Great Barrington, MA


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Great Barrington, Massachusetts, settled in 1726, was the first U.S. city to have a lighted Main Street. Today it holds the top spot on Smithsonian Magazine’s list of “The 20 Best Small Towns in America.”

With just 7,000 residents, Great Barrington has great historical significance. It was here that American colonists first took up arms against the British, two years before the Revolutionary War began. Great Barrington also is the hometown of W.E.B. Du Bois, the civil rights leader who co-founded the NAACP a century ago. The Great Barrington community even helped pay for Du Bois’ college education.

For history hunters, a good first stop is the Great Barrington Historical Society and Museum. Permanent collections include literature, photographs, paintings, business records and furniture from important eras in local and national history. Visitors can view Native American artifacts and tour the recently acquired Truman Wheeler Farmstead. The mid-1700s house formerly belonged on one Great Barrington’s first farming settlements.

Another popular sightseeing spot in Great Barrington is Monument Mountain. Hikers who reach the 1,642-foot summit can see far into the southern Berkshire mountains and the Housatonic River Valley. The quartzite mountain has several trail loops, none more than 3 miles long, which invite visitors to explore the rugged terrain.

For less athletic sightseeing, Great Barrington visitors can enjoy a relaxing stroll along the Housatonic River Walk. This placid greenway trail follows the city’s downtown area toward the W.E.B. Du Bois River Garden Park. Here, a permanent exhibit honors Du Bois.

The Guthrie Center at the Old Trinity Church is the former home of Ray and Alice Brock. Mrs. Brock is immortalized in “Alice’s Restaurant Massacree,” the 1967 folk song written and performed by Arlo Guthrie. The 18-minute-long song was turned into a full-length movie two years later. The Guthrie Foundation is now headquartered here and frequently hosts lectures and troubadour series.

Fans of traditional theater experiences will find that the Mahaiwe Performing Arts Center fits the bill. The 1905 building is among the nation’s oldest surviving vaudeville theaters. Today the center produces operas, musicals and plays, screens classic films and hosts popular entertainers like David Sedaris.

Take a page from Great Barrington locals when shopping for antiques and other rare finds. Elise Abrams Antiques is the place to look for rare porcelain and glass pieces. The shop’s collection includes tableware and specialty items by Tiffany, Royal Crown Derby, Lenox, Wedgwood and Limoges. The Emporium Antique Center specializes in fine art, estate jewelry, costumes and pottery. Inside the 5,000-square-foot Great Barrington Antiques Center, individual dealers showcase their wares in brightly lit cubicles. Customers can browse for furniture, prints and rugs. Berkshire Home and Antiques specializes in authentic local furniture and accessories.

For an early morning or afternoon bite, head to Martin’s Restaurant on Railroad Street, where breakfast is served all day. At the dinner hour, Castle Street Café near the Mahaiwe Center serves up Mediterranean-inspired dishes and a notable list of wines. Jazz bands frequently perform here, with no cover charge for guests.