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5
rides
Touring cycling routes around Bennington traverse a varied landscape, situated between the Green Mountains and the Taconic Mountains. The region features diverse terrain, including challenging climbs and rolling roads through mountainous areas. Picturesque river valleys, such as those carved by the Walloomsac and Battenkill Rivers, offer gentler routes. Extensive woodlands provide shaded paths and a sense of immersion in nature.
Last updated: May 5, 2026
19.6km
01:28
90m
90m
Embark on the Hillsborough Recreational Rail Trail Loop for an easy touring bicycle ride spanning 12.2 miles (19.6 km). You will gain 306 feet (93 metres) in elevation, typically completing…
44.0km
03:01
500m
500m
Embark on a challenging touring bicycle adventure connecting Greenfield State Park and Wapack National Wildlife Refuge. This difficult 27.3-mile (44.0 km) loop will have you gaining 1651 feet (503 metres)…

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34.7km
02:51
480m
480m
A difficult 21.6-mile gravel cycling loop from Deering Lake to Francestown, featuring rugged Class VI roads and 1589 feet of elevation gain.
3
riders
41.8km
03:19
530m
530m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
31.5km
02:05
350m
350m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Bennington
The Crotched Mountain Road surrounds the Francestown forest and takes you on an enjoyable ride below the canopy.
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The Crotched mountain road surrounds the Francestown town forest and takes you on an enjoyable ride below the canopy.
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This road rounds the beautiful landscape of the Wapack National wildlife refuge. It offers the opportunity to ride along the forest and have a nice day out outdoor.
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This railroad converted to cycling path is perfect for a pleasant ride along the river.
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Komoot features over 5 touring cycling routes around Bennington. These routes traverse varied landscapes, offering options for different skill levels and preferences.
Touring cycling routes in Bennington offer a diverse terrain. You'll find challenging climbs and rolling roads through the Green Mountains and Taconic Mountains, as well as gentler paths through picturesque river valleys like those carved by the Walloomsac and Battenkill Rivers. Extensive woodlands also provide shaded routes and a sense of immersion in nature.
Yes, Bennington offers routes suitable for easier rides and families. The Hillsborough Recreational Rail Trail Loop is an easy 12.2-mile (19.6 km) trail that provides a gentle path. Additionally, the Robert Frost Trail, extending from Lake Paran, offers an easy and scenic option through wetlands and forests, suitable for cyclists.
Absolutely. For experienced riders seeking a challenge, Bennington provides routes with significant elevation changes and diverse scenery. Examples include the Greenfield state park to Wapack National Wildlife Refuge loop, a difficult 27.3-mile (44.0 km) path, and the Pleasant Pond loop from Bennington, which covers 41.8 km with substantial climbing.
Many routes in the Bennington area incorporate historic sites and natural landmarks. The Bennington Battle Monument is a frequent feature, and you can find routes that pass through charming covered bridges. Natural attractions like Woodford State Park and Lake Shaftsbury State Park also offer tranquil settings and opportunities for exploration.
Yes, the region offers access to several rail trails, which typically provide flatter and often paved or hard-packed surfaces ideal for touring cyclists. The Hillsborough Recreational Rail Trail Loop is a prime example. The Delaware-Hudson Rail Trail also has segments suitable for touring bikes, and the Ashuwillticook Rail Trail in Massachusetts is known for its scenic views.
Bennington is rich in natural beauty. You can cycle to or near Woodford State Park, known for its nature trails and cold lake, or Lake Shaftsbury State Park, which boasts a gorgeous lake with a beach and a mile-long trail. Lake Paran is another small lake offering lovely scenery. The Robert Frost Trail also provides a scenic ride through wetlands and forests.
Yes, for those who enjoy gravel cycling, Bennington offers options. The Deering Lake to Francestown gravel loop is a 21.6-mile (34.7 km) trail that leads through varied terrain, perfect for a gravel touring experience.
Bennington offers cycling opportunities across multiple seasons. While specific recommendations depend on personal preference, the region's diverse landscapes are particularly beautiful in spring, summer, and fall. Summer offers access to lakes for swimming, while fall brings stunning foliage. Some trails, like those in the Bennington Area Trail System, are also used for cross-country skiing in winter, suggesting varied seasonal use.
Yes, there are routes that offer a balanced challenge. The Campbell Hill – Bell Ledges loop from Greenfield is a moderate 32.4 km route, providing a good option for those looking for something between easy and difficult.
Yes, many of the touring cycling routes around Bennington are designed as loops, allowing you to start and end at the same point. Examples include the Hillsborough Recreational Rail Trail Loop, the Greenfield state park to Wapack National Wildlife Refuge loop, and the Deering Lake to Francestown gravel loop.


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