Bennington’s Best Is Found In The Details (Here’s Where To Look)

Some towns leave an impression without trying too hard. Bennington has that way about it—slow corners, warm porches, and spots that feel like they’ve always been waiting. One visit leads to another, and soon, the map’s full. Here’s a list of stops that carry the town’s charm in small, everyday ways.

Climb The Bennington Battle Monument For Panoramic Views

The Bennington Battle Monument marks a turning point in the Revolutionary War—the 1777 battle it commemorates helped secure American independence. At 306 feet, it’s the tallest man-made structure in Vermont. Visitors can reach the top by elevator for tri-state views. August reenactments and 40,000 annual tourists keep its legacy alive.

Explore The Bennington Museum’s Grandma Moses Collection

Stop by the Bennington Museum to explore the largest collection of Grandma Moses paintings in the country. Her vibrant scenes of rural Vermont are a highlight. Inside, you’ll also find 200 years of local artifacts. Afterward, walk the wildflower trail and browse Vermont-made gifts like quilts and maple syrup.

Stroll Through Old First Church And Robert Frost’s Gravesite

Ever wondered what it’s like to visit a church that feels like a page from American history and poetry? Vermont’s oldest Protestant church, built in 1805, stands with its white steeple year-round. Nearby is Robert Frost’s grave, where hikers leave poems or small keepsakes. The church hosts candlelit Christmas services.

Visit Bennington Potters For Handcrafted Pottery

Bennington Potters has been crafting handmade pottery since 1948, keeping the tradition alive through skilled artisans who shape each piece with care—no two are exactly alike. Visitors are invited to watch the pottery-making process and shop the collection. Even celebrities like Martha Stewart have taken home their unique pieces.

Tour The Park-McCullough Historic Governor’s Mansion

Step into a 35-room mansion where history comes alive in every chandelier and velvet drape. The Park-McCullough estate, which once welcomed President Harrison, was constructed in 1865. Escape to its peaceful “secret garden” and enjoy arts events in the carriage barn. These stunning grounds celebrate timeless artistry and culture.

Photograph Bennington’s Five Covered Bridges

Love old bridges and pretty drives? Bennington has five 19th-century covered bridges, all packed into a scenic loop. Three of them cross the Walloomsac River, and each one, especially Silk Road and Henry, is a photo favorite. Locals also host bridge festivals with food and music. So, bring your camera to capture some true Vermont charm.

Dine At The Blue Benn Diner, A Retro Classic

Some places just feel like home, and the Blue Benn Diner is one of them. Since 1948, it has brought people together with comfort food and classic jukebox tunes. The menu offers everything from traditional turkey dinners to plant-based scrambles. Locals love it, and food guides often praise its welcoming charm.

Walk The Downtown Bennington Historic District

Few places showcase Vermont’s small-town history like Bennington’s Historic District. Rows of brick buildings evoke another time, and the occasional iron hitching post still remains. Independent businesses and public art have kept the area lively, offering visitors a glimpse of the past alongside today’s creative spirit.

Visit The Hemmings Motor News Car Lover’s Showcase

If you love cars, Hemmings Motor News in Bennington is a must-visit. You’ll find beautifully restored vehicles from the 1920s through the 1970s, along with a retro 1930s gas station. Every year, their classic car show attracts thousands of fans, and some visitors even get the chance to test-drive vintage cars.

Bike The Bennington Area Trail System (BATS)

The Bennington Area Trail System spans over 20 miles, connecting forests, rivers, and historic mill ruins. Designed with gentle slopes, the trails suit both bikers and hikers of all levels. Trail maps are available at local outfitters, and nearby shops offer bike rentals. Riders can cool off in the Walloomsac River.

Taste Maple Syrup At The Southern Vermont Maple Open House

Bennington’s Southern Vermont Maple Open House fills spring with the scent of fresh syrup. Explore sugarhouses, watch traditional tapping, and sample local treats like maple coffee and barbecue sauce. Pancake breakfasts are a big draw, so arriving early is key for a warm plate and a sweet start to the day.

Wander The North Bennington Outdoor Sculpture Show

Who says art belongs only inside museums? Each summer, North Bennington turns parks into outdoor galleries with contemporary sculptures on lawns and sidewalks. Some sculptures are interactive and invite you to touch or climb. Artists from around the world take part, bringing new pieces every year to keep the experience fresh and exciting.

Shop And Dine Along Main Street’s Local Boutiques

Main Street shows off small-town charm with historic buildings and shops full of local goods, from hand-thrown pottery to regional books. Grab a maple latte or a fresh salad made nearby. The welcoming atmosphere and strong community spirit draw visitors in, especially during fun events like the lively “Midnight Madness.”

Hike Mount Anthony For Sweeping Views

Locals call it “Bennington’s backyard” for a reason; Mount Anthony is that close and that stunning. The 4-mile round-trip trail is a manageable climb, and the reward is panoramic views that stretch across the valley. In fall, it becomes one of Vermont’s best leaf-peeping spots.

Enjoy A Performance At The Bennington Performing Arts Center

Looking for a night out in Bennington? Catch a show at the Performing Arts Center downtown. With just 120 seats, the theater keeps things cozy, whether it’s a musical or a concert. Broadway vets and touring acts sometimes pop in. Plus, student ticket prices and local art in the lobby make it extra charming.