The best road cycling routes around Windsor
92
riders
14
rides
Road cycling routes around Windsor traverse a landscape characterized by the Connecticut River Valley, offering a mix of flat stretches and rolling hills. The region features historic covered bridges and rural roads that wind through agricultural areas and forested sections. Elevations generally remain moderate, with some routes including climbs towards local peaks.
Best road cycling routes around Windsor
- The most popular road cycling route is Plainfield loop from Cornish, an easy 20.4 miles (32.8 km) trail that takes 1…
Last updated: July 15, 2026
6
riders
32.8km
01:24
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
18
riders
17.3km
01:22
740m
740m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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14
riders
47.0km
02:04
450m
450m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
10
riders
27.0km
01:48
840m
840m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
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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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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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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The road cuts through the Saint-Gaudens Historical National Park. It was once the home of the celebrated sculptor, Augustus Saint-Gaudens. The grounds are peppered with casts of his most famous works. If you have time to return after your ride to look around, it is well worth it. As you ride through, you pass Blow-Me-Down Pond, a beautiful wetland right next to the road.
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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 road cycling routes are available in Windsor?
There are 14 road cycling routes around Windsor, offering a variety of experiences for different skill levels. You'll find 3 easy routes, 10 moderate routes, and 1 challenging route.
Are there easy road cycling routes suitable for beginners in Windsor?
Yes, Windsor offers several easy road cycling routes. A great option for beginners is the Plainfield loop from Cornish, which is an easy 20.4-mile ride through the countryside.
What are some of the longer road cycling routes available in the Windsor area?
For those looking for a longer ride, the Woodstock Middle Covered Bridge – Taftsville Covered Bridge loop from Hartland is a moderate 44.3-mile route. It offers a substantial ride through scenic areas.
Are there challenging road cycling routes for experienced riders?
Yes, for a more challenging experience, consider routes that include significant climbs. The Mt. Ascutney Climb loop from Windsor, for example, is a moderate 16.8-mile trail with a substantial elevation gain, providing a good test for experienced cyclists.
When is the best time of year for road cycling in Windsor?
The best time for road cycling in Windsor is typically from late spring through early autumn (May to October). During these months, the weather is generally mild, and the foliage offers beautiful scenic backdrops, especially in the fall.
What kind of weather should I expect for road cycling in Windsor?
Windsor experiences four distinct seasons. Summers are warm and humid, while spring and autumn offer cooler, more pleasant temperatures. Winters can be cold with snow, making road cycling less ideal due to icy conditions and snow-covered roads.
Are there any circular road cycling routes in Windsor?
Many of the road cycling routes in Windsor are designed as loops, allowing you to start and end in the same location. Examples include the Plainfield loop from Cornish and the Cornish-Windsor Covered Bridge loop from Windsor.
What scenic attractions can I see along the road cycling routes in Windsor?
Road cycling routes in Windsor often feature picturesque views of the Connecticut River Valley, historic covered bridges, and rural landscapes. You might pass by landmarks such as the Cornish-Windsor Covered Bridge or enjoy vistas from areas near Mount Ascutney.
Are there any waterfalls or natural features to explore near the cycling routes?
Yes, some routes are in proximity to natural attractions. For instance, you might find the Little Cascade Falls in the wider Windsor area, which can be a refreshing stop or a point of interest near certain cycling paths.
What do other road cyclists enjoy the most about road cycling in Windsor?
The komoot community frequently praises the varied terrain, from flat river valley stretches to rolling hills, and the charm of the historic covered bridges. The region's rural roads and scenic beauty are often highlighted as key attractions for road cyclists.
Are the road cycling routes in Windsor suitable for families?
Many of the easier, flatter routes, particularly those along the river valleys, can be suitable for families. The Plainfield loop from Cornish is an easy option that could be enjoyed by families looking for a gentle ride.
Where can I find parking for road cycling routes in Windsor?
While specific parking details for each route are not always listed, you can generally find public parking in the town centers of Windsor and Cornish, or at designated trailheads. It's advisable to check local town websites for specific parking regulations and locations.
Most popular routes around Windsor
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