4.6
(36)
2,217
riders
110
rides
Road cycling in Windsor County, Vermont, offers diverse terrain characterized by river valleys, forested hills, and rural roads. The region features a network of routes that navigate past historic covered bridges and along the Connecticut River. Cyclists encounter varied elevation profiles, from rolling hills to more challenging ascents, providing options for different fitness levels. The landscape includes scenic views of bucolic farms and mountain vistas.
Last updated: July 7, 2026
10
riders
66.3km
02:55
620m
620m
Cycle the moderate 41.2-mile Lake Morey from Norwich via Child's Pond loop, enjoying scenic lake views and fall foliage.
3.0
(1)
53
riders
101km
04:29
1,010m
1,010m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
38
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
22
riders
52.9km
02:54
680m
680m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
18
riders
29.2km
01:20
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
46.3km
02:10
540m
540m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
18
riders
17.3km
01:22
740m
740m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
15
riders
28.9km
01:16
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
14
riders
47.0km
02:04
450m
450m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Windsor County

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Climbing Mount Ascutney offers an intense, lung-busting experience as you tackle one of the steepest paved mountain ascents in the United States, winding up through Vermont's forested state park. Prepare for an immediate and unrelenting challenge over approximately 3.7 miles, gaining around 2,300 ft to reach the upper parking lot near 2,900 ft elevation. You'll battle an average gradient of a brutal 11-12%, featuring sustained pitches significantly exceeding 15% and reportedly hitting 20% or more, offering almost no recovery.
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The Thetford Center Covered Bridge is a beautiful historically covered bridge. It carries Tucker Hill Road across the Ompompanoosuc River. It is a fine and very rare example of the Haupt patent truss system.
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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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Woodward Reservoir in Plymouth, Vermont, offers a calm setting for cyclists. With its quiet reservoir and rural surroundings, riders can take a leisurely break. The reservoir's laid-back atmosphere and practical amenities, like picnic areas, provide a straightforward spot for cyclists to relax amidst Vermont's natural scenery.
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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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Windsor County offers a wide selection of road cycling routes, with over 100 options available on komoot. These routes cater to various skill levels, including 9 easy, 64 moderate, and 30 difficult trails, ensuring there's a ride for every cyclist.
You'll find diverse terrain in Windsor County, characterized by scenic river valleys, forested hills, and idyllic rural roads. Routes feature varied elevation profiles, from gentle rolling hills to more challenging ascents, often on lightly traveled country roads. Some routes may also include a mix of paved and unpaved sections, offering a true Vermont cycling experience.
Yes, Windsor County is famous for its historic covered bridges, and several road cycling routes incorporate them. For instance, the Woodstock Middle Covered Bridge – Taftsville Covered Bridge loop from White River Junction is a moderate 35.8-mile ride that showcases these iconic structures. Another popular option is the Cornish-Windsor Covered Bridge loop from Windsor, which takes you past one of the longest covered bridges in the United States.
Many routes in Windsor County provide stunning views. The Lake Morey from Norwich via Child's Pond loop offers beautiful lakeside vistas. For panoramic mountain views, consider routes around Mount Ascutney, such as the Mt. Ascutney Climb loop from Windsor Trail, which provides challenging ascents and rewarding scenery. You can also explore the West Peak Vista / Glider Area on Mt. Ascutney for expansive outlooks.
While many routes are moderate, there are 9 easy routes available in Windsor County. These typically feature less elevation gain and are suitable for a more relaxed pace. Look for routes that follow river valleys or explore flatter rural areas for a family-friendly experience.
The komoot community highly rates road cycling in Windsor County, with an average score of 4.4 stars from over 5 reviews. Cyclists often praise the region's blend of historic landmarks, such as covered bridges, and the serene beauty of its rural roads and river valleys. The varied terrain also allows for rides suitable for different fitness levels.
Yes, Windsor County offers several longer routes for endurance cyclists. For example, the Woodstock Middle Covered Bridge – Billings Farm & Museum loop from Bethel is a challenging 63.6-mile (102.3 km) route. Many other moderate and difficult routes extend over 30 miles, providing ample opportunity for longer rides.
Most of the road cycling routes in Windsor County are designed as loops, allowing you to start and end at the same point. This includes popular options like the Lake Morey from Norwich via Child's Pond loop and the Connecticut River – Hanover loop from White River Junction, making planning convenient.
Beyond the cycling, Windsor County is rich in attractions. You can visit the Lake Runnemede in Windsor, or explore the Mount Tom area. The region is also home to the stunning Quechee Gorge, often called Vermont's 'Little Grand Canyon,' and historic sites like the Old Constitution House in Windsor.
Absolutely. The Connecticut River shapes much of the region's landscape, and you'll find picturesque routes that wind parallel to it. The Connecticut River – Hanover loop from White River Junction is an excellent example, offering scenic riverside cycling past bucolic farms and mountain views.
The best time for road cycling in Windsor County is typically from late spring through early fall (May to October). During these months, the weather is generally pleasant, and the scenery, from lush greenery to vibrant fall foliage, is at its peak. Always check local weather conditions before heading out.
Yes, you can find natural water features. The Mill Ponds Waterfall Viewing Spot is one such highlight. Additionally, lakes like The Pogue and Deweys Pond are located in Windsor County and can be incorporated into your cycling adventures or visited nearby.


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