Like all towns in Vermont, Bennington is small. Lesser known than its peers, Burlington and Brattleboro, Bennington is often called the “gateway” to Vermont – a position that appeals to some, but leaves others unconvinced.
Bennington sits in the southwest corner of Vermont and is, notably, the closest part of Vermont to New York. Only 40 miles from Albany, many of Bennington’s residents commute daily to New York’s capital, as well as to Williamstown, just over the border in Massachusetts. Promoted heavily as “the real Vermont,” the area – not surprisingly – is often considered slightly lessauthentic by natives living deeper within the state.
The town of Bennington is composed of three original villages: Old Bennington, Bennington and North Bennington. Originally chartered in 1749, Bennington today has fewer than 16,000 full-time residents. BenningtonCounty, which covers the 575 square miles directly adjacent to both New York and Massachusetts, has a total population of 35,000 people and is divided into two distinct areas, the North Shire (county seat) around the town of Manchester, and the South Shire, of which Bennington is the center.
Together, this area stretching between the Taconic Mountains and the Green Mountains is promoted as the “Shires of Vermont,” and includes many smallpostcard-worthy towns and villages along historic Route 7A.
Even without the quaint old-fashioned name, the area’s ski resorts, high-end shopping outlets, covered bridges and Revolutionary War historyall guarantee that a steady stream of visitors will pass through this corner of the Green Mountain State.