5.0
(1)
55
riders
12
rides
Road cycling routes around Bennington, Vermont, traverse a varied landscape situated between the Green Mountains and the Taconic Mountains. The region features rolling hills, providing both sustained climbs and scenic descents. Routes often follow rivers like the Walloomsac and pass through woodlands, offering shaded sections and views of natural features. This topography creates diverse road cycling experiences for different skill levels.
Last updated: May 17, 2026
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.
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.

Sign up for free
4
riders
72.5km
03:10
580m
580m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4
riders
72.4km
03:30
1,010m
1,010m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
7
riders
55.6km
02:35
540m
540m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Bennington
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.
0
0
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.
0
0
Cycling on this good quality road next to Thurber Pond is a joy with the pond directly in view. Keep your eyes peeled for the various pond life and birds that live around it.
0
0
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.
0
0
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.
0
0
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.
0
0
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.
0
0
The Cold Spring Preserve borders the southern grounds of The Clark Art Institute, a well known local art museum with an impressive collection of 19th-century French Impressionist and Academic paintings and beautiful grounds. This is a nice place to slow down as you ride to admire the views and look out for wildlife.
0
0
Road cycling routes in Bennington, Vermont, offer a diverse terrain characterized by rolling hills and mountain views, situated between the Green Mountains and the Taconic Mountains. You'll find sustained climbs leading to panoramic vistas, as well as scenic descents. Many routes also meander through woodlands, providing shaded sections, and often follow rivers like the Walloomsac, offering tranquil scenery.
Yes, Bennington offers routes suitable for various skill levels, including easier options. While many routes feature rolling hills, there is at least one easy route available. For a generally flatter and accessible option, the Bennington Rail Trail caters to cyclists of all ages and abilities, though specific komoot routes on it aren't detailed here.
There are over 10 road cycling routes around Bennington detailed in komoot, offering a variety of experiences for different skill levels. These include routes ranging from moderate to difficult, showcasing the region's diverse landscape.
For those seeking a challenge, Bennington offers several difficult routes. One notable option is the Hoosic River loop from Bennington, a difficult 51.1-mile (82.2 km) path that follows the Hoosic River and provides views of the surrounding mountain ranges. Another challenging ride is the Bennington Battle Monument β Cold Spring Preserve loop from Bennington, which covers 72.4 miles (72.4 km) with significant elevation gain.
Bennington's road cycling routes often pass by significant historical landmarks and natural features. You can cycle past historic covered bridges like the Silk Covered Bridge. Routes may also lead to or offer views of the Bennington Battle Monument, which commemorates a Revolutionary War battle and provides expansive views. The region's natural beauty includes lakes such as Lake Paran and Lake Shaftsbury, and the Walloomsac River, which offer tranquil scenery.
Yes, several routes are designed to feature the historic covered bridges. A popular choice is the Silk Covered Bridge loop from North Bennington, a 33.6-mile (54.1 km) trail that specifically incorporates these architectural gems. Another option is the Bingham Hill β Silk Covered Bridge loop from Shaftsbury, which also passes a covered bridge.
The best time for road cycling in Bennington is generally from spring through fall. Autumn is particularly spectacular, with vibrant foliage displays as routes meander through wooded areas. The cooler temperatures and stunning colors make for a memorable cycling experience. Summer offers warm weather and lush greenery, while spring brings fresh blooms.
Road cyclists often praise Bennington for its blend of natural beauty, varied terrain, and historic charm. The opportunity to combine physical activity with historical appreciation, such as cycling past covered bridges and historic sites, is a highlight. The region's rolling hills and mountain views provide engaging rides, and the active local cycling community adds to its appeal.
Yes, many routes in the Bennington area incorporate scenic waterways. For instance, the Hoosic River loop from Bennington directly follows the Hoosic River, offering picturesque views. Other routes may pass by tranquil bodies of water like Lake Paran and Lake Shaftsbury, providing serene landscapes.
While specific parking locations for each trailhead are not detailed here, many routes around Bennington, North Bennington, and Shaftsbury typically start from areas where public parking is available. It's advisable to check the starting point of your chosen komoot route for specific parking recommendations or local town parking options.
Yes, the topography around Bennington, with its rolling hills and proximity to the Green and Taconic Mountains, means many routes offer opportunities for panoramic views. Sustained climbs into areas like Stamford and Savoy can lead to expansive vistas. The Bennington Battle Monument itself offers breathtaking views from its observation deck, and routes designed to pass by it will provide similar scenic rewards.


Browse the best Road cycling routes in other regions.