Bennington is southern Vermont with a revolutionary streak: old houses, a tall stone monument, a compact downtown, and hills rising toward both the Green Mountains and the New York line. It is less polished than Manchester and less bohemian than Brattleboro, which is part of its appeal.
The essential stop is Old Bennington, where the Bennington Battle Monument rises above a village green of Federal-era houses and the Old First Church. Down the hill, the Bennington Museum gives the town real cultural weight, especially for folk art and regional history.
Bennington also has a literary shadow. Shirley Jackson lived in North Bennington, and Robert Frost's former Shaftsbury home is a short drive north. That mix of pretty New England surfaces and slightly uncanny undertones suits the place well.