The Best Things To Do In Bennington, Vermont

By Allison Tibaldi

A Victorian mansion in Bennington, VermontPhotographs in Carol M. Highsmith's America Project in the Carol M. Highsmith Archive, Library of Co

Bennington sits in a cozy corner of Southern Vermont. It was once the headquarters of the Green Mountain Boys, a militia who successfully resisted New York’s territorial claim and kept Vermont intact.

This spunky rebel spirit can be seen today in the vibrant downtown; urban redevelopment thrives with the help of a community that’s committed to frequenting Mom-and-Pop businesses. With very few chain stores and even fewer empty storefronts, Bennington bucks cookie-cutter trends and proudly embraces its independent steak. The Battle of Bennington was a tide-turning moment in the American Revolution, so there’s history here to accompany the crisp mountain air. Get ready for an all-season, car-free weekend getaway to Bennington.

What to Do in Bennington, Vermont

The Bennington Museum exemplifies the creative spirit that defines Vermont. Though modest in size, it is home to the largest public collection of works by Grandma Moses anywhere in the world. A visit offers the visual stimulation of her whimsical folk art paintings as well as a complementary Grandma Moses Schoolhouse exhibit. This re-creation of a 19th century one-room schoolhouse gives visitors a window into her life and explores how her experiences translated onto the canvas. Additional ongoing exhibits include an informative one on Vermont’s Gilded Age. There are temporary exhibits that rotate frequently so there’s often something fresh to view. The lovely George Aiken Wildflower Trail, adjacent to the museum, showcases native wildflowers and ferns.

Constructed in local limestone, the Bennington Battle Monument is Vermont’s most popular historic site. It was built to commemorate the 1777 Battle of Bennington, a significant turning point in the Revolutionary War. Head to the top of this 306-foot tower and get a tri-state view of New York, Massachusetts and Vermont. 

Hiking is a wonderful way to get in touch with Bennington’s fairytale landscapes. In winter, snowshoeing is a popular pastime. Southern Vermont College Hiking Trails present a range of active options just a few miles from downtown. Consider the two-mile Halloween Tree or the easy half-mile Carriage Road with lovely Green Mountain views.

Watch this video to get a glimpse into Bennington:

Shopping in Bennington

Bennington’s Main Street is home to an eclectic array of independently owned shops. Check out the vinyl at Knapp’s along with electric guitars, basses and ukuleles. 

At the Village Chocolate Shoppe, enjoy mouth-watering classic confections like butter crunch and fudge. Avalanche Bars, a combination of coconut, marshmallow and chewy caramel, are worth every calorie. 

The Bennington Bookshop is the oldest independent bookstore in Vermont. There’s a rich array of New England and Vermont authors as well as a large children’s section. 

The local arts and craft scene is robust. Set on three leafy acres in downtown, Bennington Potters has been making pottery in town for over seventy years. Purchase a classic mug designed by founder David Gil that is equal proportions functional, durable and beautiful. Platters, bowls, casseroles and pie plates are some of the many fine pieces for sale. Michelle Obama selected a blue agate pattern place setting for White House dining room. After you’ve shopped, head to the workshop and watch the pressing, casting, firing and glazing process in action. 

The Best Spot to Eat and Drink in Bennington

Madison Brewing Company is the place for craft beer paired with pub food. Try their popular Downtown IPA with a refreshing burst of citrus or the Sucker Pond Blonde, brewed with German Noble hops and house yeast. The meaty chili, topped with smoky local cheddar cheese, is a winner. Burgers and bratwurst are delicious and pair particularly well with a cold beer. 

Where to Stay 

Simply put, the Four Chimneys Inn is one of New England’s finest accommodations. Located just a few minutes walk from downtown, this charming oasis benefits from the personal touch of the dedicated owners and innkeeper. There are eleven guest rooms, several with wood-burning fireplaces, glass porches, hardwood floors and jetted bathtubs. Each feels private and elegant yet never ostentatious. The common area presents a blazing fireplace and a welcoming bar. A hearty morning meal is served to each guest, included in the room rate. You select your breakfast choice the night before and feast in the morning. 

Get to Bennington from New York City.

Ride Amtrak to Albany and catch the Vermont Shires Connector bus for a smooth journey to Bennington. 

Follow us to see more articles like this.

...

Follow