Nearby city: Lebanon, N.H.
Population: 2,393
Median family income: $53,949
Runner-up: North Bennington

This historic railroad town is an unincorporated village within Hartford, Vt., and boasts a wide variety of architectural styles, from the late 19th and early 20th centuries, from Victorian to Greek Revival. The village has a rich cultural community, thanks to a regional theater, a writer’s center, the Main Street Museum, and a strong local music scene. Nearby colleges in the area include Bennington, Middlebury, and Dartmouth. Nestled at the confluence of the White and Connecticut rivers, the area is ideal for lovers of outdoor sports, with skiing and snowboarding during the winter and golf and hiking trails during the summer.