Things To Do In Bennington

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

A Stroll Down Main Street - Outside Our Bubble

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

Bennington Welcome Station | Shunpiking with Ray

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

Bennington Battle Monument to Undergo Multiyear Renovation | True 802 |  Seven Days | Vermont's Independent Voice

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

The Old First Church - Bennington, VT

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

Robert Frost Stone House Museum | Bennington College

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

Hiking & Mountain Biking in Nakusp | Halcyon Hot Springs

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

Lake Shaftsbury State Park | Outdoor Project

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

Woodford State Park - All You Need to Know BEFORE You Go (2024)

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

Photos | The 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

South Shire, Bennington – Updated 2024 Prices

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

Madison Brewing Co. Brew Pub & Restaurant - Picture of Madison Brewing Co.  Brew Pub & Restaurant, Bennington - Tripadvisor

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

Bennington Vermont Silk Covered Bridge by Adam Jewell

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

Paper Mill Village Covered Bridge - Vermont fine-art photography prints

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

Main Street Antique Mall | Michigan

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

Background Image of Washington Mounument from the Lincoln Memorial

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

Bennington Museum & The Grandma Moses Exhibits

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

Park-McCullough Historic Governor's Mansion | North Bennington, VT  Reception Venues - The Knot

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 Long Trail - Green Mountain Club

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.


Sunday Photo Essay: Mile-Around Woods - Vermont Begins Here

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)

Bennington Area Trail System (BATS) - Trail Finder

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

8 Amazingly Beautiful Places to Visit in Bennington, Vermont

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.


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