5.0
(12)
217
riders
52
rides
No traffic gravel bike trails in Windsor County, Vermont, traverse a landscape characterized by the Green Mountains to the west and the Connecticut River Valley to the east. The region features an extensive network of backcountry roads, offering varied terrain from challenging climbs to quiet country routes. Riders encounter forested peaks, numerous rivers, and historic covered bridges, making it a notable destination for gravel biking.
Last updated: April 25, 2026
5.0
(1)
7
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
6
riders
79.5km
05:49
1,700m
1,700m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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7
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
6
riders
31.2km
02:14
640m
640m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
46.0km
03:15
880m
880m
Hard gravel 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
This 20-acre lake has easy access from Downer Road. It is surrounded by the Downer State Forest, offering views to Tyler Mountain. The Crescent Lake is a site for the LoonWatch annual survey, which accepts volunteers.
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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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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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Lake Runnemede is a great place for a break during a long ride. The large body of water is home to many species of birds and fish. The water is visible from the road, so if you don't have time to stop, you can still get a great view as you ride by.
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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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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.
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Windsor County offers over 50 dedicated no-traffic gravel bike trails, providing a wide range of options for cyclists looking to explore the region's scenic backcountry roads away from vehicles. These routes are primarily moderate to difficult, ensuring a challenging and rewarding experience.
The best time for gravel biking in Windsor County is typically from late spring through fall. During these seasons, the weather is generally pleasant, and the extensive network of backcountry roads, often lauded as the 'Gravel Road Capital of the Northeast,' is in prime condition. Fall offers stunning foliage views, making it a particularly popular time.
While many of the gravel routes in Windsor County are rated moderate to difficult due to elevation changes, the region also offers some gentler options. For a truly traffic-free and paved experience suitable for families, consider the Toonerville Trail, a 3.2-mile rail trail between Springfield and the Connecticut River. For gravel, look for routes with less elevation gain, though specific 'easy' gravel routes are less common in the more challenging network.
You can expect diverse and picturesque scenery. Routes often traverse quiet, tree-lined country roads, pass through charming New England villages, and offer views of working farms, historic covered bridges, and stunning vistas of the Green Mountains and Mount Ascutney. The Connecticut River Valley also provides rich farmland views along its eastern border.
Yes, many routes pass by or near significant landmarks. You might encounter historic covered bridges, such as those near Brownsville or the Bartonsville Covered Bridge on the Williams River. Other attractions include Observation Tower on Mount Ascutney, Mount Tom, and various lakes like The Pogue or Lake Runnemede. Some trails also offer views of the Mill Ponds Waterfall Viewing Spot.
Most of the no-traffic gravel bike trails in Windsor County are rated as moderate to difficult. This is due to significant climbing and varied terrain, including some 'Class IV' forest roads that can be rougher. Riders should be prepared for elevation changes and potentially challenging surfaces, especially on routes like the 'Dirty Around Mount Ascutney' which is recommended for bikes with 35mm or lower tires.
Yes, many of the gravel routes in Windsor County are designed as loops, allowing you to start and end at the same point. Examples include the Taftsville Covered Bridge – Carriage Barn Visitor Center loop or the Quechee Covered Bridge loop. These circular routes are popular for exploring the diverse landscapes and historic sites of the region.
Parking is often available in or near the charming New England villages that serve as common starting points for gravel rides, such as Brownsville, Chester, Windsor, and Woodstock. Mount Ascutney State Park also offers day-use parking. Always check local regulations and signage for specific parking instructions at trailheads.
The komoot community highly rates the gravel biking experience in Windsor County, with an average score of 4.95 stars. Reviewers often praise the extensive network of quiet, low-traffic backcountry roads, the stunning New England scenery, and the challenging yet rewarding climbs and descents. The presence of historic covered bridges and picturesque villages also adds to the appeal.
Yes, Windsor County is known for its historic covered bridges. Routes like the Taftsville Covered Bridge – Carriage Barn Visitor Center loop and the Taftsville Covered Bridge – Woodstock Middle Covered Bridge loop specifically feature these iconic structures. The Williams River Loop also crosses the Bartonsville Covered Bridge, offering a scenic ride through history.
Absolutely. Mount Ascutney is a prominent landmark in the region, and many gravel routes offer views of its majestic presence. Options like the 'Dirty Around Mount Ascutney' provide mixed-surface riding around its base, and you can also find routes that lead to viewpoints such as the West Peak Vista / Glider Area on Mt. Ascutney.


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