Cultural Attractions

Built to commemorate the Patriot victory at the Battle of Bennington during the Revolutionary War, the Bennington Monument is the most visited historic site in the state of Vermont. Take an elevator ride up and enjoy the magnificent views of the surrounding area.

Largest collection of Grandma Moses art and memorabilia available to the public. Fine collections of paintings, pottery, fine furniture, and historical objects that evoke the rich heritage of Vermont.

A rich, permanent collection of dolls and dollhouses, from simple Cape Cod houses to elaborate Victorian houses. There also are trains and trucks on display as well as educational toys.

This is an old car hobby museum housed in an old-fashioned, full service Sunoco station. Featuring a huge collection of automative items including models, pedal cars, and artwork, as well as fun reproduction signs. Grab a cup of coffee at our cafe while you get a fill up and window wash. Be sure to catch one of the summer weekly cruise-ins, featuring an interesting assortment of vintage cars on Thursday evenings!

This was Robert Frost’s residence from 1920 to 1929 when he composed many of his literary masterpieces, including “Stopping by Woods on a Snowy Evening”. Located on Route 7A in Shaftsbury, only minutes away from his gravesite in the Old First Church Cemetery in Old Bennington, this historic house was built in 1769. Visit the house and stroll the beautiful grounds featuring some of Frost’s original apple trees.

Visit the oldest church in Vermont and the adjacent Old First Church Cemetery which includes the gravesite of Robert Frost and other historic luminaries. Spend a few hours re-living history, wandering around Old Bennington, enjoying the beautiful revolutionary-era homes and scenic mountain views. 

Visit this meticulously preserved 35-room historic Victorian mansion in bucolic North Bennington. It’s set on 200 beautiful acres of grounds which include adjacent formal gardens, a working farm, and the popular Mile-Around network of trails.  A beautifully restored carriage barn makes an idyllic Vermont wedding venue.

The gravesite of one of the most beloved American poets, Robert Frost, in the Old First Church Cemetery in Old Bennington, is a popular stop for out-of-town visitors. 

Experience the real Vermont. Learn about history, local lore, and fun facts. Featuring daily Revolutionary and Civil War Tours as well as a Southern Vermont Sampler Tour.

Tours originate in Manchester, Vermont. Advanced reservations required.

There are five covered bridges in Bennington County. Three of them are lined up in a row over the Walloomsac River between Bennington and North Bennington, making for an easy visit: the Silk Road Covered Bridge, the Paper Mill Village Bridge, and the Henry Covered Bridge. The other two, the Chiselville Bridge and the West Arlington Bridge are also not far—in nearby Arlington, Vermont.

VAE is a non-profit community arts organization with a mission to strengthen communities and neighborhoods through the arts. The VAE sponsors a number of events and exhibitions, as well as summer camps.

Photo Credit: TW Collins

Check out this ‘great little gem’ of a professional theatre, featuring amazing productions in an intimate performance space.

Photo Credit: Tucker Bair

Family estate of Robert Todd Lincoln, son of Abraham Lincoln. Self-guided tours. A fully restored Pullman car. Snowshoeing and cross country skiing with rentals available. Working farm and walking trails.

The American Museum of Fly Fishing maintains a program of changing exhibitions in its Leigh H. Perkins Gallery that highlights the fly-fishing artifacts of the famous and not-so-famous.

A famous summer resident theater on the Williams College Campus, featuring favorite productions and talented, big name actors.

Photo Credit: Rob Ross

This is where the Battle of Bennington actually took place. 10 miles from downtown Bennington.

A 1700’s gristmill turned state of the art recording studio and performance venue. This creative campus now a meeting place for established and emerging creatives to collaborate and develop Revolutionary ideas in the Arts and Humanities.