4.5
(18)
443
riders
50
rides
No traffic touring cycling routes in Windsor County traverse a diverse landscape characterized by the Connecticut River, rolling hills, and extensive forests. The region features prominent natural landmarks like Mount Ascutney, offering varied terrain from river valleys to challenging climbs. Historic covered bridges and charming villages are often integrated into the cycling paths. This varied topography provides a range of experiences for touring cyclists.
Last updated: April 25, 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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5.0
(1)
13
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
32.8km
02:55
570m
570m
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.
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Popular around Windsor County
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Traffic-free bike rides in Windsor County
Traffic-free bike rides in Windsor County
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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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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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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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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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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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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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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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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Windsor County offers a wide selection of touring cycling routes designed to minimize traffic, with over 50 options available. These routes range from moderate to difficult, providing diverse experiences for cyclists.
You'll find a diverse range of terrain, from scenic river valleys along the Connecticut River to challenging mountain climbs, particularly around Mount Ascutney. Many routes incorporate rolling hills, offering varied elevation changes and beautiful vistas. You can also find mixed-surface routes that combine paved roads with unpaved country roads and gravel sectors for a more adventurous ride.
Yes, for a relaxed and family-friendly experience, consider the Toonerville Rail-Trail. This 3.2-mile paved path runs along the Black River, a tributary of the Connecticut River, offering scenic views in a traffic-free environment. It's an excellent choice for all ages.
Windsor County is rich in natural beauty and historic sites. You can cycle past several historic covered bridges, such as the Taftsville Covered Bridge, or visit the iconic Quechee Gorge Bridge, often called "Vermont's Grand Canyon." Many routes also offer views of Mount Ascutney and the tranquil waters of The Pogue or Deweys Pond. For a unique stop, consider the Carriage Barn Visitor Center.
Yes, many of the no-traffic touring cycling routes in Windsor County are designed as loops. For example, the Taftsville Covered Bridge – Quechee Covered Bridge loop from George Perkins Marsh Boyhood Home offers a moderate 30 km ride, showcasing two beautiful covered bridges. Another option is the Woodstock Middle Covered Bridge – Mount Peg loop from George Perkins Marsh Boyhood Home, a more challenging 17.7 km route.
The komoot community highly rates the touring cycling experience in Windsor County, with an average score of 4.5 stars. Reviewers often praise the region's quiet country roads, the stunning natural beauty of the rolling hills and river valleys, and the charm of the historic villages and covered bridges. The variety of routes, from gentle paved paths to challenging gravel climbs, is also frequently highlighted.
Yes, Windsor County offers natural beauty including waterfalls. You can explore areas like the Mill Ponds Waterfall Viewing Spot, which is a highlight in the region. While specific no-traffic touring routes might not directly pass every waterfall, many routes are in close proximity to such natural features, allowing for short detours.
Many towns and villages in Windsor County, such as Windsor, Chester, and Woodstock, serve as excellent starting points and offer public parking. Specific state parks like Mount Ascutney State Park or areas near popular attractions like the Quechee Gorge Bridge also provide designated parking facilities, often with easy access to cycling routes.
Absolutely. Many routes are designed to connect charming historic villages like Windsor and Woodstock, which offer amenities such as cafes, restaurants, and shops. For instance, the Taftsville Covered Bridge – Carriage Barn Visitor Center loop from Quechee takes you through scenic areas with potential stops for refreshments. Artisan's Park in Windsor, home to local businesses, is another popular stop for cyclists.
The late spring, summer, and early fall months generally offer the best conditions for touring cycling in Windsor County. Spring brings lush greenery, while summer provides warm weather for exploring. Autumn is particularly popular for its vibrant fall foliage, making for incredibly scenic rides. Always check local weather conditions before heading out.
Yes, experienced touring cyclists will find plenty of challenges. The region features routes with significant elevation gain, particularly around Mount Ascutney. For example, the Taftsville Covered Bridge – Carriage Barn Visitor Center loop from George Perkins Marsh Boyhood Home is a difficult 60 km route with over 1200 meters of elevation gain, offering a substantial workout on quiet roads.


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