5.0
(4)
135
riders
16
rides
No traffic touring cycling routes in Bennington County are characterized by a diverse landscape, nestled between the Green Mountains and the Taconic Mountains. This region features varied terrain, including challenging climbs, rolling roads, and extensive wooded areas. Cyclists can experience scenic views of valleys and major rivers such as the Walloomsac and Battenkill, with routes often featuring significant elevation gain.
Last updated: April 25, 2026
10.6km
01:53
960m
190m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
26
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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14
riders
61.7km
04:19
1,080m
1,080m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
riders
84.9km
06:12
1,810m
1,810m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Traffic-free bike rides in Bennington County

Traffic-free bike rides in Bennington County
A great monument with a magnificent view once you have conquered the stairs. Tip: hike to the summit!
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Located just north of Adams, the Ashuwillticook Rail Trail Head sets a lovely tone for the rest of your ride along the trail, perfectly smooth and easy to use for families.
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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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Fitch Overlook is located on Notch Road at an elevation of 2,850 feet, just below Mount Fitch itself, at Mount Greylock State Reservation. It is not a large overlook by any means, but it has great views out over towards Mount Prospect and Stony Ledge.
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The 1753 House stands as a faithful reproduction of a settler's home from 1753 in The Berkshires. Situated in Field Park at Williamstown's west end, it was built by volunteers in 1953 to commemorate the town's Bicentennial. Early settlers in the Hoosac Valley, including Williamstown and North Adams, were obligated by contract to construct a house of specific dimensions and clear a designated amount of land to secure their lot. You can see the house from the roadside.
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Here's the Trail Head of the Ashuwillticook Rail Trail. The trail is perfectly smooth and easy to use for families.
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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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Bennington County offers a diverse selection of touring cycling routes designed to minimize traffic exposure. There are currently 18 routes available, ranging from moderate to difficult, ensuring options for various skill levels.
The terrain in Bennington County is quite varied, nestled between the Green Mountains and the Taconic Mountains. You'll encounter a mix of challenging climbs, rolling roads, and extensive wooded areas. Some routes, like the Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Pownal, specifically feature gravel sections, while others follow paved roads through river valleys like the Walloomsac and Battenkill.
While many of the listed routes are moderate to difficult, Bennington County does offer areas with gentler terrain. The region's rail trails, such as sections of the Ashuwillticook Rail Trail, provide flatter, car-free surfaces that can be more suitable for families or beginners, though some sections may require hybrid or mountain bikes. For a dedicated touring route, consider options with less elevation gain, keeping in mind that the area is generally hilly.
The best seasons for touring cycling in Bennington County are typically spring, summer, and especially fall. The fall foliage in the Green Mountains is spectacular. While winter cycling is possible, many routes may be covered in snow or ice, and specific 'no traffic' routes might not be maintained for winter use. Always check local conditions before heading out.
Bennington County's mountainous landscape means you should generally expect significant elevation gain on touring cycling routes. For example, the The Clark Art Institute – 1753 House loop from Williamstown features over 1800 meters of ascent, making it a challenging ride. Even shorter routes like Equinox Mountain via Skyline Drive involve nearly 1000 meters of climbing over just 10 kilometers.
Bennington County is rich in natural beauty and historical sites. Along your rides, you might encounter highlights such as the serene Equinox Pond, offering peaceful views. You can also find scenic viewpoints like Lookout Rock or the summit of Mount Equinox and St. Bruno Scenic Viewing Center. Historic covered bridges, like the Chiselville Covered Bridge, are also iconic features of the region.
Yes, many of the touring cycling routes in Bennington County are designed as loops, allowing you to start and end at the same point. Examples include the challenging The Spoke bicycle shop – Fitch Overlook loop from Harriman-and-West Airport and the extensive Ashuwillticook Rail Trail Head – Adams Overlook loop from North Adams, which offers a long-distance experience.
Parking availability varies by route. Many routes, especially those starting from towns or state parks, will have designated parking areas. For routes that begin from specific points like 'Harriman-and-West Airport' or 'Pownal', you can often find parking nearby. It's always advisable to check the specific route details on komoot for suggested starting points and parking information.
The touring cycling routes in Bennington County are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the stunning scenic views, the challenging yet rewarding climbs through the Green and Taconic Mountains, and the opportunity to explore historic areas and natural attractions like covered bridges and serene lakes, all while enjoying the peace of low-traffic roads.
Yes, the region features beautiful natural attractions. The Lye Brook Falls Trail is a notable highlight in Bennington County, offering a scenic hike to a impressive waterfall. While it might require a short detour or hike from a cycling route, it's a popular natural feature worth exploring.


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