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Routes
Cycling routes
United States
Vermont
Windsor County

Windsor

The best cycling routes around Windsor

4.0

(2)

32

riders

9

rides

Touring cycling routes around Windsor are characterized by a blend of historical landscapes, expansive royal parks, and serene riverside paths. The region offers generally flat terrain, particularly around Windsor Castle and along the River Thames, making it accessible for various cycling abilities. Cyclists can explore designated paths within Windsor Great Park, which features ancient oak trees and views of the castle. The area also includes picturesque routes along the River Thames and the Jubilee River, providing tranquil environments for cycling.

Last updated: May 5, 2026

#1.

Plainfield loop from Cornish

32.8km

01:59

290m

290m

Enjoy a moderate 20.4-mile touring cycling loop from Cornish, featuring the Cornish-Windsor Covered Bridge and scenic New Hampshire views.

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Moderate

10

riders

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

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

Hard

4.0

(1)

5

riders

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

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

Natalie
January 29, 2024, Billings Farm & Museum

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 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 during your ride to look around, it is well worth it. Take the Saint-Gaudens Road to the northwest. If you're just riding through, you pass Blow-Me-Down Pond, a beautiful wetland right next to the road.

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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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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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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 touring 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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Natalie
December 13, 2023, Westerly Bridge

Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.

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The Carriage Barn Visitor Center is open from 10am-5pm, Memorial Day weekend until October 31. The building was constructed on the foundation of a stable that the Billings Family originally erected in 1895 to house their horses and carriages. The main floor of this Visitor Center houses an exhibit Conservation Stewardship, a bookstore and a reading area, and restrooms. Park Rangers are there daily to answer any questions you might have. The Carriage Barn Visitor Center is a great place to stop by before exploring the Marsh-Billings-Rockefeller National Historical Park.

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Frequently Asked Questions

How many touring cycling routes are available around Windsor?

There are 9 touring cycling routes available around Windsor. These routes offer a diverse range of experiences, from moderate rides through varied landscapes to more challenging, extensive paths through scenic countryside.

What are the general difficulty levels of touring cycling routes in Windsor?

The touring cycling routes in Windsor cater to a range of abilities. You'll find 4 moderate routes and 5 difficult routes. The terrain around Windsor Castle and along the River Thames is generally flat, making it accessible, but some routes extend into more challenging areas.

What kind of landscapes can I expect to see while cycling around Windsor?

While cycling around Windsor, you can expect a rich blend of historical landscapes, expansive royal parks, and serene riverside paths. Highlights include the ancient oak trees and iconic Long Walk in Windsor Great Park, picturesque sections along the River Thames and Jubilee River, and the natural beauty of areas like Burnham Beeches and Dorney Lake.

Are there any specific areas known for scenic views or natural beauty?

Absolutely. Windsor Great Park offers stunning views, including glimpses of Windsor Castle from the Long Walk. The Jubilee River is noted for its peaceful environment and lush greenery. For specific viewpoints, consider visiting the West Peak Vista / Glider Area on Mt. Ascutney, which offers expansive vistas.

Are there family-friendly touring cycling routes in Windsor?

Yes, Windsor's relatively flat terrain, particularly around Windsor Castle and along designated paths in Windsor Great Park, makes it suitable for families. While specific 'easy' routes aren't listed in the top selections, many sections of the National Cycle Route 4 are accessible and enjoyable for various ages. Always check the route details for elevation and distance to ensure it suits your family's ability.

Are there circular touring cycling routes available?

Yes, many of the touring cycling routes around Windsor are circular, allowing you to start and end at the same point. Examples include the Plainfield loop from Cornish, the Woodstock Middle Covered Bridge – Silver Hill loop from Windsor Trail, and the Bowers Covered Bridge loop from West Windsor.

Where can I park my bike or car when cycling in Windsor?

For cyclists, secure cycle parking facilities are available, such as at the Windsor Leisure Centre. If arriving by car, various car parks are available in and around Windsor, though it's always advisable to check local council websites for the most current information on parking availability and charges. For more information on getting around Windsor, you can visit windsor.gov.uk.

What historical landmarks or attractions can I visit while cycling in Windsor?

Windsor is rich in history. You can enjoy views of Windsor Castle from routes within Windsor Great Park. The historic town of Eton, home to Eton College, is often included in routes. Other significant sites include Runnymede, where the Magna Carta was signed, and the historic Cornish-Windsor Covered Bridge. Dorney Court is another historic country house that can be part of your cycling tour.

Are there any waterfalls or unique natural features to see?

Yes, for those interested in natural features, the Little Cascade Falls is a notable highlight in the area. Additionally, the serene Jubilee River is known for its peaceful environment and opportunities for birdwatching, offering a unique natural experience.

Can you recommend a challenging touring cycling route?

For a challenging touring cycling experience, consider the Woodstock Middle Covered Bridge – Silver Hill loop from Windsor Trail. This extensive route covers 63.3 miles (101.9 km) and features significant elevation changes, providing a demanding ride through scenic countryside.

What's a shorter touring cycling route for a quicker ride?

If you're looking for a shorter ride, the Bowers Covered Bridge loop from West Windsor is an excellent choice. This route is 6.4 miles (10.3 km) long and can typically be completed in about 49 minutes, leading you through pleasant rural settings.

What do other touring cyclists say about the routes in Windsor?

The touring cycling routes in Windsor are highly rated by the komoot community, with an average score of 4.0 stars from 2 reviews. Cyclists often praise the blend of historical sights, royal parks, and tranquil riverside paths, noting the accessibility of the generally flat terrain around key attractions.

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