Historic Downtown


Seen from above, a tall, slender stone monument raises above the trees.
Group of people take a selfie in front of a sign that reads Take a stinkin' selfie.

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.

Downtown Bennington

A visit to Bennington offers an urban feel set amidst the beauty and historic charm of southern Vermont.

Seen from above, a tall stone monument surrounded by forests on a sunny day.

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.

People crowd around a festival, including a colorful bounce house and vendor stalls, in a bustling downtown.  
A person works a booth while wearing a crown with heads of garlic on it.

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.

Eat, Shop, and Stay in Bennington







Transportation Options

For Bennington


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 
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Discover More

Trip planning resources with Bennington’s local downtown organization.

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