Bennington, Vermont: The Best Things to Do in This idyllic New England Town

By jhenr | Updated July 21st, 2022

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Bennington, Vermont, is one of the prettiest New England towns in the region, with its quaint downtown area and 19th-century buildings lining the streets. It’s also home to some of the best things to do in this New England town. So if you’re planning a trip to Bennington or already live here, these activities will give you an idea of just how much fun you can have in the area. Start exploring the possibilities!

Bennington Battle Monument

Aerial view of Bennington Vermont

Bennington Battle Monument is a historic site that commemorates the 1777 battle that took place near the town. It is located on top of a hill, and visitors can walk up a winding pathway to reach it. The monument is large and imposing, featuring three statues representing the fallen British forces, their commander General John Burgoyne and an American soldier who was slain during the fight. There are also two cannons nearby that have been cast from guns captured at Yorktown during the Revolutionary War.

Bennington Battle Monument

15 Monument Cir, Bennington, VT 05201-2134

Bennington Museum

Bennington, Vermont, USA – October 3, 2021: The front of the Bennington Museum in Vermont

Located in the heart of Bennington, the Bennington Museum is one of the best things to do in town. The museum houses a collection of over 60,000 objects, including paintings, sculptures, and pottery. There are also rotating exhibitions that showcase different aspects of Vermont’s history and culture. The museum is a great place to learn about the state’s rich history and culture.

Bennington Museum

75 Main St, Bennington, VT 05201-2885

Molly Stark Trail

Cycling woman and man riding on bikes at sunset mountains forest landscape. Couple cycling MTB enduro flow trail track. Outdoor sport activity.

The Molly Stark Trail is a 22.4-mile loop that takes you through some of the most beautiful scenery in Bennington. The trail is named after Molly Stark, who was the wife of General John Stark, and it offers stunning views of the Green Mountains, Taconic Mountains, and the Hoosac Range. There are also several historical sites along the way, making it a great option for history buffs.

Silk Road Covered Bridge

One of the best things to do in Bennington is visit the Silk Road Covered Bridge. This bridge was built in 1852 and spans 220 feet. It’s one of the only remaining covered bridges in Vermont and is a beautiful example of early American engineering.

Park–McCullough Historic House

Located in Bennington, Vermont, the Park–McCullough Historic House is a beautiful example of Second Empire architecture. The house was built in 1865 by Trenor Park, and it remained in the Park family until it was donated to the Bennington Museum in 1961. Today, visitors can tour the house and learn about its history. The Park–McCullough Historic House is one of the coolest things to do in Bennington, Vermont.

Oldcastle Theatre Company

People applauding in the movie theater. Standing ovation.

For more than 50 years, the Old castle Theatre Company has been a Bennington staple, producing professional live theatre. In addition to their regular season, they also offer educational opportunities and summer programming. If you’re looking for a night of entertainment, Old castle is a perfect choice.

Paper Mill Village Bridge

Bennington, Vermont – October 1st, 2019: Sign overlooking Papermill Village Bridge on a cold, Fall day in the New England town of Bennington

Bennington’s Paper Mill Village Bridge is one of the town’s most iconic landmarks. The bridge spans the Walloomsac River and is a popular spot for fishing, picnicking, and simply taking in the scenic views. Be sure to snap a photo of this beautiful bridge during your visit to Bennington!

Dollhouse and Toy Museum of Vermont

SHELBURNE, VT, USA – AUGUST 27, 2017: Vintage dolls on display in low lighting, in Shelburne, Vermont off of Shelburne Road. Editorial use only.

If you’re looking for a unique activity, check out the Dollhouse and Toy Museum of Vermont. This hidden gem is perfect for a rainy day and houses an impressive collection of dolls and toys. You can even purchase a dollhouse or toy to take home with you!


Bennington is the perfect place to enjoy all that Vermont has to offer. From its picturesque scenery and charming small-town feel, to its great outdoors and abundance of activities, there’s something for everyone in Bennington. So whether you’re looking for a relaxing getaway or an action-packed vacation, be sure to add this gem of a town to your list!