The largest town in South County became, in 1781, the first place in the United States to free a slave under due process of law and was also the birthplace, in 1868, of W. E. B. DuBois, the civil rights leader, author, and educator. The many ex–New Yorkers who live in Great Barrington expect great food and service, and the restaurants here deliver complex, delicious fare. The town is also a favorite of antiques hunters, as are the nearby villages of South Egremont and Sheffield.
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Things You Can't Miss
Old Trinity Church, immortalized in Arlo Guthrie’s “Alice’s Restaurant,” is home to a summer series with a great roster of musicians and storytellers.
Stan Tess / Alamy
At the Great Barrington Antiques Center you can browse bric-a-brac, artworks and fine antiques all in one place.
Braddock Park / Alamy
This restored, 18th-century Normandy-style barn is a country retreat a few miles from downtown. Ask about Saturday-night candlelight dinners.
Catherine Mallette/Fort Worth Star-Telegram/MCT via Getty Images
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