35
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3
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Road cycling in Glastenbury Wilderness offers routes through the scenic landscapes bordering this protected area. The region is characterized by hilly terrain, dense forests of fir and spruce, and views of mountain summits, including Glastenbury Mountain. While direct cycling within the wilderness is not permitted, surrounding roads like Route 9 and U.S. Route 7 provide significant elevation changes and tranquil rides through the Vermont countryside. These routes allow cyclists to experience the wild character of the Green Mountains.
Last updated: October 4, 2026
5.0
(1)
5
riders
24.8km
01:10
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
73.4km
03:35
770m
770m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

1
riders
35.0km
01:40
420m
420m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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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 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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Lake Paran is an excellent spot to take a break along your ride. Considered to be the best lake in the area with the cleanest water, it certainly makes a great spot to have a mid ride dip or refuel.
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There are 3 dedicated no-traffic road cycling routes featured in this guide that explore the scenic areas surrounding the Glastenbury Wilderness. These routes offer a mix of easy and moderate challenges for road cyclists.
The routes around Glastenbury Wilderness are characterized by hilly terrain with significant elevation changes, offering challenging climbs and descents. You'll cycle through dense forests of fir, spruce, and beech, enjoying the natural beauty and shade. The region, part of Bennington County, provides diverse terrain including rolling roads and scenic river valleys.
Yes, there is one easy route available. The Roadbike loop from Bennington is a great option, covering approximately 24.8 kilometers with an elevation gain of around 293 meters, making it suitable for those looking for a less strenuous ride.
For a moderate challenge, consider the Battenkill Start Line β Silk Covered Bridge loop from South Shaftsbury, which is about 73.4 kilometers long with over 770 meters of elevation gain. Another moderate option is the Roadbike loop from Horst Maple Farm, spanning nearly 35 kilometers with around 422 meters of climbing.
While cycling on the roads bordering the wilderness, you'll encounter views of the Green Mountains, including Glastenbury Mountain. The region is known for its dense forests and remote character. Scenic Byways like Route 9 (Molly Stark Byway) offer sights such as the Hogback Scenic Overlook with its 100-mile view, and charming covered bridges.
Absolutely. The presence of the Appalachian Trail and Long Trail traversing the wilderness highlights the region's wild nature. While these are hiking trails, their proximity to cycling routes, such as a section of paved Route 9 that is part of a loop including portions of these trails, allows for multi-sport adventures. You can appreciate the untamed landscape from your bike and then explore on foot.
The best time for road cycling in this region is typically during the warmer months, from late spring through early autumn. This period offers pleasant temperatures, vibrant foliage, and generally clear road conditions, allowing you to fully enjoy the scenic byways and forest-lined roads.
The 'easy' rated route, the Roadbike loop from Bennington, is the most suitable option for families or those seeking a less challenging ride. Its shorter distance and moderate elevation make it more accessible.
Parking is generally available in the towns and villages that serve as starting points for these routes, such as Bennington or South Shaftsbury. It's advisable to check specific parking availability for your chosen route's trailhead or starting location.
While the routes themselves focus on no-traffic roads through natural settings, you will find amenities like cafes and restrooms in the charming historic villages and vibrant downtowns that these scenic byways often pass through or connect. Plan your stops in towns like Bennington for services.
The remote and wild character of the Glastenbury Wilderness area naturally translates to less traffic on the surrounding rural roads. This allows road cyclists to immerse themselves in the tranquility of the Vermont countryside, enjoying scenic stretches of pavement with fewer disturbances.

