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Dane County

Windsor

The best cycling routes around Windsor

21

riders

4

rides

Touring cycling around Windsor offers a network of paths suitable for various skill levels. The area features expansive parklands and river paths, providing diverse cycling environments. These routes often follow waterways and traverse relatively flat terrain, making them accessible for many cyclists. The landscape is characterized by open spaces and established trails, ideal for touring.

Best touring cycling routes around Windsor

  • The most popular touring cycling route is Cypress Path – Yahara River loop from East Towne Mall, a…

Last updated: June 28, 2026

9

riders

#1.

Cypress Path – Yahara River loop from East Towne Mall

20.4km

01:10

50m

50m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

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Popular around Windsor

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Road Cycling Routes around Windsor

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Tips from the Community

UrbanExolorer_Mando
July 31, 2025, Pheasant Branch–Hwy 12 Trail Junction

Great Cyclist Junction. Pheasant Branch-Hwy 12 Junction connects North & South Fork to Pheasant Branch Corridor & Hwy 12 path. Local businesses nearby. Great resting point.

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Excellent Cycling hub, connects to multiple paths & areas. Fairly loud due to the highway but excellent scenery. Fix it station on trail & nearby restroom & food options. Costco also nearby.

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Access to Graber Pond/Park+Ride, Greenway Station/Downtown Middleton, Ph. Br. Conservancy/P. V. Golf Course, Capital Ice Arena/Firefighter’s Memorial Park, Dog Park/Penni Klein Park. Excellent bicycle hub.

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Junction for Hwy 12 Path, North/South Fork Trail, Pheasant Branch Creek Corridor. Also connects to South Trail-A. Has Dero Fix-It station. Cute bridge.

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The Capital City State Trail is a 17-mile paved multi-use path open year-round. A state trail pass is required to bike the nine-mile portion of the trail that passes through the Capital Springs E-way south of Madison between Verona Road and Nob Hill near Industrial Drive, but the remainder is free to access.

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very beautiful at the lake shore near Monona Terrace

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David Howells
January 9, 2024, Yahara River

The Yahara River flows 62 miles through Madison's four lakes across Dane County to the Rock River. This is the short stretch between Lake Mendota and Lake Monoana where there are access points available from both lakes and along the river itself at a variety of road crossings. The Yahara Pathway Path runs alongside the river.

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Sue
December 30, 2023, Brittingham Bay

Brittingham Bay is a stunning location that offers many opportunities for outdoor water recreation, including kayaking, paddleboarding, and paddleboating. The small bay is a good place for relaxing on the water, or you can head out to Lake Monona for good views of the capital and more exercise. The bay is surrounded by a beautiful park frequented by many cyclists, walkers and joggers who enjoy its breathtaking views.

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Frequently Asked Questions

What types of cycling routes can I find around Windsor?

Windsor offers a diverse range of touring cycling routes, from expansive parklands to scenic river paths. You'll find designated cycling paths within Windsor Great Park, sections of the National Cycle Route (Network 4), and routes along the River Thames, including parts of the Thames Valley Cycle Route. Many routes feature relatively flat terrain, making them accessible for various skill levels.

Are there easy cycling routes suitable for beginners or families in Windsor?

Yes, Windsor is well-suited for easy cycling. Many routes, particularly within Windsor Great Park and along the Jubilee River path, offer gentle gradients and designated paths. These are ideal for beginners, families, or those seeking a relaxed ride. For example, routes approaching Windsor Castle are often mostly flat and beginner-friendly.

Can I cycle with my dog on the trails around Windsor?

While many outdoor areas in Windsor are dog-friendly, specific rules for cycling with dogs can vary. Within Windsor Great Park, dogs are generally welcome on leads, but it's always best to check specific path regulations. For routes along the Thames Path, ensure your dog is well-behaved and under control, especially in busier sections or near livestock. Always prioritize your dog's safety and the comfort of other path users.

Are there any circular cycling routes in the Windsor area?

Yes, you can find several circular routes around Windsor that allow you to start and end in the same location. Many routes within Windsor Great Park offer loop options, and sections of the Thames Path can be combined with other local roads and paths to create circular tours, allowing you to explore the area's landscapes and attractions without retracing your steps.

What historical sites or attractions can I explore by bike in Windsor?

Windsor is rich in history and offers several attractions accessible by bike. You can cycle past the iconic Windsor Castle, explore the charming town of Eton with its famous college, or visit picturesque riverside towns like Maidenhead, Cookham, and Marlow. The routes often provide scenic views of these landmarks and the historic River Thames.

Is public transport available to access cycling routes in Windsor?

Windsor is well-connected by public transport, making it easy to reach cycling routes. Windsor & Eton Riverside and Windsor & Eton Central stations provide train services, and many bus routes serve the area. Some train services allow bikes, but it's advisable to check with the operator for specific restrictions, especially during peak hours. For more information on getting around Windsor, you can visit the official council website: windsor.gov.uk.

Where can I park my car if I want to cycle in Windsor?

Parking facilities are available in and around Windsor for cyclists. Many car parks are located near popular cycling access points, including those close to Windsor Great Park and the town centre. Secure cycle parking facilities, such as those at Windsor Leisure Centre, are also available to support cycling tourism in the area.

What is the best time of year for touring cycling in Windsor?

Spring and autumn generally offer the most pleasant conditions for touring cycling in Windsor, with milder temperatures and beautiful scenery. Summer can also be excellent, though paths may be busier, especially around popular attractions. Winter cycling is possible, but be prepared for colder, potentially wetter weather and shorter daylight hours.

Are there cafes or pubs along the cycling routes in Windsor?

Yes, many cycling routes around Windsor pass through or near charming towns and villages where you can find cafes, pubs, and restaurants. Along the River Thames, in particular, you'll discover numerous riverside establishments perfect for a refreshment stop. Windsor town centre itself also offers a wide array of options.

Are there any long-distance cycling options from Windsor?

Windsor is part of the National Cycle Network, offering connections for longer rides. National Route 4, also known as the Thames Valley Cycle Route, passes through the area and can be followed for extended distances, such as the scenic route from Reading to Windsor (approximately 31 miles/50km). These routes allow for multi-day tours or longer day trips.

Do I need a permit to cycle in Windsor Great Park?

For general touring cycling on designated paths and roads within Windsor Great Park, a specific permit is typically not required. However, off-road cycling is generally restricted to specific areas like Swinley Forest, which is part of the Windsor Estate and has dedicated mountain biking trails that may have their own access rules or fees. Always stick to marked cycling paths.

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

The touring cycling routes around Windsor cater to various difficulty levels. You'll find a good selection of easy routes, often characterized by flat terrain and well-maintained paths, suitable for casual riders. There are also moderate routes that might include longer distances or slightly more varied terrain, offering a bit more challenge for experienced touring cyclists.

Most popular routes around Windsor

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