Located in the extreme southwest of the state of Vermont, near the borders of New York state and Massachusetts, Bennington is a small- to medium-sized town as far as Vermont towns go, yet nonetheless offers plenty of allure. Bennington is especially popular with summer tourists visiting the New York, Boston and Montreal areas.
Bennington is a classic Vermont country town having a compact, walkable downtown area and plenty of interest in the surroundings. Its claim to fame is its five covered bridges, notable college and contribution to the Revolutionary War, to which the Bennington Battle Monument and Bennington Museum provide further insight.
You should be able to visit much of what Bennington has to offer over a weekend. The town center and attractions can easily be done in a day, but Bennington’s best showing is its surrounding green mountains and valleys.
Highlights
The Bennington Battle Monument: this 300-plus foot monument was built in the late-19th century and is dedicated to the famous Battle of Bennington during the Revolutionary War in 1777.
Bennington Museum: located on Main Street, features changing exhibits, fantastic collections of American furniture and paintings, lots of military history, and toy dolls.
The Vermont Covered Bridge Museum: on Gypsy Lane lends fascinating insight into covered bridges through dioramas and interactive exhibits.
Hemmings Motor News Car Lover’s Oasis: is a real working, old-style service station on West Main Street with a display of fine old vehicles.
Old First Church: on Monument Avenue is the oldest church in Vermont, displaying post-colonial architecture.