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If you've ever tried to plan touring cycling around Bennington, you know how overwhelming the options can be. With so many roads and trails, it's hard to tell which routes are genuinely worth your time and effort, and which are just filler. We get it β you want the good stuff, not endless guesswork. That's where komoot comes in. Our community has ridden, mapped, and reviewed these routes, so we've done the legwork to bring you a curated shortlist ofβ¦
Last updated: June 4, 2026
2
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.

1
riders
18.7km
01:07
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
1
riders
34.4km
02:28
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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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Touring cycling routes in Bennington are generally considered challenging. All routes listed in this guide are rated as 'difficult', featuring significant elevation gains and varied terrain. For example, the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Pownal includes over 689 meters of elevation gain.
While the routes highlighted in this guide are rated as difficult, Bennington does offer options for families. The Bennington Area Trail System (BATS) includes trails like the Carriage Road, which provides sweeping valley views and is considered more beginner-friendly. The Bennington Rail Trail also offers a dedicated path suitable for a more relaxed family ride.
You can expect a diverse mix of terrain, including challenging climbs, rolling roads, and extensive wooded areas. Many routes, such as the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington, feature gravel sections. The region's location between the Green and Taconic Mountains means varied surfaces and elevation changes are common.
Bennington's routes offer breathtaking vistas of valleys, rivers like the Walloomsac and Battenkill, and the surrounding mountainous countryside. You'll cycle through woodlands and past beautiful water bodies such as Lake Paran and Woodford Lake. The 1753 House β Bennington Battle Monument loop from Williamstown, for instance, takes you through varied and scenic landscapes.
Yes, Bennington is rich in history. A prominent landmark you'll encounter is the Bennington Battle Monument, which is featured on several routes, including the Carpenter Hill β Bennington Battle Monument loop from Bennington. You might also come across historic covered bridges, adding a cultural dimension to your ride.
Many of the popular touring cycling routes around Bennington are designed as loops, offering a convenient way to start and end your ride at the same location. Examples include the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Pownal and the Bennington Battle Monument β Vermont Working Farm (Gravel Road) loop from Bennington.
The region's natural beauty, with its woodlands and mountainous terrain, suggests that spring, summer, and fall offer excellent conditions for touring cycling. Autumn, in particular, would provide stunning foliage views. Always check local weather conditions before heading out.
While specific parking details for each route are best checked on individual tour pages, Bennington generally offers access points for its trail systems. The Bennington Bike Hub can also provide resources and information on local rides and access points, suggesting that parking is available near popular trailheads.
The provided information does not detail specific public transport options directly to cycling paths. It is advisable to check local Bennington public transportation services or consider driving to a suitable starting point for your chosen route.
Touring cyclists frequently praise the diverse landscapes, from challenging mountain climbs to scenic river valleys and extensive woodlands. The integration of historic sites like the Bennington Battle Monument into routes also adds a unique appeal. The area's well-maintained trail systems and variety of routes cater to different preferences, making it a popular destination for those seeking both adventure and natural beauty.
Yes, the Bennington area is known for its charming covered bridges. While not explicitly on every route in this guide, the region research mentions a 14.5-mile Covered Bridge Ride, indicating that these historic structures can be incorporated into your cycling adventures. The Silk Covered Bridge is one such highlight in the vicinity.
While specific 'less crowded' trails are not detailed, the Bennington Area Trail System (BATS) and the Bennington Rail Trail offer a network of paths. Exploring routes that might be slightly off the main tourist paths or cycling during off-peak hours could lead to a more serene experience. The region's extensive woodlands also provide a sense of immersion in nature, potentially offering quieter sections.


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