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5
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Touring cycling routes around North Bennington feature diverse terrain set against the Green Mountains and Taconic Mountains. The region includes rolling hills, significant elevation changes, and both paved and unpaved sections. Scenic lakes like Lake Paran and rivers such as the Walloomsac and Battenkill are often integrated into routes. Woodlands and historic covered bridges, like the Silk Covered Bridge, characterize the landscape.
Last updated: June 28, 2026
2
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
20.9km
01:16
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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1
riders
18.7km
01:07
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
1
riders
34.4km
02:28
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around North Bennington
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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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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There are 5 touring cycling routes available around North Bennington. These routes offer a variety of experiences, from easy rides to more challenging adventures.
You can expect diverse terrain, including rolling hills and significant elevation changes, set against the stunning backdrop of the Green Mountains and Taconic Mountains. Routes often feature a mix of paved and unpaved sections, with scenic views of valleys, rivers like the Walloomsac and Battenkill, and extensive woodlands. Historic covered bridges, such as the Silk Covered Bridge, are also common features.
Yes, there is one easy touring cycling route available. The Bennington Battle Monument loop from Old Bennington is a great option, covering 18.7 km with moderate elevation gain, making it suitable for those looking for a less strenuous ride. The region also offers flatter options like the Bennington Rail Trail and Walloomsac Riverwalk, which are ideal for casual cycling.
For more advanced cyclists, there are 3 difficult touring cycling routes. A challenging option is the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington, which spans 38.2 km with significant elevation gain of almost 700 meters. Another demanding route is the Bennington Battle Monument loop from Bennington, covering 34.4 km with over 550 meters of ascent.
Many routes offer views of iconic landmarks and natural features. You can cycle past the historic Bennington Battle Monument, cross the picturesque Silk Covered Bridge, or explore the Carriage Road (Grove Road). The area also features the Wooden Footbridge and offers views towards Harmon Hill. Routes often incorporate views of working farms, tranquil lakes like Lake Paran, and the scenic Walloomsac and Battenkill Rivers.
Yes, some touring cycling routes in the area incorporate gravel sections, offering a mixed-surface experience. For example, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington combines paved and gravel roads, providing views of working farms and historic landmarks.
The best time for touring cycling in North Bennington is generally from spring through fall. During these seasons, the weather is pleasant, and the natural beauty of the Green Mountains and surrounding landscapes is at its peak. Autumn offers particularly stunning foliage views.
All the touring cycling routes listed are designed as loops, allowing you to start and end at the same point. This includes routes like the Bike loop from Bennington and the various Bennington Battle Monument loops, providing convenient circular journeys.
The touring cycling routes around North Bennington vary in distance to suit different preferences. They range from approximately 18.7 kilometers (11.6 miles) for easier loops to about 38.2 kilometers (23.7 miles) for more challenging rides, offering options for both shorter excursions and longer adventures.
While specific ratings are not available for these routes, the region is highly regarded for its diverse terrain, picturesque landscapes, and historical charm. Cyclists often praise the blend of challenging ascents and leisurely trails, the stunning views of the Green Mountains, and the unique character added by historic covered bridges and working farms.


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