37
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11
rides
Road cycling around North Bennington, Vermont, offers a diverse landscape characterized by varied terrain and significant elevation changes. The region features predominantly paved surfaces, with some routes incorporating unpaved sections for added variety. Cyclists can expect to encounter historic covered bridges, scenic lakes like Lake Paran, and verdant woods, all set against the backdrop of the Green Mountains. The area provides options for different fitness levels, from moderate loops to challenging rides with substantial climbs.
Last updated: July 12, 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.

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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.
5
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.
3
riders
41.0km
02:54
550m
550m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around North 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.
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Site of the first confrontation between the Green Mountain Boys and the "Yorker" Sheriff and posse. at the Breckenridge Farm.
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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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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.
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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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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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Road cycling around North Bennington offers a diverse landscape with varied terrain. You'll find predominantly paved surfaces, but some routes may include unpaved sections for added variety. Expect rolling hills and significant elevation changes, ranging from moderate climbs to more demanding ascents, all set against the backdrop of the Green Mountains.
Yes, North Bennington offers options for various fitness levels. While many routes involve elevation changes, there are easier options available. For example, the guide includes one easy route among its 11 road cycling tours, and other routes like the Silk Covered Bridge loop from North Bennington are rated as moderate, offering a manageable 560m elevation gain over 54.1 km.
The region is renowned for its picturesque covered bridges. The Silk Covered Bridge loop from North Bennington and the Bingham Hill β Silk Covered Bridge loop from Shaftsbury both prominently feature the historic Silk Covered Bridge, which spans the Walloomsac River. Another route, the Bennington Battle Monument β Silk Covered Bridge loop from Bennington, also passes by this iconic landmark.
Absolutely. Many routes allow you to incorporate historical sites. The Bennington Battle Monument β Silk Covered Bridge loop from Bennington is a challenging ride that includes the significant Bennington Battle Monument. The wider region also features the Park-McCullough House, a well-preserved Victorian-era mansion with scenic grounds.
Yes, the area offers stunning natural beauty. Routes often provide mountain vistas, as North Bennington is nestled in the Green Mountains. You can also find routes that pass by Harmon Hill, offering panoramic views. Lake Paran in North Bennington is another scenic highlight, known for its clean water and natural setting, which can be a refreshing stop on your ride.
Experienced riders will find plenty of challenging options. Five of the 11 routes in the guide are rated as difficult, featuring significant elevation gains. For instance, the Hoosic River loop from Bennington is a difficult 82.2 km path with over 1,000m of elevation gain, while the Bennington Battle Monument β Cold Spring Preserve loop from Bennington also presents a substantial challenge with over 1,000m of ascent.
The region is beautiful throughout the warmer months. Spring and summer offer lush greenery, while autumn is particularly spectacular for fall foliage rides, with vibrant colors transforming the landscape. Cyclists can enjoy the scenic byways and country roads during these seasons, though conditions can vary.
Yes, many of the road cycling routes around North Bennington are designed as loops, allowing you to start and end at the same point. Examples include the popular Silk Covered Bridge loop from North Bennington and the Hoosic River loop from Bennington, providing convenient circular journeys.
Beyond the Green Mountains and covered bridges, you can encounter several natural features. Lake Paran offers a tranquil setting, and the Mile-Around Woods in North Bennington is a popular trail known for wildflowers and mountain views. Thurber Pond also provides scenic views and opportunities for wildlife spotting along certain routes.
While specific parking locations for each route are not detailed here, North Bennington and nearby towns generally offer public parking options. Many routes start from or pass through areas where parking is accessible, such as town centers or designated trailheads. It's advisable to check local parking regulations for your chosen starting point.
For families, while many road cycling routes involve significant distances and elevation, some shorter, less challenging options or paved trails might be suitable. The Robert Frost Trail, a two-mile packed dirt path extending from Lake Paran to Route 7A in Shaftsbury, is suitable for walking and cycling, offering a gentler experience away from main roads.
The komoot community frequently praises the diverse landscape, which combines historic covered bridges, rolling hills, and stunning mountain vistas. Cyclists appreciate the variety of routes catering to different ability levels, from moderate loops to more challenging ascents, making it a rewarding destination for exploring Vermont's natural beauty.


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