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Windsor and Maidenhead

Windsor and Maidenhead

The best road cycling routes in Windsor and Maidenhead

4.6

(208)

7,772

riders

215

rides

In this guide, we’ve reviewed our full collection of road biking routes in Windsor and Maidenhead to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: November 5, 2025

4.5

(19)

riders

1. Pan flat Windsor loop via Drift Road

45.4km

01:46

140m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

4.0

(2)

riders

2. Ascot loop to the Surrey Cycleway

43.2km

01:46

270m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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4.5

(4)

417

riders

3. Windsor and Eton Bridge – Windsor Castle loop from Eton

32.6km

01:42

180m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

4.3

(4)

335

riders

4. Holyport Village Green – Bray Village loop from Windsor and Eton Central

66.7km

02:37

210m

220m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

4.3

(8)

312

riders

5. Devil's Hill Climb – Bottle Lane loop from Maidenhead

51.6km

02:13

300m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

4.8

(14)

275

riders

6. Holyport Village Green – Drift Road loop from Windsor and Eton Central

45.3km

01:53

130m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

5.0

(10)

213

riders

7. Windsor and Eton Bridge – Windsor Castle loop from Sunningdale

34.0km

01:27

200m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

5.0

(7)

189

riders

8. Golden Jubilee Statue – Golden Jubilee Statue loop from Sunningdale

28.7km

01:14

200m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

4.5

(2)

159

riders

9. Velolife Café – Bottle Lane loop from Windsor and Eton Central

47.5km

02:00

200m

210m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

4.6

(18)

188

riders

10. Bottle Lane – Hurst Village Pond loop from Maidenhead

44.1km

01:50

200m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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Didn’t find what you were looking for?

Check out more Road cycling routes throughout Windsor and Maidenhead below and find the perfect route in your destination.

Horton Waltham St Lawrence Sunninghill And Ascot Cox Green Bisham Shottesbrooke Hurley Eton White Waltham Sunningdale Datchet Wraysbury Old Windsor Cookham Bray

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The best road cycling routes in Windsor and Maidenhead

1. Pan flat Windsor loop via Drift Road

2. Ascot loop to the Surrey Cycleway

3. Windsor and Eton Bridge – Windsor Castle loop from Eton

4. Holyport Village Green – Bray Village loop from Windsor and Eton Central

5. Devil's Hill Climb – Bottle Lane loop from Maidenhead

6. Holyport Village Green – Drift Road loop from Windsor and Eton Central

7. Windsor and Eton Bridge – Windsor Castle loop from Sunningdale

8. Golden Jubilee Statue – Golden Jubilee Statue loop from Sunningdale

9. Velolife Café – Bottle Lane loop from Windsor and Eton Central

10. Bottle Lane – Hurst Village Pond loop from Maidenhead

Other adventures in Windsor and Maidenhead

Most popular routes in Windsor and Maidenhead

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