The best cycling routes around Old Bennington
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Touring cycling around Old Bennington, Vermont, features routes that navigate through varied terrain, including rolling hills and rural landscapes. The region is characterized by its historical landmarks, such as the Bennington Battle Monument, and working farms. Routes often incorporate a mix of paved roads and gravel sections, offering diverse cycling experiences. The elevation gains on some routes indicate a hilly topography, providing both scenic views and physical challenges.
Best touring cycling routes around Old Bennington
- The most popular touring cyclingβ¦
Last updated: July 2, 2026
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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20.9km
01:16
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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18.7km
01:07
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Old Bennington
Tips from the Community
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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Mohawk Trail Multiuse Path is an almost 5-mile long trail near Williamstown. The trail is mostly flat and at times, gives you good views of the Housatonic River.
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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 beautiful Hoosic River runs through three states and is fed by streams from the Green Mountains of Vermont, the Taconics of New York and the lofty sides of Mount Greylock, the highest peak in Massachusetts (3,491 ft.). Its meandering journey travels 70 miles from where it begins at the Cheshire Reservoir in Massachusetts, to where it eventually enters the Hudson River at Stillwater, NY.
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Wonderful view from the monument into the distance.
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come between 10 and 5 to see the top of the monument.
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Frequently Asked Questions
How many touring cycling routes are available around Old Bennington?
There are several touring cycling routes around Old Bennington, offering a mix of easy and challenging options for various skill levels.
Are there any easy touring cycling routes suitable for beginners in Old Bennington?
Yes, for an easier ride, consider the Bennington Battle Monument loop from Old Bennington. This 18.7 km (11.6 miles) route is rated easy and takes about 1 hour 7 minutes to complete, offering views of the historic monument.
What kind of terrain can I expect on touring cycling routes in Old Bennington?
The routes around Old Bennington feature varied terrain, including rolling hills and rural landscapes. You'll encounter a mix of paved roads and gravel sections, with some routes leading through working farm areas. Expect notable elevation changes on many of the longer, more challenging rides.
Are there any circular touring cycling routes in the Old Bennington area?
Yes, many of the touring cycling routes in Old Bennington are loops. For example, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Pownal is a popular circular option that takes you through farm areas.
What are some scenic viewpoints or landmarks I can see along the cycling routes?
Old Bennington's routes often pass by historical landmarks and natural beauty. You can expect to see the Bennington Battle Monument, and some routes may lead you near the Silk Covered Bridge or offer views from Harmon Hill.
Are there any touring cycling routes that follow a river?
Yes, the Bennington Battle Monument β Hoosic River loop from The Clark Art Institute is a challenging 62.2 km (38.6 miles) route that includes sections along the Hoosic River, offering diverse landscapes.
What is the best season for touring cycling in Old Bennington?
While specific recommendations depend on personal preference, the region's rolling hills and rural landscapes are particularly beautiful in spring, summer, and fall. Autumn offers vibrant foliage, though some gravel sections might be affected by weather. Winter cycling is possible but requires appropriate gear and awareness of conditions.
Are there any routes that go through working farm areas?
Absolutely. The Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington is a great example, taking you through picturesque working farm landscapes on a mix of paved and gravel roads.
What do other touring cyclists enjoy most about cycling in Old Bennington?
The komoot community frequently praises the region for its blend of historical landmarks, such as the Bennington Battle Monument, and the serene rural farm roads. Cyclists appreciate the varied terrain, which offers both scenic views and physical challenges, making for a rewarding experience.
Are there any longer, more challenging touring cycling routes for experienced riders?
Experienced riders will find several challenging options. For instance, the Carpenter Hill β Bennington Battle Monument loop from Bennington is a difficult 34.9 km (21.7 miles) route with significant elevation gain, providing a robust workout and scenic rewards.
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