Best attractions and places to see in Bennington County, Vermont, are situated between the Green and Taconic Mountains, offering a mix of natural landscapes and historical sites. This region features a variety of trails, viewpoints, and cultural landmarks. Visitors can explore numerous outdoor activities and discover sites of historical significance. The area provides diverse opportunities for exploration.
Last updated: April 24, 2026
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Popular around Bennington County
The Appalachian Trail — America's most iconic long-distance hike
The Long Trail — America's oldest long-distance path
New England – vibrant cities, picturesque coastlines and wild mountain landscapes
Hiking in Bennington County
Road Cycling Routes in Bennington County
Cycling in Bennington County
Running Trails in Bennington County

Gravel biking in Bennington County
The Long Trail, the oldest long-distance hiking trail in the United States, begins at the Massachusetts–Vermont border near Williamstown, MA. This southern terminus is marked by a large wooden sign and lies at the junction where the Appalachian Trail (AT) continues and the Long Trail (LT) begins. The first 105 miles of the LT coincide with the AT before the two trails split at Maine Junction near Killington, VT. There are two primary approaches to reach the southern terminus: Via the Appalachian Trail from North Adams, MA: This route is approximately 3.8 miles and begins at Route 2 in North Adams, or via the Pine Cobble Trail from Williamstown, MA: This 3.3-mile trail starts at Pine Cobble Road in Williamstown and offers a scenic ascent to the LT's starting point. Both approaches take hikers to the VT/MA border, where the Long Trail officially begins its 272-mile journey northward through Vermont's Green Mountains to the Canadian border.
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Equinox Mountain is a 3,855-foot summit that offers expansive views of the surrounding area. Skyline Drive tops out at the summit of the mountain along with a singletrack hiking trail.
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Equinox Pond is a small reservoir tucked in the trees in Green Mountains National Forest. The path around the pond is marked with white blazes and offers access to the edge of the water.
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Lookout Mountain offers a pretty sweet view down onto Manchester. The short spur trail leading to the summit has some good views itself.
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This is a stunning covered bridge. It is also known as the East Arlington Covered Bridge. It was built in 1870 and spans over the Roaring Branch of the Batten Kill on Sunderland Hill Road in the town of Sunderland, Vermont. There is a sign on the bridge that states you will get fined $1 if you drive over the bridge faster than a walking man.
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The Silk Covered Bridge, part of Silk Road, spans the Walloomsac River connecting Bennington and North Bennington, Vermont. Constructed in 1840, this Town lattice truss bridge is one of three in the vicinity. Its historical significance led to its inclusion in the National Register of Historic Places in 1973.
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This is a stunning covered bridge. It is also known as the East Arlington Covered Bridge. It was built in 1870 and spans over the Roaring Branch of the Batten Kill on Sunderland Hill Road in the town of Sunderland, Vermont. There is a sign on the bridge that states you will get fined $1 if you drive over the bridge faster than a walking man.
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Heads up: Although this trail and its ultimate destination are both beautiful, you'll often have to cross washouts and non-bridged streams along the way. Wet feet may ensue. If you don't want to pack a second set of footwear for possible water crossings, you should at least wear non-cotton socks to help reduce chafing and cold feet.
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Bennington County is nestled between the Green and Taconic Mountains, offering diverse natural landscapes. You can visit Equinox Pond, a small reservoir in the Green Mountains National Forest, or explore Woodford State Park and Lake Shaftsbury State Park for serene lake experiences. The Walloomsac River is known for fly fishing, and sections of the Appalachian and Long Trails offer extensive hiking opportunities.
Yes, the region is rich in history. The Bennington Battle Monument commemorates a pivotal Revolutionary War victory and offers panoramic views from its observation deck. The Old First Church, completed in 1805, is an architectural gem with a historic cemetery where poet Robert Frost is buried. You can also explore the Park-McCullough Historic Governor's Mansion or visit several historic covered bridges like the Chiselville Covered Bridge and Silk Covered Bridge.
For expansive views, head to Lookout Rock, which offers a great perspective over Manchester. Another excellent spot is Mount Equinox and St. Bruno Scenic Viewing Center, accessible via Skyline Drive, providing broad vistas of the surrounding area. The Bennington Battle Monument also features an observation deck with views spanning Vermont, New York, and Massachusetts.
Many attractions are suitable for families. Equinox Pond is a great spot for a leisurely walk around the water. The Chiselville Covered Bridge and Silk Covered Bridge are picturesque and easy to visit. Woodford State Park and Lake Shaftsbury State Park offer swimming, kayaking, and nature trails. The Mile-Around Woods, connected to the Park-McCullough Historic Governor's Mansion, provides easy walking trails.
The Bennington Museum houses a comprehensive collection of regional art and history, including the world's largest collection of Grandma Moses paintings. The Robert Frost Stone House Museum in Shaftsbury is where the poet wrote many famous works. The Old First Church, beyond its historical significance, is a cultural landmark due to its cemetery being the final resting place of Robert Frost. The Monument Arts & Cultural Center also hosts various events and exhibits.
Yes, Bennington County offers numerous hiking opportunities. You can explore the Lye Brook Falls Trail, which leads to a beautiful waterfall, or hike to Harmon Hill for scenic views. For more options, check out the guide to Easy hikes in Bennington County, which includes trails like The Mile-Around Woods and Branch Pond Trail.
Beyond hiking, Bennington County provides opportunities for running and road cycling. You can find various running routes, including loops around Equinox Mountain or Mill Pond, detailed in the Running Trails in Bennington County guide. For cyclists, there are road cycling routes that pass by scenic spots like the Chiselville Covered Bridge, as highlighted in the Road Cycling Routes in Bennington County guide.
Bennington County is beautiful year-round, but it is especially renowned for its vibrant fall foliage. The region transforms into a picturesque display of reds, oranges, and yellows, making autumn a very popular time to visit. Summer offers pleasant weather for outdoor activities, while spring brings blooming landscapes. Winter provides opportunities for snow sports, though some attractions may have reduced hours.
Beyond the main attractions, consider visiting the Blue Benn Diner, a classic rail car diner operating since 1948, for a nostalgic dining experience. Exploring the various historical societies in towns like Shaftsbury, Readsboro, and Dorset can offer deeper insights into local history. The Robert Frost Trail, a two-mile nature trail starting behind the Robert Frost Stone House Museum, is also a peaceful and less-trafficked option.
Visitors frequently praise the stunning views from spots like Lookout Rock and Mount Equinox. The peaceful atmosphere of places like Equinox Pond and the beauty of the covered bridges, such as the Chiselville Covered Bridge, are also highly appreciated. Many enjoy the blend of natural beauty with significant historical sites throughout the region.
Yes, Bennington County is home to sections of both the Appalachian and Long Trails. The Long Trail Southern Terminus is located in the region, offering access to this famous long-distance footpath. These trails provide opportunities for challenging day hikes or multi-day backpacking adventures through the Green Mountains.


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