottages,” have been lost to fires and more over time, the iconic Searles Castle still stands in downtown and currently serves as a private residence.
Honoring the legacy of Civil Rights pioneer W.E.B. Du Bois
The great civil rights leader and historian W. E. B. Du Bois was born in Great Barrington in 1868. He left the area at age 17 when a local scholarship, based on his standout academics at Great Barrington’s high school, enabled him to attend Fisk University.
Du Bois demonstrated a continued connection to his home town–and was gifted his boyhood home’s property by members of NAACP–later in life. His first wife, children, and other family members are buried in Great Barrington.
In 2025, a statue of Du Bois was erected in front of the Mason Public Library to celebrate his life and legacy in the town.
The Guthrie Center and 1960s Counterculture
Great Barrington entered into 1960s counterculture music history when famed folk musician Arlo Guthrie wrote “Alice’s Restaurant,” loosely based on real-life events in Great Barrington and the nearby towns of Lee and Stockbridge. Today Great Barrington is home to the Guthrie Center at the Old Trinity Church, once the home of Alice from the song and now an interfaith church and folk music performance center.
What Are the Best Things to Do in Great Barrington?
Is Great Barrington a Good Place to Live Year-Round?
Did you know that Smithsonian magazine ranked Great Barrington number one on its 2012 list of the best small towns in America? Living in Great Barrington gives residents access to amazing restaurants, food co-ops, and farmers’ markets—including the farmers’ markets hosted by Berkshire Grown, an organization that supports local agriculture.
Culture buffs flock to the Mahaiwe Performing Arts Center to see performances by such artists as banjo masters Belá Fleck and Abigail Washburn, folk icon Arlo Guthrie, and music legends Stephen Stills and Judy Collins. Berkshire Busk! offers free cultural entertainment to Great Barrington locals each summer.
Great Barrington offers hiking on Appalachian Trails in the summer and skiing at Ski Butternut in the winter. In fact, as pointed out by the Boston Globe, there are more acres of state forest in Great Barrington than residents!
Contact us today to learn more about homes for sale in Great Barrington.
