74
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Road cycling routes around West Woodstock, Vermont, navigate a landscape characterized by rolling hills, the Ottauquechee River, and the foothills of the Green Mountains. The area features varied elevation, offering both gentler rides and more challenging ascents. Historic covered bridges and scenic roads contribute to the region's distinct character. This terrain provides diverse road cycling experiences for different fitness levels.
Last updated: July 2, 2026
10
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
54.9km
03:21
820m
820m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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7
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
9
riders
42.2km
02:47
450m
450m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Deweys Mill Dam is a small dam constructed in 1989. It is built on the Ottauquechee River and created Deweys Pond. There is a viewing platform near the dam which gives you a good view of the small cascada created by the dam.
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Known as Vermont's Grand Canyon, you get a splendid view of the gorge from the road bridge. You can also park up your bike and take the hiking path to explore it further and go for a swim in the summer.
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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 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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Known as Vermont's Grand Canyon, you get a splendid view of the gorge from the road bridge. You can also park up your bike and take the hiking path to explore it further and go for a swim in the summer.
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On the north side of the river there is a viewing spot where you can have a closer look at the Mill ponds and old dam waterfall. In the winter, the water freezes; a spectacular sight.
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Built recently in 2012, Hurricane Irene had damaged the previous structure so badly that it didn't reach the river bank on either side. It has been sympathetically redesigned to complement the other covered bridges in the area.
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Taftsville Covered Bridge was opened in 1836 and is very well maintained. You can also walk down onto the river bank to get a lovely view of the river crossing from below. There are information boards which provide further information about the wooden bridge's history.
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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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There are 7 road cycling routes around West Woodstock documented on komoot, offering a variety of experiences for different skill levels. These routes navigate the region's rolling hills, the Ottauquechee River, and historic covered bridges.
The fall foliage season is particularly vibrant and popular for road cycling in West Woodstock, offering stunning views. However, the region provides excellent cycling opportunities throughout the warmer months, from spring to early autumn, with varied terrain and scenic routes.
Yes, while many routes feature varied elevation, there are options suitable for different fitness levels. The area offers routes with gentler climbs and steady descents. For example, the Middle Covered Bridge – Silver Lake loop from Lincoln Covered Bridge is a moderate option that passes by scenic Silver Lake.
West Woodstock, nestled within the Green Mountains, offers routes with significant elevation gains for those seeking a challenge. The varied terrain allows for demanding ascents and rewarding descents. Routes like the Taftsville Covered Bridge – Lincoln Covered Bridge loop from George Perkins Marsh Boyhood Home, at over 100 km with substantial elevation, provide a good test for advanced cyclists.
Road cycling routes in West Woodstock frequently pass by working farms, historic covered bridges, and offer stunning views of Mt. Ascutney and the Green Mountains. You can expect to see landmarks like the Taftsville Covered Bridge and the Woodstock Middle Covered Bridge, as well as the tranquil The Pogue.
Yes, many of the road cycling routes in West Woodstock are designed as loops, allowing you to start and end at the same point. Examples include the Vermont Route 100 scenic views – Lincoln Covered Bridge loop from Woodstock and the Lake Runnemede – Martin's Mill Covered Bridge loop from Breeze Hill.
While specific cafe stops are not detailed for every route, the region's cycling-friendly atmosphere and connectivity to nearby towns like Barnard, Pomfret, and Hartland suggest opportunities for refreshments. Local establishments like the Barnard General Store are popular stops for cyclists.
Parking is generally available in and around West Woodstock, particularly at trailheads or designated public parking areas. For routes starting from specific points like the George Perkins Marsh Boyhood Home, parking facilities are typically accessible.
While the focus is on road cycling, many areas around West Woodstock are dog-friendly, especially on trails and in parks. However, it's always best to check specific regulations for each route or park, especially within the Marsh-Billings-Rockefeller National Historical Park, to ensure dogs are permitted on paved roads or paths you plan to cycle.
Generally, no specific permits are required for road cycling on public roads in West Woodstock. However, if your route takes you through specific parks or private lands, it's advisable to check their individual regulations. For example, the Marsh-Billings-Rockefeller National Historical Park has a network of trails, and while roads around it are accessible, specific rules may apply within the park itself.
Road cycling in West Woodstock is unique due to its blend of quintessential New England charm, varied terrain from rolling hills to challenging ascents, and picturesque scenery. Cyclists can enjoy historic covered bridges, the scenic Ottauquechee River, and stunning views of the Green Mountains, especially vibrant during fall foliage. The area offers a rich cultural and natural backdrop for every ride.
For those looking for longer rides, West Woodstock offers several extensive routes. The Vermont Route 100 scenic views – Lincoln Covered Bridge loop from Woodstock is over 100 km, and the Taftsville Covered Bridge – Lincoln Covered Bridge loop from George Perkins Marsh Boyhood Home is also over 100 km, providing significant distance and elevation.


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