5.0
(2)
50
riders
15
rides
Gravel biking in Bennington County offers an extensive network of unpaved roads, providing diverse routes for various skill levels. The region is characterized by rolling hills, dense forested areas within the Green Mountain National Forest, and significant elevation changes. Many routes traverse farmlands and follow river valleys, offering varied terrain and scenic views.
Last updated: April 30, 2026
8
riders
72.8km
04:59
1,460m
1,460m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
riders
127km
08:53
2,560m
2,560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
77.4km
05:25
1,320m
1,320m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
17.1km
01:07
300m
300m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
25.1km
01:34
420m
420m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
16.3km
01:06
320m
320m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Bennington County

Gravel biking in Lye Brook Wilderness
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Hiking in Bennington County
Road Cycling Routes in Bennington County
Cycling in Bennington County
Running Trails in Bennington County
Lyons Pond can be seen glistening between the tall pine trees. Many years ago, ice from the pond was stored in ice houses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.
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Hapgood Pond is a 12-acre pond that is 12 feet deep at its deepest point. This pond is within a recreation area of the same name. The recreation area has a campground, restrooms, picnic tables, and a swimming beach.
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The Bennington Battle Monument, erected in 1891, commemorates the Revolutionary War's Battle of Bennington in Vermont. Standing at 306 feet, it symbolizes the victory against British forces. Funded by patriotic citizens, the monument is a testament to the community's dedication to preserving and honoring its historical legacy.
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Established in 1762, The First Congregational Church of Bennington, or Old First Church, boasts a rich history in Old Bennington, Vermont. The present meeting house, erected in 1805, stands as a stellar representation of Federal period religious architecture in the state. Recognized for its historical significance, it earned a spot on the National Register of Historic Places in 1973.
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The Church of the Sacred Heart and St. Francis de Sales, located in Bennington, Vermont, holds a rich history dating back to its establishment. Serving as a spiritual cornerstone, the church's architectural and cultural significance draws interest. It stands as a testament to the community's enduring faith and heritage.
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The Mill Pond is a small pond off of the scenic West River in Londonderry, Vermont. It is just east of downtown Londonderry where you can get a bite to eat on your ride.
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Lyons Pond can be seen glistening between the tall pines trees. Many years ago, ice from the pond was stored in icehouses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.
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Bennington County offers a diverse range of gravel terrain. You'll find extensive networks of unpaved roads, from smoother gravel to more rugged "Class 4" roads that can feature rocks, mud, and roots. Many routes wind through picturesque farmlands, dense forested areas within the Green Mountain National Forest, and along river valleys, often involving significant elevation changes and challenging climbs. Wide tires (2 inches or wider) are often recommended for the more adventurous sections.
There are 14 gravel bike trails documented in Bennington County, offering a variety of experiences. These include 4 moderate routes and 10 more difficult options, ensuring there's something for different skill levels.
While many routes in Bennington County feature significant elevation and challenging terrain, there are moderate options that could be suitable for families with some biking experience. For example, the Gravel loop from Stratton Mountain is a moderate 25.1 km route, and the Weston Old Mill Museum loop from Weston is a moderate 16.3 km path, offering shorter distances and less extreme climbs.
Bennington County's gravel routes often lead through stunning natural landscapes. You can expect panoramic views of surrounding valleys and mountains from areas like Mount Anthony and Harmon Hill. Many trails follow natural watercourses, offering scenic sections alongside babbling brooks and through river valleys. Keep an eye out for serene bodies of water such as Equinox Pond, and don't miss the chance to visit Lookout Rock or the Mount Equinox and St. Bruno Scenic Viewing Center for breathtaking vistas.
Yes, Bennington County is rich in history. The Bennington Battle Monument – Bennington Battle Monument loop from Bennington is a great option, leading through historic areas and offering views of the iconic Bennington Battle Monument. You might also encounter historic covered bridges, like the Chiselville Covered Bridge, which add unique character to a ride and offer a glimpse into Vermont's past.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the extensive network of unpaved roads, the diverse terrain that caters to various skill levels, and the stunning natural beauty, particularly the forested landscapes and mountain views. The sense of exploration and discovery on less-maintained roads is also frequently highlighted.
Many of the gravel routes in Bennington County are designed as loops, offering convenient starting and ending points. Examples include the challenging Townshend Reservoir loop from Stratton Mountain and the moderate Gravel loop from Greendale Campground, allowing you to experience the region's beauty without retracing your path.
Bennington County offers seasonal beauty, making it a year-round outdoor destination. Spring brings wildflowers, summer offers lush greenery, and fall is spectacular with vibrant foliage. However, be aware that "Class 4" roads can be muddy, especially after rain or during spring thaw. Always check local conditions, as winter can bring snow, transforming the landscape into a wonderland but requiring different gear and considerations.
While not directly on a gravel bike route, the Lye Brook Falls Trail is a notable natural attraction in the region. It's a popular hiking trail known for its impressive waterfall, and could be a great addition to a day out in Bennington County, perhaps combined with a gravel ride nearby.
For experienced gravel bikers seeking a challenge, Bennington County has several difficult routes. The Weston Old Mill Museum – Morgan Hill loop from Hapgood Pond is a demanding 77.5 km trail with significant elevation changes. Another difficult option is the Townshend Reservoir loop from Stratton Mountain, a 72.8 km path exploring the area around Stratton Mountain.
Yes, Bennington County's network of roads allows for connections to various points of interest. Routes like the Townshend Reservoir loop from Stratton Mountain and the Gravel loop from Stratton Mountain specifically start from or explore the area around Stratton Mountain, offering opportunities to combine your ride with other activities or explore different parts of the region.


Check out more Gravel rides throughout Bennington County below and find the perfect route in your destination.
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