4.7
(23)
1,048
riders
50
rides
Road cycling in Bennington County offers diverse terrain, situated between the Green Mountains and the Taconic Mountains. The region features a mix of challenging climbs, rolling roads, and scenic river valleys, including those of the Walloomsac and Battenkill rivers. Extensive woodlands and pastoral landscapes characterize many routes, providing varied backdrops for rides. Cyclists can expect a combination of paved and gravel surfaces, often passing by historic landmarks and working farms.
Last updated: April 30, 2026
28
riders
37.2km
01:51
360m
360m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
21
riders
35.0km
01:34
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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15
riders
56.9km
02:57
620m
620m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
14
riders
73.6km
03:36
740m
740m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
13
riders
44.7km
02:34
590m
590m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
11
riders
53.3km
02:28
580m
580m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
14
riders
102km
06:09
1,110m
1,110m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
9
riders
47.9km
02:09
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
82.2km
03:53
1,100m
1,100m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
11
riders
38.0km
02:29
510m
510m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Bennington County
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Probably more impressive to ride/drive up through McCauley Road. You can also access it from Natural Bridge or Hudson Brook Lane Road on foot or on a bike (which is what we did). White marble natural bridges/quarries are apparently not very common in the North America. Worth the detour if you are in North Adams.
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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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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 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 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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The beautiful Hoosic River runs through three states and is fed by streams from the Green Mountains of Vermont, the Taconics of New York and the lofty sides of Mount Greylock, the highest peak in Massachusetts (3,491 ft.). Its meandering journey travels 70 miles from where it begins at the Cheshire Reservoir in Massachusetts, to where it eventually enters the Hudson River at Stillwater, NY.
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Bennington County offers a diverse range of terrain, situated between the Green Mountains and the Taconic Mountains. You'll find a mix of challenging climbs, rolling roads, and scenic river valleys. Routes often combine paved and gravel surfaces, passing through extensive woodlands and pastoral landscapes. Difficulty levels vary, with 8 easy routes, 29 moderate routes, and 14 difficult routes available.
Yes, Bennington County has several easy road cycling routes perfect for beginners. One such route is the Mill Pond – Trout Pond loop from Manchester, which is 19.7 miles (31.8 km) long and leads through woodlands and past serene ponds. There are 8 easy routes in total to explore.
For experienced riders seeking a challenge, Bennington County offers 14 difficult routes. A notable option is the Schoolhouse Lake – Schuylerville Yacht Basin loop from Red Mill on the Batten Kill. This route is 75.6 miles (121.7 km) long, features significant elevation gain, and traverses varied landscapes, typically taking over 6 hours to complete.
Road cycling routes in Bennington County are rich with natural beauty. You'll often ride through extensive woodlands, past serene bodies of water like Lake Paran and Lake Shaftsbury, and alongside river valleys such as the Walloomsac and Battenkill. The region is nestled between the Green Mountains and the Taconic Mountains, providing breathtaking views and diverse landscapes.
Yes, many road cycling routes in Bennington County incorporate charming historic landmarks. You can expect to pass by working farms and historic covered bridges, including the Chiselville, Silk Road, Paper Mill, and Burt Henry bridges. The Chiselville Covered Bridge loop from Manchester specifically highlights one of these iconic structures, the Chiselville Covered Bridge.
Bennington County offers numerous scenic viewpoints, thanks to its mountainous terrain and river valleys. Routes often provide sweeping valley views, especially in areas like the Mile-Around-Woods or trails within the Bennington Area Trail System (BATS) that access higher elevations. For a dedicated viewpoint, consider routes that pass near Lookout Rock or Mount Equinox and St. Bruno Scenic Viewing Center.
While specific 'family-friendly' designations for road cycling can vary, routes with less elevation gain and shorter distances are generally suitable. The Mill Pond – Trout Pond loop from Manchester is an easy 19.7-mile route that could be a good option for families. Additionally, the Bennington Area Trail System (BATS) offers multi-use trails like the Carriage Road, which are beginner-friendly and wind through historic areas.
Yes, many of the road cycling routes in Bennington County are designed as loops, offering convenient starting and ending points. Examples include the Schoolhouse Lake – Schuylerville Yacht Basin loop from Red Mill on the Batten Kill, the Chiselville Covered Bridge loop from Manchester, and the Silk Covered Bridge loop from North Bennington.
The best time for road cycling in Bennington County is generally from spring through fall. The region is particularly stunning in the fall when the extensive woodlands display vibrant foliage. Warmer months offer pleasant conditions for exploring the diverse terrain, but it's always advisable to check local weather forecasts before heading out.
While specific parking details for every route are not listed, many routes in Bennington County start from towns or recreational areas where parking is typically available. For example, the Chiselville Covered Bridge loop starts from Manchester, a town with various parking options. It's recommended to check the starting point of your chosen route for specific parking information.
The komoot community highly rates road cycling in Bennington County, with an average score of 4.5 stars from 4 reviews. Cyclists often praise the region's diverse terrain, the scenic beauty of its river valleys and woodlands, and the charm of historic covered bridges. The variety of routes, from easy loops to challenging climbs, is also a frequently appreciated aspect.
Yes, several road cycling routes in Bennington County will take you past beautiful lakes and ponds. For instance, the South Village Pond – Emerald Lake loop from Mettawee River and the South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead both feature serene bodies of water. The Hapgood Pond – Lyons Pond loop from Hapgood Pond Recreation Area is another great option.


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