4.7
(23)
1,036
riders
15
rides
No traffic road cycling routes in Bennington County traverse a landscape shaped by the Taconic Mountains to the west and the Green Mountains to the east, offering varied terrain. The region features river valleys, including the Walloomsac and Batten Kill, which provide scenic routes along their banks. Road cyclists encounter a mix of rolling roads and challenging climbs, with significant elevation changes in mountainous areas. The natural environment includes forested hillsides and open valleys, providing diverse backdrops for cycling.
Last updated: April 25, 2026
50
riders
110km
05:49
1,200m
1,200m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
33
riders
39.1km
02:19
910m
910m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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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.
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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Traffic-free bike rides in Bennington County

Traffic-free bike rides in Bennington County
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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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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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 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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Mount Greylock is the tallest peak in Massachussets. On a clear day, you can see up to 90 miles in the distance. At the peak, there is a visitor center, restrooms and a scenic viewing area.
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This old village is register as a US Historic site. It has well-preserved mid-19th century houses.
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There are 15 dedicated no traffic road cycling routes in Bennington County featured in this guide. These routes offer a range of difficulties, with 5 easy, 7 moderate, and 3 difficult options to explore.
Bennington County offers diverse terrain for road cyclists. You'll find routes nestled between the Taconic Mountains and the Green Mountains, providing both challenging climbs and scenic rolling roads. Many routes follow picturesque river valleys like the Walloomsac and Batten Kill, offering a mix of elevation and flatter sections.
Yes, Bennington County has options suitable for families. While this guide focuses on road cycling, the region offers dedicated pathways like the Bennington Rail Trail, which is accessible and great for gentler rides. Look for routes categorized as 'easy' in this guide for less challenging road cycling experiences.
Many routes offer stunning views and pass by notable landmarks. You might encounter picturesque spots like Equinox Pond or enjoy panoramic vistas from Lookout Rock. The historic Chiselville Covered Bridge is also a charming sight along several routes, such as the Chiselville Covered Bridge loop from Manchester.
The komoot community highly rates the no traffic road cycling in Bennington County, with an average score of 4.4 out of 5 stars. Cyclists often praise the stunning fall foliage, the peacefulness of the low-traffic roads, and the diverse landscapes ranging from mountain views to serene river valleys.
Absolutely! Bennington County is known for its charming covered bridges. You can cycle across the historic Chiselville Covered Bridge on routes like the Chiselville Covered Bridge – Chiselville Covered Bridge loop from Arlington, adding a unique historical element to your ride.
Yes, Bennington County offers challenging routes for experienced cyclists. For example, the Scotch Hill – Dead Lake loop from Emmaus House covers over 100 km with more than 1200 meters of elevation gain. Another demanding option is the Mount Greylock loop from The Clark Art Institute, featuring over 900 meters of climbing.
The fall season is particularly renowned for road cycling in Bennington County due to the spectacular fall foliage, transforming the landscape into vibrant colors. Spring and summer also offer excellent conditions with pleasant temperatures and lush greenery, though summer can be warmer.
Yes, many of the no traffic road cycling routes in Bennington County are designed as loops, allowing you to start and end at the same point. Examples include the Chiselville Covered Bridge loop from Manchester and The Mill Pond – Hapgood Pond loop from Peru.
Yes, Bennington County is dotted with serene lakes and river valleys. Some routes may offer views of or pass near lakes like Equinox Pond, or follow the scenic Walloomsac and Batten Kill rivers, providing beautiful waterside cycling experiences.
The routes in this guide cater to various skill levels. You'll find 5 easy routes perfect for a relaxed ride, 7 moderate routes offering a good balance of challenge and enjoyment, and 3 difficult routes for those seeking a more strenuous workout with significant climbs.


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