Southern Vermont contains the state's oldest settled towns and some of its most famous ski resorts. Bennington, near the New York border, was the site of the Battle of Bennington in 1777, a decisive Revolutionary War engagement, and is home to the 306-foot Bennington Battle Monument, the tallest structure in Vermont. Manchester, a gracious 19th-century resort town in the Taconic Mountains, has attracted wealthy visitors since the Civil War era and remains an upscale destination.
Killington, the East's largest ski resort, sits in the central-southern mountains and draws skiers from Boston, New York, and beyond. Brattleboro, on the Connecticut River at the Massachusetts border, is a quirky, arts-driven small city, the cultural heart of southeastern Vermont, with a strong independent bookstore tradition and a historically bohemian character.
Marble from the underground quarries around Danby and Proctor, some of the largest in the world, faced the U.S. Supreme Court building, the Jefferson Memorial, and the headstones in Arlington National Cemetery; Proctor was effectively a company town of the Vermont Marble Company, once one of the largest such firms anywhere. Bennington College, founded in the 1930s as an experimental school, made that town a modernist arts center.
Southern Vermont has the state's oldest towns because settlement pushed up from Massachusetts and Connecticut, and it now has some of Vermont's highest housing costs, driven by second-home buyers from New York and Boston. Bellows Falls holds one of the oldest canals in the country, built around 1802 to bypass the Connecticut River falls, and the region's covered bridges, Vermont has more than 100, are a defining tourist image.
