9 Best Sights in Bennington, Southern Vermont

The rich collections here feature military artifacts, early tools, dolls, and the Bennington Flag, one of the oldest of the Stars and Stripes in existence. Other areas of interest include early Bennington pottery, the Gilded Age in Vermont, mid-20th-century modernist painters who worked in or near Bennington, glass and metalwork by Lewis Comfort Tiffany, and photography, watercolors, and other works on paper. The highlight for many visitors, though, is the largest public collection of works by Grandma Moses (1860–1961), the popular self-taught artist who lived and painted in the area.

This 306-foot stone obelisk with an elevator to the top commemorates General John Stark's Revolutionary War victory over the British, who attempted to capture Bennington's stockpile of supplies. Inside the monument you can learn all about the battle, which took place near Walloomsac Heights in New York State on August 16, 1777, and helped bring about the surrender of British commander "Gentleman Johnny" Burgoyne two months later. The top of the tower affords commanding views of the Massachusetts Berkshires, the New York Adirondacks, and the Vermont Green Mountains.

Contemporary stone sculpture and white-frame neo-Colonial dorms surrounded by acres of cornfields punctuate the green meadows of the placid campus of Bennington College.

You'll find a swimming beach, nature trails, boat and canoe rentals, and a snack bar at this pretty park.

West of downtown, this National Register Historic District is well endowed with stately Colonial and Victorian mansions. The site of the Catamount Tavern, where Ethan Allen organized the Green Mountain Boys to capture Ft. Ticonderoga in 1775, is marked by a bronze statue of Vermont's indigenous mountain lion, now extinct.

The architecturally significant Park-McCullough House is a 35-room classic French Empire–style mansion, built in 1865 and furnished with period pieces. Several restored flower gardens grace the landscaped grounds, and a barn holds some antique carriages. Guided tours happen on the hour while the house is open. The grounds are open daily year-round.

Robert Frost came to Shaftsbury in 1920, he wrote, "to plant a new Garden of Eden with a thousand apple trees of some unforbidden variety." The museum, now part of Bennington College, tells the story of the poet's life and highlights the nine years (1920–29) he spent living in the house with his wife and four children. It was here that he penned "Stopping by Woods on a Snowy Evening" and published two books of poetry. You can wander 7 of the Frost family's original 80 acres. Among the apple boughs you just might find inspiration of your own.

In the graveyard of this church, the tombstone of the poet Robert Frost proclaims, "I had a lover's quarrel with the world."

At 2,400 feet, this has the highest state campground in Vermont. Adams Reservoir is the dominant feature and focus of activities, with swimming, fishing, and boating, including canoes, kayaks, and paddleboards for rent. A nature trail also circles the reservoir.