53
riders
11
rides
Road cycling around Proctorsville, Vermont, offers a diverse experience characterized by rolling hills and a charming rural landscape. The region features scenic routes that often follow the Black River and incorporate sections of the renowned Route 100. Cyclists can expect a mix of gradual climbs and varied terrain, providing a quintessential Vermont cycling experience through picturesque countryside.
Last updated: July 1, 2026
12
riders
97.3km
04:17
920m
920m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
32.3km
02:17
420m
420m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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4
riders
66.3km
03:02
770m
770m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
33.5km
01:21
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
20.8km
01:14
260m
250m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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Popular around Proctorsville
Billings Farm is an outdoor museum and dairy farm and a hidden gem of Vermont. It is an especially good place to come if you're cycling with children who will love seeing the farm animals up close, especially the herd of Jersey cows with their beautiful big brown eyes.
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This road is a joy to ride whilst it travels through the woods with stunning hills such as Mount Tom providing the backdrop.
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Woodward Reservoir in Plymouth, Vermont, offers a calm setting for cyclists. With its quiet reservoir and rural surroundings, riders can take a leisurely break. The reservoir's laid-back atmosphere and practical amenities, like picnic areas, provide a straightforward spot for cyclists to relax amidst Vermont's natural scenery.
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It is worth pedaling through Lincoln Bridge to truly appreciate the design and craftsmanship that went into its creation. Built in 1877, it was restored in the 1980s to ensure its survival for years to come.
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Billings Farm is an outdoor museum and dairy farm and a hidden gem of Vermont. It is an especially good place to come if you're touring with children who will love seeing the farm animals up close, especially the herd of Jersey cows with their beautiful big brown eyes.
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Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.
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A beautiful wooden bridge that you should have seen when you are around.
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Road cycling around Proctorsville offers a diverse experience with rolling hills, picturesque pastoral views, and sections along the Black River. You'll find a mix of gradual climbs and varied terrain, including parts of the scenic Route 100, providing a quintessential Vermont cycling experience.
Yes, Proctorsville has routes suitable for various skill levels. For an easier ride, consider the Vermont Route 100 scenic views loop from Ludlow. This 33.4 km (20.7 miles) route features a more gentle elevation gain, allowing you to enjoy the scenic beauty without overly strenuous climbs.
For cyclists seeking a greater challenge, routes like the Roadbike loop from Cavendish offer substantial climbs and longer distances. This moderate 66.3 km (41.2 miles) path includes significant elevation gain, providing expansive views of the surrounding Vermont landscape.
Many routes offer views of Vermont's charming rural character, including rolling hills and quaint villages. While cycling, you might pass by historical sites like the Proctorsville Quarry, which provided marble for the National Gallery of Art, or enjoy the scenic beauty of the Proctorsville Gulf. Singleton's General Store in Proctorsville is also a popular stop for cyclists.
Yes, many of the road cycling routes around Proctorsville are designed as loops, allowing you to start and end in the same location. Examples include the Roadbike loop from Ludlow and the Roadbike loop from Cavendish, offering convenient circular journeys.
The region is particularly beautiful during the fall foliage season, offering vibrant colors. Spring and summer also provide excellent conditions for cycling, with pleasant temperatures and lush landscapes. It's always a good idea to check local road conditions, especially in early spring or late fall.
Yes, for those looking to cover more ground, routes like the Roadbike loop from Cavendish extend for over 66 km (41 miles). This route provides a substantial ride through varied terrain, perfect for experienced cyclists seeking a longer adventure.
Proctorsville and nearby villages offer charming local spots. Singleton's General Store in Proctorsville is a well-known local staple, perfect for a mid-ride snack or to refuel. You'll also find cafes and pubs in nearby towns like Ludlow and Cavendish.
Elevation gains vary depending on the route. Easier routes, such as the Vermont Route 100 scenic views loop from Ludlow, have around 187 meters (613 feet) of ascent. More challenging routes, like the Roadbike loop from Cavendish, can feature over 770 meters (2,500 feet) of climbing, providing a good workout.
Many routes in the Proctorsville area wind through quiet country roads, offering a peaceful cycling experience away from heavy traffic. Exploring routes that venture slightly off the main thoroughfares can often lead to less crowded and more serene rides through the pastoral landscape.
There are 7 road cycling routes around Proctorsville, offering a range of experiences from easy scenic loops to more challenging rides. These routes have been explored by over 40 road cyclists using komoot.


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