Cultural Attractions

Things To Do Cultural Attractions

Steeped in history. Rich in culture. Bennington’s mark on American history dates back to The Battle of Bennington, a turning point in the American Revolutionary War.

With roots in such acclaimed artists as Grandma Moses, Robert Frost, Norman Rockwell, Shirley Jackson and a modern-day enclave of arts and theatre, it is no wonder that Bennington ranks as a top tier most vibrant arts community in the nation year upon year.

A quintessential New England town — with world class museums, classic covered bridges, and classic Vermont Inns, Bennington Vermont has all of the makings of a perfect Vermont vacation.

Cultural Attractions

Bennington Battle Monument

15 Monument Circle,
Old Bennington, Vermont


2024 Opening: May 24th

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.


Bennington Museum

75 Main Street,
Bennington, Vermont


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.

The Dollhouse and Toy Museum of Vermont

212 Union Street
Bennington, 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.

Hemmings Motor News Car Lover’s Oasis (temporarily closed)

216 West Main Street
Bennington, Vermont

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!

Robert Frost Stone House Museum

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.

Old First Church

Rte 9 and Monument Avenue,
Old Bennington, Vermont


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. 

Park McCullough Historic Governor’s Mansion

1 Park Street
North Bennington, VT


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.

robert frost grave top bennington cultural attraction directional sign

Robert Frost Grave

Old First Church Cemetery
Rte 9 and Monument Avenue,
Old Bennington, Vermont 05201

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. 

Tours: Back Road Discovery

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.

Vermont Covered Bridges

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.

Vermont Arts Exchange (VAE)

48 Main St.
North Bennington, VT 05257


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

Bennington Theater (Formerly Oldcastle Theatre Company)

331 Main Street
Bennington, Vermont 05201


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

Monument Arts & Cultural Center

44 Gypsy Lane
Bennington, VT 05201


From the website: It all began with a dream to bring the arts to the Bennington community. The Monument Arts & Cultural Center is a unique and inviting home for theater, concerts, artist exhibits, outdoor music, workshops, dance classes, art classes, and so much more. Join us on this journey to reopen and establish the center as the heart of the Bennington community arts scene.

Bennington Cinemas

125 Phyllis Lane
Bennington, VT 05201


Fabulous 7-screen local cinema featuring the latest Hollywood releases.

Nearby Friends

And, here’s a nod to some of our Nearby Friends. Bennington’s convenient central location makes it an ideal launch pad for exploring popular attractions in nearby towns just a short drive away.

Clark Art Institute

225 South Street
Williamstown, Massachusetts


Photo Credit: Tucker Bair

Hildene, The Lincoln Family Home

1005 Hildene Road
Manchester, Vermont


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.


87 Marshall Street
North Adams, Massachusetts 01247


Museum of Fly Fishing

Route 7A South
Manchester, Vermont


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.

Williamstown Theatre Festival

1000 Main Street
Williamstown, MA 01267


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

Photo Credit: Rob Ross

Bennington Battlefield

Hoosick Falls, NY 12090


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

Southern Vermont Arts Center

West Road
Manchester, Vermont


The Mill Recording Studio and Creative Campus

316 Old Mill Road
East Arlington, Vermont 05252

(802) 430-7398

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.

Request to have your Bennington-based cultural attraction added or updated. Nearby cultural attractions within a 45-minute drive of Bennington will also be considered for inclusion.


Plan your visit.