5.0
(4)
135
riders
45
rides
Touring cycling in Bennington County offers diverse landscapes, from mountainous terrain to river valleys and extensive woodlands. The region is situated between the Green Mountains and the Taconic Mountains, providing a variety of elevations and scenic backdrops. Cyclists can find both paved and gravel roads that cater to different preferences and fitness levels. This area is characterized by its natural features and historical charm, making it suitable for varied touring cycling experiences.
Last updated: April 26, 2026
10.6km
01:53
960m
190m
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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5
riders
38.2km
02:23
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
3
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
72.7km
06:53
1,230m
1,230m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
22.9km
02:01
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
18.3km
01:39
260m
260m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
67.7km
05:37
960m
950m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
64.3km
03:59
630m
630m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Bennington County
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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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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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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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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Bennington County offers a wide selection of touring cycling routes, with over 40 distinct tours available. These routes cater to various preferences, including easy, moderate, and difficult options, ensuring there's something for every cyclist.
You can expect a diverse range of terrain, from mountainous landscapes and challenging climbs to picturesque river valleys and extensive woodlands. The region, nestled between the Green Mountains and the Taconic Mountains, features both paved and gravel roads, offering varied experiences for touring cyclists.
Yes, Bennington County features several excellent gravel touring routes. A notable option is the Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Pownal, which offers a challenging ride through scenic working farms and past the historic Bennington Battle Monument.
Absolutely. Bennington County is known for its mountainous terrain, providing plenty of challenging routes. For instance, the Equinox Mountain via Skyline Drive is a difficult route featuring a substantial climb with panoramic views. Many of the 28 difficult routes in the area offer significant elevation gains.
Many of the touring cycling routes in Bennington County are designed as loops, allowing you to start and end at the same point. An example is the Chiselville Covered Bridge loop from Lye Brook Falls Trailhead, which takes you through varied terrain and past historic covered bridges.
Bennington County offers stunning natural beauty. Along your rides, you can enjoy panoramic views from locations like Mount Anthony Road and Zaphod's Run. You might also encounter scenic rivers such as the Walloomsac and Battenkill, and tranquil lakes like Lake Paran and Lake Shaftsbury. For specific viewpoints, consider visiting Lookout Rock or the summit of Mount Equinox.
Yes, the region is rich in history. You can cycle past the iconic Bennington Battle Monument, commemorating a pivotal Revolutionary War battle. Additionally, routes like the Chiselville Covered Bridge loop allow you to experience historic covered bridges, such as the Chiselville Covered Bridge itself.
The best time for touring cycling in Bennington County is generally from late spring through fall. The fall foliage season is particularly vibrant, offering breathtaking views along routes like the Molly Stark Byway. Summer provides warm weather for exploring, while spring brings fresh greenery. Always check seasonal trail conditions before heading out.
Yes, Bennington County has options for all skill levels. While many routes are moderate to difficult, there are 3 easy touring cycling routes available. The Bennington Rail Trail, though not a touring route in this guide, is a paved and crushed stone path suitable for various activities including biking, and offers a gentler experience for families.
The touring cycling experience in Bennington County is highly regarded by the komoot community, with an average rating of 4.75 stars from over 5 reviews. Cyclists often praise the diverse landscapes, from challenging mountain climbs to serene river valleys, and the blend of paved and gravel options.
Parking is generally available at various trailheads and points of interest throughout Bennington County. For specific routes, it's advisable to check the route details on komoot for designated parking areas or nearby public parking facilities.
While many outdoor areas in Bennington County are dog-friendly, policies can vary by specific trail or park. For touring cycling routes, it's best to check individual route descriptions or local regulations regarding dogs, especially if you plan to bring your furry companion.
Bennington County's extensive network of routes and proximity to natural areas like Woodford State Park and the Green Mountain National Forest make it suitable for multi-day touring. Woodford State Park offers camping opportunities, allowing cyclists to combine longer rides with overnight stays in nature. You can plan your multi-day adventure by linking several routes together.


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