Best things to do

Bennington Vermont

Whether you’re looking for a girlfriend getaway, a romantic weekend for two, or a family vacation, there is so much to do in Bennington VT.

Take a Self-Guided Walking Tour of Old Bennington

This historic village is home to less than 200 people, along with beautiful historic buildings, and a most colorful past. 

Eat Breakfast at a Historic Diner

Bennington is home to some fantastic eateries, but one of the most unique is the historic Blue Benn Diner on North Street.

Tour Bennington’s Beautiful Covered Bridge

Bennington County is fortunate enough to have five historic covered bridges, and they can all be explored in a single afternoon. 

Go Antiquing

Many of the antique stores in Bennington are located right on Main Street making it easy to search for the one-of-a-kind prize you never knew you needed.

Visit Bennington Museum

Bennington Museum is best known for housing the largest collection of Grandma Moses paintings in the world.

Check out the Bennington Battle Monument

At 306 feet, the Bennington Monument is the tallest building in the state, and it’s the most popular of all Vermont state historic sites.

Visit the Former Home and Grave of Robert Frost

Frost lived in the area from 1920 to 1929, and is buried behind the Old First Church in Bennington.

Hike a Section of the Appalachian/Long Trail

Vermont’s Long Trail was the first long-distance hiking trail in the United States and the inspiration for the much longer Appalachian Trail.

Drink Up at a Local Brewery or Distillery

- Harvest Brewing - Madison Brewing - Farm Road Brewing - Village Garage Distillery

Tour Park McCullough House in North Bennington

This historic, Victorian-era house was built in 1864 and is considered one of the finest and best-preserved Victorian mansions in New England.

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