4.6
(18)
477
riders
82
rides
Touring cycling in Windsor County offers diverse terrain across river valleys, rolling hills, and forested landscapes. The region is characterized by scenic waterways like the Connecticut and Ottauquechee Rivers, historic covered bridges, and a blend of rural charm with managed woodlands. To the west, the landscape rises into the Green Mountains, providing elevation changes and mountain views. Cyclists can explore routes that parallel the rivers or ascend hills, providing varied and engaging experiences.
Last updated: June 28, 2026
5.0
(3)
18
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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.

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4.7
(3)
19
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
22
riders
17.7km
01:55
520m
520m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
12
riders
42.2km
02:49
510m
510m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
76.4km
05:04
1,120m
1,120m
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.
5.0
(1)
13
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
riders
68.7km
06:34
1,400m
1,400m
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
Forest Dale is a small community with a church, post office, and historic early-1800s ironworks, the ruins of which can be found on the northeast side of town. The Junction Store & Deli is open 7am-7pm most days if you want to grab a bite before continuing on your ride.
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Extremely hilly, sounds of nature, lot's to see & experience. Downhills are well worth the climbs. You definitely need to have some rides/climbing in your season. Update 7/26/25 Still crazy hilly & and punchy. However, the downhill runs are amazing..😉
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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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Known as Vermont's Grand Canyon, you get a splendid view of the gorge from the road bridge. You can also park up your bike and take the hiking path to explore it further and go for a swim in the summer.
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Brandon Gap is a tall mountain pass in the green mountains on Gap Road. This is a challenging climb in a beautiful area in the green mountains. The Long Trail crosses the road right at the summit of the pass, so be on the lookout for thru-hikers as you ride past!
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Middlebury Gap is a mountain pass in Vermont's Green Mountains and a great, very challenging climb for any rider. It divides two different drainage areas with the Robbins Branch flowing southeast into the White River, and the South Branch into Middlebury River, which into Otter Creek, connecting to Lake Champlain. The Long Trail, a 272-mile hiking route traversing Vermont, runs through here, passing between Worth Mountain and Boyce Mountain. The Breadloaf Wilderness lies to the north, while Middlebury College Snow Bowl and Joseph Battell Wilderness are nearby to the south.
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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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Rochester welcomes visitors with its quintessential New England charm. Nestled amid picturesque mountains, the town offers outdoor adventures, artisan shops, and local eateries. Explore the scenic Green Mountain National Forest, discover charming boutiques, and savor the hospitality of this Vermont gem.
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Windsor County offers a wide selection of touring cycling routes, with over 70 options available on komoot. These routes cater to various preferences, from moderate rides through scenic valleys to more challenging ascents.
The touring cycling routes in Windsor County range from moderate to difficult. You'll find approximately 29 moderate routes, perfect for a relaxed exploration, and 45 difficult routes for those seeking a more challenging ride with significant elevation gains.
While most routes are classified as moderate to difficult, many moderate options are suitable for beginners looking for a scenic ride without extreme challenges. These often follow river valleys or less strenuous terrain. For example, the Taftsville Covered Bridge – Quechee Covered Bridge loop from George Perkins Marsh Boyhood Home is a moderate 18.7-mile route that offers beautiful scenery.
Yes, Windsor County is home to many challenging touring cycling routes, particularly those that venture into the rolling hills and higher elevations. Routes like the Rochester – Brandon Gap loop from Lions Club Picnic Area, spanning over 47 miles with significant climbing, offer a demanding experience for advanced cyclists.
Touring cyclists in Windsor County can expect diverse and picturesque scenery. Routes often follow river valleys like the Ottauquechee and Connecticut Rivers, passing historic covered bridges, charming farms, and sugarhouses. You'll also encounter rolling hills, managed forests, and dramatic natural features such as Quechee Gorge. Many routes offer rewarding views from higher elevations, like those around Mount Ascutney or Mount Tom.
Yes, many touring cycling 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 from Quechee and the Woodstock Middle Covered Bridge – Mount Peg loop from George Perkins Marsh Boyhood Home, which offer varied distances and scenery.
Windsor County's touring cycling routes often pass by or near significant landmarks and natural attractions. You can explore historic covered bridges, such as the Cornish-Windsor Covered Bridge, or visit charming towns like Windsor and Woodstock. Natural highlights include The Pogue, Lake Runnemede, and the dramatic Quechee Gorge. For panoramic views, consider routes near Mount Tom or the Observation Tower on Mount Ascutney.
The best time for touring cycling in Windsor County is generally from late spring through early autumn. During these seasons, the weather is most favorable, and the natural beauty of the region, from lush greenery to vibrant fall foliage, is at its peak. Spring offers blooming landscapes, while autumn provides stunning colors, making for particularly scenic rides.
The touring cycling routes in Windsor County are highly regarded by the komoot community, with an average rating of 4.6 stars from over 10 reviews. Cyclists often praise the region's beautiful river valleys, the charm of its historic covered bridges, and the varied terrain that offers both scenic and challenging experiences. Over 400 touring cyclists have already explored the area using komoot.
Yes, several routes in Windsor County offer views of or pass near beautiful water features. You can find routes that skirt tranquil bodies of water like The Pogue and Lake Runnemede. Additionally, some areas feature scenic spots like the Mill Ponds Waterfall Viewing Spot, providing refreshing stops along your ride.
Absolutely. Windsor County's varied topography means many routes include rewarding viewpoints. For instance, the Carriage Barn Visitor Center – Taftsville Covered Bridge loop from George Perkins Marsh Boyhood Home offers scenic vistas. You can also find specific viewpoints like the West Peak Vista / Glider Area on Mt. Ascutney, which can be incorporated into longer rides for breathtaking panoramas.
Yes, Windsor County is shaped by the Connecticut River, and several touring cycling routes offer scenic rides parallel to its waterways. These routes provide picturesque views of the river, passing through charming rural landscapes with farms and historic structures. The Hanover – Connecticut River loop from Norwich is an excellent example, offering a substantial ride along the river.


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