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Gravel biking in the Glastenbury Wilderness region offers extensive opportunities on unpaved roads surrounding the federally protected area. The landscape features hilly and mountainous terrain with dense forests of balsam fir, red spruce, and various hardwoods. While mechanical transport is restricted within the designated Wilderness, the surrounding areas provide a network of gravel roads with varied elevation changes and scenic views. This region is characterized by its remote backcountry feel, numerous small creeks, and diverse wildlife habitats.
Last updated: May 13, 2026
3
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
26.1km
01:36
390m
390m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
45.9km
02:46
660m
660m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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It's important to note that bicycles, including gravel bikes, are generally prohibited within the federally protected Glastenbury Wilderness Area to preserve its primitive character. However, the surrounding areas of Vermont, particularly near towns like Bennington and Shaftsbury, offer an extensive network of unpaved roads perfect for traffic-free gravel biking experiences.
The terrain in the broader Vermont area near Glastenbury Wilderness is characterized by rolling hills and mountainous features, offering both scenic beauty and challenging climbs. You'll encounter dense forests, working farms, and stunning views of the Green Mountains. The routes often feature a mix of well-maintained gravel roads and some more rugged sections.
This guide features three distinct no-traffic gravel bike routes in the areas surrounding Glastenbury Wilderness. These routes offer varying distances and difficulty levels, providing options for different riding preferences.
The routes in this guide vary in length and duration. For example, the Millers Pond loop from Hale Mountain is about 26 kilometers long and takes around 1 hour 35 minutes. Longer options, like the Millers Pond loop from Shaftsbury, stretch to nearly 46 kilometers and can take over 2 hours 45 minutes to complete.
While many routes in the region can be challenging, the Millers Pond loop from Hale Mountain is rated as moderate, making it a good option for riders looking for a less strenuous experience compared to the more difficult routes in the area. It still offers beautiful scenery without excessive technical demands.
Experienced gravel bikers looking for a challenge will enjoy routes like the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington, which is rated difficult and covers nearly 40 kilometers with significant elevation gain. Another demanding option is the Millers Pond loop from Shaftsbury, a difficult 46-kilometer ride.
Yes, all the gravel bike routes featured in this guide are designed as loops. This means you'll start and end at the same point, making logistics for parking and transportation straightforward.
The best time for gravel biking in the broader Vermont area is typically from late spring through early fall (May to October). During these months, the weather is generally pleasant, and the gravel roads are usually in good condition. Fall offers spectacular foliage, making it a particularly scenic time to ride.
While you won't be riding directly within the Glastenbury Wilderness, the surrounding forested areas are rich in wildlife. You might spot various bird species, and it's also critical black bear habitat. Keep an eye out for deer and other forest creatures, especially during dawn and dusk.
The routes often pass through areas with stunning views of the Green Mountains and the picturesque Vermont landscape, including working farms and dense forests. While there are no specific highlights linked in this guide, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington passes near the historic Bennington Battle Monument, offering a cultural landmark alongside natural beauty.
While the routes are generally traffic-free, their difficulty ratings (moderate to difficult) and distances mean they might be more suitable for families with older, experienced riders. For those with dogs, it's essential to ensure your dog is well-trained, can keep pace, and that you adhere to local leash laws and carry waste bags. Always check specific trail regulations for pets.
Since the routes are loops starting from towns like Bennington and Shaftsbury, you can typically find parking in or near these communities. It's advisable to check local parking regulations and availability in advance, especially during peak seasons.


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