Bennington, Vermont, is a charming town with a wealth of activities and attractions. Whether you’re seeking outdoor adventures, cultural experiences, historic sites, or delightful eateries, Bennington has something for everyone. This guide will take you through the top things to do in Bennington, ensuring you make the most of your visit to this picturesque New England destination.
Explore Downtown Bennington
Stroll Through Main Street
Main Street in Bennington is the heart of the town, bustling with shops, cafes, and historic buildings. A leisurely stroll will allow you to take in the local culture, explore unique stores, and enjoy the friendly atmosphere.
Visit the Bennington Welcome Center
Start your journey at the Bennington Welcome Center. Here, you can gather maps, brochures, and valuable information about local attractions and events.
Discover Bennington’s Historic Sites
Bennington Battle Monument
Address: 15 Monument Circle, Bennington, VT
The Bennington Battle Monument, standing at 306 feet, is Vermont’s tallest structure. It commemorates the Battle of Bennington, a pivotal victory during the Revolutionary War. From May to October, visitors can take an elevator to the top for breathtaking views of Bennington and the surrounding Green Mountains.
Old First Church
Address: 1 Monument Circle, Bennington, VT
Built in 1805, the Old First Church is one of Vermont’s most beautiful and historic churches. It is located near the Bennington Battle Monument and is a key stop on the Old Bennington walking tour.
Robert Frost Stone House Museum
Address: 121 VT-7A, Shaftsbury, VT
Visit the former home of renowned poet Robert Frost. The museum showcases Frost’s life and work, and the surrounding trails offer a glimpse into the natural beauty that inspired his poetry.
Experience Outdoor Adventures
Hiking and Biking
Bennington is surrounded by the Taconics and Green Mountains, providing ample opportunities for hiking and biking. The Bennington Area Trail System (BATS) offers trails for all skill levels, including scenic routes with stunning views.
Lake Shaftsbury State Park
Address: 262 Lake Shaftsbury Rd, Shaftsbury, VT
Lake Shaftsbury State Park is perfect for hiking, swimming, kayaking, and picnicking. The park features a one-mile trail around the lake, a sandy beach, and boat rentals.
Woodford State Park
Address: 142 State Park Rd, Woodford, VT
Woodford State Park, located at 2,310 feet above sea level, offers hiking trails around Adams Reservoir, canoe and kayak rentals, and beautiful wooded areas for exploration.
Enjoy Unique Dining Experiences
Blue Benn Diner
Address: 318 North St, Bennington, VT
The Blue Benn Diner is a historic eatery known for its classic diner fare and eclectic choices. Open since 1948, it remains a beloved local institution with jukeboxes on every table and a warm, nostalgic atmosphere.
South Shire Inn and Niramet Thai Restaurant
Address: 124 Elm St, Bennington, VT
For an upscale dining experience, visit the South Shire Inn. This Victorian home houses a delightful Thai restaurant, Niramet, offering a blend of traditional and modern Thai cuisine.
Visit Local Breweries
Madison Brewing Company
Address: 428 Main St, Bennington, VT
Madison Brewing Company is a local favorite, serving up a variety of craft beers and delicious pub fare. It’s the perfect spot to relax after a day of exploring.
Harvest Brewing
Address: 201 South St, Bennington, VT
Harvest Brewing offers a cozy atmosphere and a rotating selection of craft beers. It’s a great place to sample local brews and enjoy live music events.
Tour Bennington’s Covered Bridges
Silk Road Covered Bridge
Another must-see is the Silk Road Covered Bridge, constructed in 1840. It’s a charming spot for photos and a peek into the past.
Paper Mill Village Bridge
This bridge, dating back to 1889, is located in the Paper Mill Village area and provides a scenic backdrop for a leisurely afternoon.
Shop for Antiques
Main Street Antiques
Address: 473 Main St, Bennington, VT
Main Street Antiques is a treasure trove of unique finds, from vintage furniture to rare collectibles. It’s a great place to hunt for one-of-a-kind souvenirs.
Monument Vintage
Address: 435 Main St, Bennington, VT
Just a short walk from Main Street Antiques, Monument Vintage offers an eclectic mix of antiques and curiosities. It’s a haven for collectors and enthusiasts.
Immerse Yourself in Art and History
Bennington Museum
Address: 75 Main St, Bennington, VT
The Bennington Museum is a cultural hub, featuring exhibits on local history, art, and the largest collection of Grandma Moses paintings. It also offers special events and an outdoor nature trail.
Park McCullough House
Address: 1 Park St, North Bennington, VT
The Park McCullough House is a beautifully preserved Victorian mansion from 1864. Visitors can tour the house, stroll the gardens, and explore the Mile-Around-Woods trail.
Hike and Explore Nature Trails
Appalachian Trail/Long Trail
The Appalachian Trail and Long Trail converge near Bennington, offering hikers the chance to experience sections of America’s oldest long-distance trail. Popular hikes include the route to Harmon Hill, which provides stunning vistas.
Mile-Around-Woods
Located near the Park McCullough House, the Mile-Around-Woods offers woodland and pasture trails with far-reaching mountain views. It’s a peaceful spot for a leisurely walk.
Bennington Area Trail System (BATS)
BATS features a network of multi-use trails on Mount Anthony. Hikers and mountain bikers can explore various routes, including a secret cave and an abandoned mansion.
Plan Your Visit
When to Go
Bennington is beautiful year-round, but the best time to visit is from May to October, when the weather is pleasant, and outdoor activities are in full swing.
Where to Stay
For a luxurious stay within walking distance of downtown, consider the South Shire Inn. This Victorian home offers nine delightful rooms and an on-site Thai restaurant, Niramet.
How to Get There
Bennington is conveniently located three and a half hours from New York City, three hours from Boston, and an hour from Albany, making it an accessible getaway from major metropolitan areas.
Conclusion
Bennington, Vermont, is a hidden gem that offers a perfect blend of outdoor adventures, historic sites, cultural experiences, and unique dining. Whether you’re planning a romantic weekend, a family vacation, or a solo retreat, Bennington promises a memorable and enriching experience. So pack your bags and get ready to explore all the fabulous things Bennington has to offer