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Touring cycling in Glastenbury Wilderness offers routes through the surrounding southern Vermont landscape. The region features mountainous terrain, dense forests, and scenic valleys. While cycling is not permitted within the designated wilderness area, the adjacent areas provide varied terrain with both paved and unpaved roads. These routes often include significant elevation changes, characteristic of the Green Mountain National Forest.
Last updated: July 12, 2026
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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
34.4km
02:28
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
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 Glastenbury Wilderness
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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While touring cycling is not permitted within the Glastenbury Wilderness itself, the surrounding southern Vermont region offers a mix of paved and unpaved roads. You'll encounter varied terrain, from scenic valley roads to hilly sections that can be quite challenging, often requiring significant elevation gain.
Yes, the region around Glastenbury Wilderness is known for its challenging routes. For instance, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington is a difficult 30.8 km route with over 520 meters of elevation gain, incorporating gravel sections. Another demanding option is the Bennington Battle Monument loop from Bennington, covering 34.4 km with 550 meters of ascent.
Yes, there is an easy touring cycling route available. The Bennington Battle Monument loop from Old Bennington is an easy 18.7 km route with just under 140 meters of elevation gain, making it a good option for those looking for a less strenuous ride.
While the immediate wilderness area is rugged, the broader region of southern Vermont offers cycling experiences suitable for families. For an easier option, consider the Bennington Battle Monument loop from Old Bennington, which is rated as easy and covers a manageable distance.
While the Glastenbury Wilderness itself has specific regulations for non-mechanized recreation, the surrounding touring cycling routes are generally on public roads or designated trails. It's always best to keep dogs leashed and ensure they are well-behaved, especially on shared paths or near farms. Always check local signage for specific rules regarding pets.
Yes, all the touring cycling routes in this guide are loops, making them convenient for starting and ending at the same location. Examples include the Bike loop from Bennington and the various Bennington Battle Monument loops.
Many of the touring cycling routes in this guide start from Bennington or Old Bennington. You can typically find parking in these towns, often near local attractions or public spaces, before beginning your ride. Always check local parking regulations.
Many routes in the area, such as the Bennington Battle Monument loop from Bennington, feature the historic Bennington Battle Monument. The surrounding region is also known for its outstanding scenery, including the valleys of the Battenkill, Otter Creek, and Mettawee River, offering picturesque views of Vermont's natural landscape.
The best time for touring cycling in southern Vermont, including the area around Glastenbury Wilderness, is typically from late spring through early autumn. During these seasons, the weather is generally pleasant, and the fall foliage offers spectacular views. Always check current weather conditions before heading out, especially for unpaved sections.
Yes, some routes incorporate gravel road sections. For example, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington explicitly mentions gravel roads, adding a different dimension to the cycling experience. Be prepared for varied surfaces if you choose these routes.
The dense forests and natural areas surrounding Glastenbury Wilderness are home to a variety of wildlife. While cycling, you might spot various bird species, and it's possible to see signs of black bears, which are common in the region. Always maintain a respectful distance from any wildlife you encounter.


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