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Routes
Gravel rides
United States
Vermont
Windsor County

Windsor

The best gravel rides around Windsor

5.0

(2)

38

riders

12

rides

Gravel biking around Windsor offers a diverse landscape, characterized by rolling hills, river valleys, and wooded areas. The region features a mix of unpaved roads, forest tracks, and multi-use trails suitable for gravel bikes. These routes often traverse scenic countryside, providing varied terrain for different skill levels.

Best gravel bike trails around Windsor

  • 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…

Last updated: May 15, 2026

5.0

(1)

6

riders

#1.

Taftsville Covered Bridge – Woodstock Middle Covered Bridge loop from Windsor

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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Hard

5.0

(1)

6

riders

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

2

riders

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around Windsor

Hiking around Windsor

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Tips from the Community

mtm05005
February 26, 2024, Lake Runnemede

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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Alex
January 29, 2024, Sheep Cemetery

A lovely old cemetery surrounded by a stone wall. Jump off the bike to take a closer look on foot.

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Alex
January 29, 2024, Lovers Lane

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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Grace Mulligan
December 22, 2023, Lake Runnemede

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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Taftsville Covered Bridge was opened in 1836 and is very well maintained. You can also walk down onto the river bank to get a lovely view of the river crossing from below. There are information boards which provide further information about the wooden bridge's history.

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Frequently Asked Questions

How many gravel bike trails are available around Windsor?

There are over 10 gravel bike trails documented in the Windsor area, offering a variety of experiences for different skill levels. These routes are highly rated by the komoot community, with an average score of 5.0 stars.

What kind of terrain can I expect on gravel bike trails in Windsor?

Gravel biking around Windsor is characterized by rolling hills, river valleys, and wooded areas. You'll encounter a mix of unpaved roads, forest tracks, and multi-use trails, providing varied terrain suitable for gravel bikes. Routes often traverse scenic countryside, including challenging climbs through wooded areas.

Are there any easy gravel bike routes for beginners in Windsor?

Yes, there are routes suitable for beginners. For example, the Bowers Covered Bridge loop from West Windsor is an easy 10.4 km path that takes approximately 54 minutes to complete, offering a gentle introduction to the region's gravel roads.

What are some challenging long-distance gravel routes in the Windsor area?

For those seeking a challenge, the Taftsville Covered Bridge – Woodstock Middle Covered Bridge loop from Windsor Trail is a demanding 72.9 km route with significant elevation gain, typically taking over 7 hours to complete. Another difficult option is the Gravel loop from West Windsor, a 28.0 km path exploring the local countryside.

Are there any circular gravel bike routes around Windsor?

Yes, many of the gravel routes in Windsor are designed as loops. Popular circular options include the Gravel loop from Windsor, a 19.4 km trail through rural landscapes, and the Gravel loop from Verdun Hill, a 23.7 km route with notable elevation changes.

What natural attractions or landmarks can I see along the gravel trails?

While exploring the gravel trails around Windsor, you can discover several natural and historical landmarks. Highlights include the Little Cascade Falls, the historic Cornish-Windsor Covered Bridge, and scenic viewpoints like the West Peak Vista / Glider Area on Mt. Ascutney. You might also pass by tranquil spots like Lake Runnemede.

Are there any waterfalls accessible from the gravel bike routes?

Yes, the Little Cascade Falls is a notable waterfall in the region that can be accessed or viewed from routes in the Windsor area, offering a picturesque stop during your ride.

What is the best time of year for gravel biking in Windsor?

The best time for gravel biking in Windsor generally spans from spring through fall, when the weather is mild and the trails are dry. The region's wooded areas offer beautiful foliage in autumn, making it a particularly scenic time to ride. Winter riding can be challenging due to snow and ice, especially on unpaved roads and trails.

Where can I find bike rentals or bike shops in the Windsor area?

While specific bike rental shops are not detailed in the guide data, it's recommended to check local directories or perform a quick online search for 'bike rental Windsor, Vermont' or 'bike shops Windsor, Vermont' to find current options for rentals and repairs in the immediate area.

Are there any family-friendly gravel biking options in Windsor?

Many of the easier and moderate gravel routes, especially those with less elevation gain and shorter distances, can be suitable for families. The region's network of trails offers options for different ability levels, so look for routes marked as 'easy' or 'moderate' to find suitable paths for a family outing.

What do other gravel bikers enjoy most about the trails in Windsor?

The gravel trails in Windsor are highly rated by the komoot community, with an average score of 5.0 stars. Riders often praise the diverse landscape, including rolling hills and river valleys, and the mix of unpaved roads and forest tracks that provide varied and engaging terrain. The scenic countryside and challenging climbs are frequently highlighted as enjoyable aspects.

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