Bennington
Rich History Among the Taconic Mountains
Bennington, Vermont
Bennington is Vermont’s oldest town. The state’s tallest man-made structure, the Bennington Battle Monument, spears the sky at 306 feet, commemorating the town’s history as the site of a pivotal Revolutionary War battle. Nestled in the southwestern corner of the state in a region known as the Shires of Vermont, the Green Mountain State’s rich history comes alive in Bennington.
Top Attractions
A rich vein of history runs through Bennington, from covered bridges dating back to 1840 to the world’s largest collection of Grandma Moses art. Nearby, explore a museum, mansion, and a country club.
Bennington Museum
The world’s largest collection of Grandma Moses folk art, along with other historically significant Americana, is housed here.
Read More about Bennington MuseumRead MoreWalloomsac Covered Bridges
Southern Vermont is rich with history, and its covered bridges are no exception. The Burt Henry, Silk Road, and Paper Mill covered bridges were built in 1840.
Robert Frost Stone House Museum
U.S. Poet Laureate Robert Frost lived in this house for nine years, during which time he wrote “Stopping By Woods on a Snowy Evening.”
Read More about Robert Frost Stone House MuseumRead MoreBennington Battle Monument
At 306 feet, this monument commemorating a pivotal Revolutionary War victory is Vermont’s tallest structure.
Read More about Bennington Battle Monument Read MoreOld First Congregational Church
Gathered in 1762, Vermont’s oldest Protestant church is an architectural and historic landmark.
Read More about Old First Congregational ChurchRead MorePark-McCullough Historic Governor’s Mansion
A well-preserved 35-room Victorian mansion set on 200 acres of grounds.
Read More about Park-McCullough Historic Governor’s MansionRead MoreMount St. Anthony Country Club
Golf course, wedding venue, and country club in southern Vermont.
Read More about Mount St. Anthony Country ClubRead MoreBennington Theater
The Bennington Theater offers a diverse lineup of events in addition to live performances, including trivia, interactive audience experiences, and educational programming, in the heart of the Shires region.
Read More about Bennington TheaterRead MoreDowntown Bennington
A visit to Bennington offers an urban feel set amidst the beauty and historic charm of southern Vermont.
Attraction Spotlight
Bennington Battle Monument
Vermont’s tallest structure pierces Bennington’s skyline at 306 feet, commemorating a pivotal Aug. 16, 1777 Revolutionary War victory as Vermont, New Hampshire, and Massachusetts soldiers battled British troops charged with stealing provisions. Visitors can also explore a gift shop and picnic area.
Event Spotlight
Garlic Town, USA
Annually on Labor Day Weekend
Bands, beer, and food trucks plus a curated group of over 120 vendors await at this time-honored New England traditional event. Sample garlic-infused maple syrup, garlic fries, and, of course, lots of locally grown Vermont garlic at this event that started as a garlic-focused farmers market.
Transportation Options
For Bennington
Airport
William H. Morse State Airport
1563 Walloomsac Road
Bennington, VT
Local Transportation
- Car Rental services: Enterprise
- Taxi Service and/or Rideshare: Walt’s Taxi, JEC Personal Transport, Monument Taxi, Happy Cab
- Bus services: Green Mountain Express
Discover More
Trip planning resources with Bennington’s local downtown organization.
Vermont Begins Here about Discover More