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Road cycling routes
United States
Vermont
Bennington County

Glastenbury Wilderness

The best road cycling routes in Glastenbury Wilderness

35

riders

11

rides

Road cycling routes in Glastenbury Wilderness navigate the scenic areas surrounding the designated wilderness, which is part of the Green Mountain National Forest. The region is characterized by dense forests, significant elevation changes, and a blend of mountainous and hilly terrain. Cyclists can expect routes that traverse quiet back roads, offering views of the picturesque landscapes and challenging ascents. The area's geography provides varied terrain suitable for experienced road cyclists.

Best road cycling routes in Glastenbury Wilderness

  • The most popular…

Last updated: June 1, 2026

9

riders

#1.

Hoosic River loop from Bennington

82.2km

03:53

1,100m

1,100m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Hard

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard
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Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Cycling in Glastenbury Wilderness

Tips from the Community

Felix
June 20, 2025, Natural Bridge State Park Waterfalls

Probably more impressive to ride/drive up through McCauley Road. You can also access it from Natural Bridge or Hudson Brook Lane Road on foot or on a bike (which is what we did). White marble natural bridges/quarries are apparently not very common in the North America. Worth the detour if you are in North Adams.

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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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Alex
February 8, 2024, 1753 House

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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Alex
January 31, 2024, Thurber Pond

Cycling on this good quality road next to Thurber Pond is a joy with the pond directly in view. Keep your eyes peeled for the various pond life and birds that live around it.

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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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Alex
January 26, 2024, Silk Covered Bridge

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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Frequently Asked Questions

What is the typical difficulty level for road cycling routes in the Glastenbury Wilderness area?

The road cycling routes in the Glastenbury Wilderness area are primarily suited for experienced cyclists due to the region's mountainous and hilly terrain. Out of 11 available routes, 5 are classified as difficult and 5 as moderate, with only 1 easy route. Expect significant elevation changes and challenging ascents on many of the paths.

When is the best time of year to go road cycling near Glastenbury Wilderness?

The best time for road cycling near Glastenbury Wilderness is typically from late spring through early autumn. During these months, the weather is generally mild, and the scenic Vermont countryside is at its most vibrant. Fall offers spectacular foliage, making it a particularly popular time, though routes can be challenging with cooler temperatures.

Are there any family-friendly road cycling routes in the Glastenbury Wilderness area?

While many routes in the Glastenbury Wilderness area are challenging, there is one easy route available. For families or those seeking a less strenuous ride, it's best to look for routes with minimal elevation gain and shorter distances. Always check the route details for specific difficulty and distance before heading out.

What kind of landscapes can I expect to see while road cycling in the Glastenbury Wilderness region?

Road cycling in the Glastenbury Wilderness region offers stunning natural beauty. You'll traverse quiet back roads through dense forests of balsam fir, red spruce, birch, and beech. The mountainous terrain provides expansive views, and you may encounter serene ponds and small streams. The area is known for its pristine natural beauty and picturesque landscapes.

Are there any loop road cycling routes available in the Glastenbury Wilderness area?

Yes, many of the road cycling routes in the Glastenbury Wilderness area are designed as loops, allowing you to start and end at the same point. For example, the Hoosic River loop from Bennington and the Bennington Battle Monument – Cold Spring Preserve loop from Bennington are popular loop options, offering comprehensive tours of the region's scenery.

What are some of the longer, more challenging road cycling routes in the area?

For experienced cyclists seeking a challenge, routes like the Hoosic River loop from Bennington cover over 51 miles with significant elevation gain. Another demanding option is the Bennington Battle Monument – Silk Covered Bridge loop from Bennington, which is nearly 49 miles long and leads through forested areas and past historic sites.

Can I find moderate-difficulty road cycling routes near Glastenbury Wilderness?

Yes, there are several moderate-difficulty road cycling routes available. For instance, the Bingham Hill – Silk Covered Bridge loop from Bennington offers a moderate challenge over approximately 23 miles, with a manageable elevation gain. Another moderate option is the Bingham Hill – Silk Covered Bridge loop from Shaftsbury, which is longer at 45 miles but still rated moderate.

Are there any historical or intriguing points of interest along the road cycling routes?

While cycling, you might pass by areas with historical significance, such as the Bennington Battle Monument, which is featured in several route names. The region itself holds a sense of mystery, with remnants of the Glastenbury Ghost Town nearby and local lore about the 'Bennington Triangle,' adding an element of intrigue to your ride.

What kind of wildlife might I encounter while road cycling in this region?

The Glastenbury Wilderness area and its surroundings provide critical habitat for diverse wildlife. While cycling, you might spot white-tailed deer, moose, or various bird species. Black bears and bobcats also inhabit the area, so it's always wise to be aware of your surroundings and practice wildlife safety.

Is it possible to access road cycling routes near Glastenbury Wilderness using public transport?

Accessing road cycling routes directly via public transport can be limited in this rural area. Most cyclists typically drive to a starting point, such as Bennington, which serves as a common departure for many routes, and park their vehicles there. It's advisable to plan your transport in advance.

Where can I find parking for road cycling routes in the Glastenbury Wilderness area?

Many road cycling routes in the Glastenbury Wilderness area start from towns like Bennington or Shaftsbury. These towns typically offer public parking options where you can leave your vehicle while you embark on your ride. Always check local regulations for parking availability and restrictions.

Are there cafes or pubs near the road cycling routes for a break?

As many routes start and end in or pass through towns like Bennington, you'll find various cafes, pubs, and restaurants where you can take a break, refuel, and enjoy local hospitality. It's a good idea to plan your route to include stops in these towns for refreshments.

What makes Vermont a good destination for road cycling, particularly around Glastenbury Wilderness?

Vermont is recognized as an international cycling destination, known for its scenic and quiet back roads. The region around Glastenbury Wilderness offers a blend of pristine natural beauty and challenging mountainous terrain, providing rewarding routes for experienced road cyclists. The diverse landscapes and significant elevation changes make for a varied and engaging cycling experience.

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