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Routes
Road cycling routes
United States
Vermont
Bennington County

Pownal Center

The best road cycling routes around Pownal Center

4.7

(5)

290

riders

23

rides

Road cycling routes around Pownal Center are set within southwestern Bennington County, offering access to the Green Mountains and the Hoosic River valley. The terrain features a mix of rolling hills and varying elevation gains, with well-paved surfaces suitable for road bikes. Cyclists can expect routes that traverse scenic landscapes, including river valleys and areas leading towards higher elevations. The region provides diverse options for different fitness levels, from moderate rides to more challenging climbs.

Best road cycling routes around…

Last updated: May 16, 2026

33

riders

#1.

Mount Greylock loop from The Clark Art Institute

39.1km

02:19

910m

910m

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

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Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

9

riders

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

Hard
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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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Mohawk Trail Multiuse Path is an almost 5-mile long trail near Williamstown. The trail is mostly flat and at times, gives you good views of the Housatonic River.

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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

How many road cycling routes are available around Pownal Center?

Pownal Center offers over 20 road cycling routes, catering to various skill levels. You'll find a good mix of easy, moderate, and difficult rides to explore the region's diverse landscapes.

What kind of terrain can I expect on road cycling routes in Pownal Center?

The terrain around Pownal Center features a mix of rolling hills and varying elevation gains. Routes often follow well-paved surfaces through scenic river valleys, like the Hoosic River, and lead towards higher elevations in the Green Mountains and Taconics, providing both challenging climbs and enjoyable descents.

Are there any challenging road cycling routes with significant elevation gain?

Yes, Pownal Center offers several challenging routes. For instance, the Mount Greylock loop from The Clark Art Institute is a difficult 24.3-mile ride with over 900 meters of elevation gain, approaching Mount Greylock. You can also find longer, difficult rides like the Hoosic River loop from Bennington, which covers over 82 kilometers with significant climbing.

What are some scenic points of interest I can see while road cycling in Pownal Center?

Road cycling routes in Pownal Center often pass by beautiful natural features and landmarks. You can enjoy views of the Hoosic River, explore areas near the Green Mountains, or pass by cultural sites like The Clark Art Institute. The region is also known for its picturesque scenic drives, such as those along US Route 7 and Vermont's Route 100.

Are there any easy or beginner-friendly road cycling routes in the area?

Absolutely. Pownal Center has several easy routes suitable for beginners or those looking for a more relaxed ride. An example is the Hoosic River loop from The Clark Art Institute, an 18.9-mile trail that takes about 1 hour 20 minutes to complete, leading through the scenic Hoosic River valley with moderate elevation.

What do other road cyclists enjoy most about the routes in Pownal Center?

The road cycling routes in Pownal Center are highly rated by the komoot community, with an average score of 4.7 stars. Cyclists often praise the diverse terrain, from rolling hills to challenging climbs, and the beautiful scenic landscapes, including river valleys and views towards the Green Mountains.

Are there any loop routes for road cycling in Pownal Center?

Yes, many road cycling routes in Pownal Center are designed as loops, offering varied scenery without retracing your path. Examples include the Cold Spring Preserve loop from The Clark Art Institute and the Bennington Battle Monument – Silk Covered Bridge loop from The Clark Art Institute, which provides a longer ride through the local landscape.

What is the best time of year for road cycling in Pownal Center?

The best time for road cycling in Pownal Center is typically from late spring through early autumn. During these seasons, the weather is generally pleasant, and the natural scenery, from lush greenery to vibrant fall foliage, is at its peak. It's always a good idea to check local weather conditions before heading out.

Can I find long-distance road cycling routes around Pownal Center?

Yes, Pownal Center serves as a great starting point for longer road cycling excursions. Routes like the Bennington Battle Monument – Silk Covered Bridge loop from The Clark Art Institute offer a substantial 42.2-mile ride, while the Hoosic River loop from Bennington extends to over 82 kilometers, providing ample distance for endurance cyclists.

Are there any unique natural features to look out for while cycling in the Pownal Center area?

Beyond the scenic Hoosic River and the Green Mountains, the region boasts unique natural sites. Quarry Hill, north of the Hoosic River, is an ecological gem known for its botanical biodiversity, hosting over 40 rare plant species due to its distinct limestone bedrock. While not directly on cycling routes, its presence highlights the rich natural environment of the area. You can learn more about this special site at nature.org.

Is there parking available near the road cycling routes in Pownal Center?

While specific parking details for each route may vary, Pownal Center and nearby towns like Bennington often provide public parking options. Many routes, such as those starting from The Clark Art Institute, typically have accessible parking facilities nearby, making it convenient to begin your ride.

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