Bennington is often called “the gateway to Vermont,” and with its southwestern-corner proximity to Massachusetts and New York, the moniker makes sense. The town’s Revolutionary War history is still on display, right alongside a vibrant arts scene, thanks in part to offbeat Bennington College. On Main Street, family-owned shops and restaurants are a buzzing backdrop for annual events such as the Mayfest Arts & Crafts Festival and Labor Day weekend’s Garlic Town USA — billed as “a stinkin’ good time.”

If you want to visit Bennington, Vermont, here’s a suggested itinerary.

Note: Check websites to confirm business hours for the day you visit.

The Bennington Battle Monument

A 306-foot-tall obelisk greets travelers as they head into Bennington. The monument was completed in 1891 to commemorate the 1777 Battle of Bennington — fought in defense of the town's food and military supplies — which resulted in a pivotal victory for colonial forces during the Revolutionary War. The tallest man-made building in Vermont, it draws thousands of visitors each May through October to its observation deck, from which viewers can see three states.
15 Monument Cir., Old Bennington

Blue Benn Diner

This 1948 Silk City diner car feels unchanged by time — or by its new owner. "If it ain't broke, don't fix it," said John Getchell, who frequented the diner as a Bennington College student in the early '80s and bought it in December 2020. Pop a quarter in the tabletop selector of the antique Seeburg Select-O-Matic jukebox, rest your elbows on the deeply worn counter and order a sugared cake doughnut. The Blue Benn has been a local staple for 76 years for a reason.
314 North St., Bennington

Bennington Museum

In a stone building that was once a church, Bennington Museum has the largest collection of art and historical artifacts in southern Vermont — more than 40,000 objects in its permanent collection — including Bennington pottery and the world's largest public collection of paintings by American folk artist Grandma Moses. Rotating exhibitions in its 13 gallery spaces have included major 20th-century modernists, including Rockwell Kent and Helen Frankenthaler; one-night-only tattoo art events; and student art shows. The museum’s goal is “to celebrate the creativity of Vermont in all its forms, from the 18th century to the present, and to inspire innovation in the future.”
75 Main St., Bennington

Taste the Craft

The Southern Vermont HomeBrew Festival hits Depot Street each May, with local DIY-ers bringing their best sips to sample. The rest of the year, Bennington’s pros offer artisanal ales and sumptuous spirits. Start at Madison Brewing (428 Main St.), a brewpub that’s been in biz since the early 1990s. Next, hit Harvest Brewing (201 South St.), a nanobrewery that also roasts its own coffee. Little City Cider (139 Shields Dr.) often pairs its appley pours with live music, and Village Garage Distillery (107 Depot St.) offers tastings and tours of its Vermont-sourced spirits.

Take a Hike

The country-spanning Appalachian Trail and Vermont’s Long Trail run concurrently in southern Vermont, but long-distance hikers need not have all the fun. From a parking area five miles east of town on Route 9, the trails wind through the Green Mountain National Forest. Head south — starting with a steep climb — to Harmon Hill for expansive views, or head north into the Glastenbury Wilderness, where local legend points to Bigfoot sightings and a ghost town’s spooky happenings.

Shop the Main Strip

Bennington’s downtown has a 60-year tradition of Midnight Madness — an annual after-dark shopping extravaganza in late July. But the shops bustle year-round, with everything from antiques to xylophones. Grab a treat at the Village Chocolate Shoppe (471 Main St.); a novel at Vermont’s oldest independent bookstore, the Bennington Bookshop (109 South St.); a new hobby at the Gamer’s Grotto (457 Main St.); a musical instrument, rock tumbler or Vermont souvenir at Knapps (417 Main St.); or a houseplant and a coffee at hip café-shop W. Collective (198 North St.).

Pay Your Respects to a Poet

It doesn’t need to be a snowy evening to stop by the grave of Robert Frost, located in the Bennington Centre Cemetery at the historic white-steepled Old First Church (60 Monument Ave., Old Bennington). A short drive away, Bennington College runs the Robert Frost Stone House Museum (121 Route 7A, Shaftsbury; open May-October and by appointment November-April), where the “bard of New England'' lived from 1920 to 1929. There, Frost wrote "Stopping by Woods on a Snowy Evening" — ironically on a hot June morning. From the museum, a two-mile trail winds through the woods to Lake Paran (Houghton St., North Bennington), which offers swimming and kayaking in summer and ice fishing and skating in winter.