Things to Do in Bennington, Vermont
The best things to do in Bennington, Vermont, are the 306-foot Bennington Battle Monument, the Grandma Moses gallery at the Bennington Museum and Robert Frost’s grave by the Old First Church. Bennington is a town of 15,333 people, one of Bennington County’s two shire towns and the largest town in southern Vermont.
Bennington was chartered on January 3, 1749, the first of the New Hampshire Grants, and named for Governor Benning Wentworth. On August 16, 1777, American militia beat a British force sent to seize the supplies stored here, in what became the Battle of Bennington.
Bennington Battle Monument
This 306-foot stone obelisk is the tallest structure in Vermont and stands on the site of the supply depot the British tried to capture in 1777. It was dedicated in 1891 with President Benjamin Harrison on hand, and it’s the second-tallest unreinforced masonry building in the country after the Washington Monument. The observation level looks out over Vermont, New York and Massachusetts.
★ Good to know The site is open daily from late May through October. Check that the elevator to the top is running before you count on the view.
Bennington Museum
The museum on Main Street holds the largest public collection of paintings by Grandma Moses. The schoolhouse she attended was moved to the grounds in 1972. Other galleries cover early American painters, the Bennington Modernism artists of the 1950s to 1970s, including Helen Frankenthaler and Kenneth Noland, and Gilded Age Vermont. It also has a regional history research library and a walking trail.
★ Good to know Admission is free for anyone 17 and under, and the museum closes on Wednesdays outside the fall season.
Old First Church and Robert Frost’s Grave
The congregation dates to 1762, and its white Federal-style meeting house, built in 1805, faces the green in Old Bennington near the monument. Robert Frost is buried nearby in the Old Bennington Cemetery. His epitaph comes from the last line of his 1942 poem The Lesson for Today.
★ Good to know The church began a multi-year restoration in 2024, so you may see work underway on the building.
Bennington’s covered bridges
Three Town lattice covered bridges cross the Walloomsac River just outside downtown. The Silk Bridge dates to 1840 and the Paper Mill Village Bridge to 1889, and the Burt Henry Bridge carries River Road nearby. All three are an easy loop by car on the way to North Bennington.
★ Good to know The bridges are free to see; the Paper Mill Village Bridge is also known as the Bennington Falls Covered Bridge.
Old Bennington Historic District
The hilltop village around the monument and the church is a National Register historic district, known for its well-kept early houses. It’s a small place, with a population of 156, so it’s easy to walk from the church to the monument.
★ Good to know Park once near the church and walk the loop; the monument is at the end of Monument Avenue.
Also in town
Bennington Potters has made handcrafted stoneware in town since 1948, and the museum’s Across the Street display puts 34 historic photos around downtown.
How tall is the Bennington Battle Monument?
It’s 306 feet tall, the tallest structure in Vermont. It was dedicated in 1891 and marks the supply depot at the center of the 1777 Battle of Bennington.
Where is Robert Frost buried?
In the Old Bennington Cemetery, near the Old First Church in Old Bennington. Frost died in 1963.
Where can you see Grandma Moses paintings in Vermont?
The Bennington Museum on Main Street has the largest public collection of Grandma Moses paintings, plus the schoolhouse she attended.
What other Vermont towns are near Bennington?
Manchester is about 30 minutes north, and Brattleboro is east over the mountains on Route 9. See our small towns in Vermont for more.
Where to find them
- Bennington Battle Monument Monument Avenue, Old Bennington, VT 05201 Website Directions
- Bennington Museum 75 Main St., Bennington, VT 05201 Website Directions
- Old First Church and Robert Frost's Grave Route 9 and Monument Avenue, Old Bennington, VT 05201 Website Directions
- Silk Covered Bridge Silk Road, Bennington, VT 05201 Website Directions
- Paper Mill Village Bridge Murphy Road, Bennington, VT 05201 Website Directions
Plan your trip: for events and current visitor info in Bennington, see Southwestern Vermont Chamber of Commerce →
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Where to stay in Bennington
Keep exploring
Manchester, VTAbout 20 miles as the crow fliesLincoln's summer home, a mountain toll road and Orvis's hometown.Things to do in Manchester →
Brattleboro, VTAbout 32 miles as the crow fliesAn arts town on the Connecticut River with a monthly gallery party.Things to do in Brattleboro →
Woodstock, VTAbout 61 miles as the crow fliesA classic Vermont green with a conservation-history national park.Things to do in Woodstock →Also nearby: Woodstock · Rhinebeck · Middlebury