Bennington is a mix of historic Vermont village (Old Bennington), workaday town (Bennington proper) and college town (North Bennington). It is also home to the famous Bennington Monument, which commemorates the crucial Battle of Bennington during the American Revolution. Had Colonel Seth Warner and the local 'Green Mountain Boys' not helped weaken British defenses during this battle, the colonies might well have been split.
The charming hilltop site of colonial Old Bennington is studded with 80 Georgian and Federal houses (dating from 1761 – the year Bennington was founded – to 1830). The poet Robert Frost is buried here and a museum in his old homestead pays eloquent tribute.
As Bennington is within the bounds of the Green Mountain National Forest, there are many hiking trails nearby, including the granddaddies of them all: the Appalachian and Long Trails.