5.0
(12)
224
riders
65
rides
Gravel biking in Windsor County, Vermont, offers diverse terrain characterized by rolling hills, dense forests, and picturesque river valleys. The region features an extensive network of gravel roads, winding past natural landmarks like Quechee Gorge and Mount Ascutney. These routes often incorporate historical elements such as covered bridges, providing varied landscapes for gravel cyclists.
Last updated: May 16, 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.
7
riders
38.2km
02:31
700m
700m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
6
riders
28.0km
01:50
490m
490m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Windsor County
Gravel biking around Wilder

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Gravel biking around South Woodstock
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Gravel biking around Quechee
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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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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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A lovely old cemetery surrounded by a stone wall. Jump off the bike to take a closer look on foot.
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A lovely quiet lane winding through the trees. Keep your eyes peeled for the varied bird species that inhabit the trees canopy.
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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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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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This area is undeveloped, featuring a lush second-growth forest with miles of trails, ponds, and available camping areas. There are also several viewpoints that offer a wonderful view of the Vermont countryside.
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Windsor County offers over 60 gravel biking routes, catering to various skill levels. The majority are challenging, with 46 difficult routes, 16 moderate, and 1 easy option.
You'll find diverse terrain, from rolling hills and dense forests to picturesque river valleys. The region is known for its extensive network of gravel roads, often winding past natural landmarks and historical elements like covered bridges.
While many routes are challenging, the area around Brownsville offers options for different skill levels, including family-friendly trails with lower elevation gain and dirt road options. For a moderate ride, consider the Taftsville Covered Bridge – Quechee Covered Bridge loop from Quechee, which is 26.7 km long with less elevation.
Many routes incorporate historical elements like covered bridges, such as the Taftsville Covered Bridge and the Quechee Gorge Bridge. You might also pass by natural features like Quechee Gorge or the serene The Pogue in Woodstock.
Yes, many routes are designed as loops. For example, the challenging Quechee Covered Bridge loop from Quechee is a 31.2 km circular route, and the Silver Lake – Silver Lake loop from Silver Lake State Park offers a 38.2 km ride around the lake.
The gravel biking routes in Windsor County are highly rated by the komoot community, with an average score of 4.8 stars from over 10 reviews. Users often praise the varied terrain, picturesque scenery, and the blend of challenging climbs and rewarding descents.
For a longer ride, consider the challenging Taftsville Covered Bridge – Woodstock Middle Covered Bridge loop from Windsor Trail, which spans 72.9 km and takes approximately 7 hours 35 minutes to complete. Another substantial option is the Billings Farm & Museum – Carriage Barn Visitor Center loop from George Perkins Marsh Boyhood Home, covering 62.4 km.
Many routes start from towns or parks where parking is available. For instance, the Silver Lake loop starts from Silver Lake State Park, which typically offers parking facilities. Routes originating from places like Quechee or West Windsor also usually have accessible starting points.
Yes, you can find routes that include scenic water bodies. The Crescent Lake – CCC Pond loop from Wilder is a 46 km challenging route that takes you past both Crescent Lake and CCC Pond.
Most gravel bike trails in Windsor County are considered difficult, with 46 out of 63 routes falling into this category. These routes often feature significant elevation gains and varied terrain, offering a good challenge for experienced riders.
While the majority are difficult, there is one easy route available, and 16 moderate options. The Taftsville Covered Bridge – Quechee Covered Bridge loop from Quechee is a moderate 26.7 km ride with less climbing, making it a good choice for those looking for a less strenuous experience.
While specific komoot routes listed don't directly ascend Mount Ascutney, the area around Mount Ascutney and the Connecticut River is rich with cycling opportunities. The mountain itself offers over 35 miles of mountain biking trails within Mt. Ascutney State Park, and a paved parkway leads to scenic overlooks.


Check out more Gravel rides throughout Windsor County below and find the perfect route in your destination.
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