4.8
(12)
180
riders
34
rides
Touring cycling routes around Woodstock Village traverse a landscape characterized by the scenic Green Mountains and the meandering Ottauquechee River. The region features prominent hills like Mt. Tom and Mt. Peg, offering extensive trail systems. Rolling hills, working farms, and historic covered bridges contribute to the diverse terrain. This area provides varied cycling experiences across its network of backcountry roads.
Last updated: May 21, 2026
5.0
(3)
17
riders
30.0km
02:03
180m
180m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
21
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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11
riders
68.7km
06:34
1,400m
1,400m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
60.3km
05:56
1,200m
1,200m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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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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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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Named after A.G. Dewey, who owned a mill there 1869-1960s. , explore old wool mill ruins and look out for beautiful yellow-rumped warblers, black-throated warbler Northern goshawks, bald and golden eagles, red-tailed and red-shouldered hawks, ospreys, blue jays, and mourning doves.
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Woodstock Village offers a diverse network of touring cycling routes, ranging from leisurely village rides to more challenging paths through rolling hills and past historic covered bridges. The landscape features the scenic Green Mountains and the meandering Ottauquechee River, providing varied terrain for all skill levels. You'll find routes that showcase working farms, picturesque vistas, and iconic landmarks.
Yes, Woodstock Village caters to all skill levels. While specific 'easy' touring routes aren't explicitly listed in the top routes, the area's extensive network includes paths suitable for leisurely rides. For families, the village itself and flatter sections along the Ottauquechee River Trail offer pleasant cycling experiences. The Woodstock Inn & Resort also provides complimentary cruiser bikes for exploring the village at a relaxed pace.
For those seeking a challenge, routes like the Woodstock Middle Covered Bridge – Mount Peg loop from George Perkins Marsh Boyhood Home offer significant ascents, including climbs to Mt. Peg with rewarding views. Another difficult option is the Carriage Barn Visitor Center – Taftsville Covered Bridge loop from George Perkins Marsh Boyhood Home, which covers over 21 miles with substantial elevation gain through rolling hills.
Woodstock is well-equipped for bike rentals. Woodstock Wheels offers self-guided e-bike tours with pre-mapped routes. Mountain bike rentals are available at the Woodstock Inn Activity Center, and the Woodstock Inn & Resort also provides complimentary cruiser bikes for guests to explore the village.
Cycling routes around Woodstock Village often pass by significant natural and historical landmarks. You can expect to see picturesque covered bridges, such as the Taftsville Covered Bridge, and enjoy views of the Ottauquechee River. Many routes offer glimpses of the scenic Green Mountains and prominent peaks like Mount Tom. The Carriage Barn Visitor Center is also a common starting point or landmark on several tours.
Yes, many of the touring cycling routes in Woodstock Village are designed as loops, allowing you to start and end at the same point. Examples include the popular Taftsville Covered Bridge – Quechee Covered Bridge loop from George Perkins Marsh Boyhood Home, and the Woodstock Middle Covered Bridge – Carriage Barn Visitor Center loop from George Perkins Marsh Boyhood Home.
The Woodstock area is beautiful throughout the warmer months. Spring and especially autumn offer stunning scenery with vibrant foliage. The region hosts numerous organized rides and festivals, particularly during the cycling season. While winter fat biking is an option, the primary touring cycling season typically runs from spring through fall, when trails are clear and weather is favorable.
While Woodstock Village is a premier destination for cycling, specific public transportation options directly serving trailheads for cyclists might be limited. It's generally recommended to plan your route and parking in advance, especially if you're bringing your own bike. Many routes start from central locations or visitor centers, which may have better accessibility.
Parking availability varies by trailhead. For routes starting near the George Perkins Marsh Boyhood Home or the Carriage Barn Visitor Center, you may find designated parking. For specific trail networks like Mt. Peg Trails or the Woodstock Aqueduct Trails, it's advisable to check local resources for parking information, as options can range from dedicated lots to roadside parking.
Many outdoor areas in Woodstock Village, including some trails, are dog-friendly, but leash policies and specific trail restrictions may apply. It's always best to check local signage or official park websites for the most up-to-date information regarding pets on trails, especially within areas like the Marsh-Billings-Rockefeller National Historical Park.
The touring cycling routes in Woodstock Village are highly rated by the komoot community, with an average score of 4.75 stars from over 10 reviews. Cyclists often praise the diverse terrain, the beauty of the Green Mountains and Ottauquechee River, and the charm of the historic covered bridges and working farms encountered along the way.
Woodstock Village itself is known for its charming atmosphere, with tree-lined streets and a vibrant village green. You'll find various cafes, restaurants, and pubs within the village center, making it easy to refuel before or after your ride. Many routes pass close to or through the village, offering convenient access to amenities.


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