The best gravel rides in Windsor County
5.0
(15)
261
riders
72
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.
Best gravel bike trails in Windsor County
- The most popular gravel bike trail is Taftsville Covered Bridge – Woodstock Middle Covered Bridge loop from Windsor Trail, a 45.3 miles (72.9 km) trail that takes 7 hours 35 minutes to complete, connecting two notable covered bridges.
- Another top favourite among local gravel bikers is Taftsville Covered Bridge – Carriage Barn Visitor Center loop from George Perkins Marsh Boyhood Home, a difficult 37.4 miles (60.2 km) path, offering significant elevation gain through varied terrain.
- Local gravel bikers also love the Carriage Barn Visitor Center – Woodstock Middle Covered Bridge loop from George Perkins Marsh Boyhood Home, a 19.6 miles (31.5 km) trail leading through forested areas and past historical sites, often completed in about 2 hours 16 minutes.
- Gravel biking in Windsor County is defined by rolling hills, river valleys, and extensive gravel roads, often passing by covered bridges and old sugar shacks. The network offers options for various fitness levels, from challenging climbs to more moderate rides.
- The routes in Windsor County are highly rated by the komoot community with an average score of 4.8 stars from more than 10 reviews. More than 200 gravel bikers have used komoot to explore Windsor County's varied terrain.
Last updated: July 25, 2026
5.0
(1)
9
riders
60.3km
04:35
1,200m
1,200m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
5
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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8
riders
The Carriage Barn Visitor Center – Woodstock Middle Covered Bridge loop from Woodstock offers a true taste of Vermont's gravel biking scene. You'll navigate an extensive network of backcountry gravel roads, winding through picturesque New England scenery with rolling hills, working farms, and views of rushing brooks. The route's highlight is the historic Woodstock Middle Covered Bridge, a unique structure spanning the Ottauquechee River, all set against a backdrop of distant Green Mountains.
This difficult 19.6-mile (31.5 km) gravel biking route involves a substantial 2155 feet (657 metres) of elevation gain, typically taking around 2 hours and 16 minutes to complete. It's best suited for riders with good fitness who are comfortable with varied terrain, including potentially challenging Class IV sections. The starting point at the Carriage Barn Visitor Center, located within the Marsh-Billings-Rockefeller National Historical Park, provides convenient access and amenities.
What makes this loop stand out among popular gravel biking trails in Woodstock, Vermont, is its blend of accessible moderate difficulty with quintessential Vermont scenery. The region is a global destination for gravel cycling due to its varied terrain, scenic vistas, and low-traffic backcountry roads. This particular route is a favorite among local gravel bikers, offering a rewarding experience that showcases the area's natural beauty and historic landmarks.
5.0
(1)
7
riders
31.2km
02:14
640m
650m
The Quechee Covered Bridge loop from Quechee offers a challenging and scenic gravel biking adventure through Vermont's picturesque landscape. You'll navigate varied terrain, from hard-packed dirt to sections with loose gravel and even some sandy stretches, all while enjoying views of the Ottauquechee River and the dramatic Quechee Gorge. The route also takes you past the historic Quechee Covered Bridge, providing a classic New England experience.
This difficult 19.4-mile (31.2 km) route involves a substantial 2115 feet (644 metres) of elevation gain, typically taking around 2 hours and 14 minutes to complete. Parking is available in Quechee, but consider an early start, especially during peak seasons, to secure a spot. Be mindful of the ongoing rehabilitation of the Quechee Gorge Bridge, which could impact local traffic, though pedestrian access remains open.
This trail is a fantastic choice for experienced gravel bikers looking for a rewarding ride with plenty of natural beauty and a touch of history. The region is known for its stunning fall foliage, making autumn an especially popular time to explore the Quechee gravel biking routes. You'll find amenities like restrooms and a visitor center near the Quechee Gorge, perfect for a mid-ride break.
9
riders
46.0km
03:15
880m
880m
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)
5
riders
28.8km
01:58
580m
580m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
26.5km
01:56
640m
640m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
78.3km
05:45
1,680m
1,680m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
23.7km
01:44
570m
570m
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
Gravel biking around Norwich
Gravel biking around North Hartland
Gravel biking around Windsor
Gravel biking around Quechee
Gravel biking around Hartland
Gravel biking around Woodstock Village
Gravel biking in North Hartland Dam Recreation Area
Gravel biking around South Royalton
Gravel biking around White River Junction
Other adventures in Windsor County
Tips from the Community
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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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 is a lovely run around the shores of Lake Runnemede along a relatively flat and grassy footpath that's right up on the water's edge, creating lovely scenes as you make your way around.
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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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Frequently Asked Questions
How many gravel bike trails are available in Windsor County?
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.
What kind of terrain can I expect on gravel bike trails in Windsor County?
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.
Are there any family-friendly gravel biking routes in Windsor County?
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.
What are some notable landmarks or attractions I can see along the gravel bike trails?
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.
Are there any circular gravel bike routes in Windsor County?
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.
What do other gravel bikers say about the trails in Windsor County?
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.
Are there any long-distance gravel biking options in the area?
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.
Where can I find parking for gravel biking trailheads?
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.
Are there any routes that pass by lakes or ponds?
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.
What is the difficulty level of most gravel bike trails in Windsor County?
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.
Can I find routes that are less strenuous for beginners?
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.
Are there any routes that explore the area around Mount Ascutney?
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.
Most popular routes in Windsor County
Most popular attractions in Windsor County
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