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Windsor and Maidenhead

Windsor and Maidenhead

The best cycling routes in Windsor and Maidenhead

4.6

(247)

3,212

riders

194

rides

Cycling in Windsor and Maidenhead is one of the most enjoyable ways to explore more of this part of South East England. So you can find your perfect Windsor and …

Last updated: October 11, 2025

4.6

(36)

299

riders

1. View of the Jubilee River – Jubilee River Weir loop from Furze Platt

30.0km

01:51

50m

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

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Easy

4.6

(31)

245

riders

2. Jubilee River Weir – View of the Jubilee River loop from Dedworth

34.0km

02:02

70m

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

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Intermediate

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4.8

(25)

193

riders

3. Firework Ait – Cycleway by Deadwater Ait loop from Windsor and Eton Central

24.7km

01:32

170m

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

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Intermediate

4.5

(11)

119

riders

4. Ascot Racecourse – Guards Polo Club Sprinklers loop from Ascot

31.1km

01:55

240m

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

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Intermediate

4.8

(5)

riders

5. Marlow Suspension Bridge – Hambleden Village loop from Maidenhead

48.7km

02:58

370m

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

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Intermediate

4.0

(4)

riders

6. Jubilee River Weir – Jubilee River loop from Lyngfield Park

39.5km

02:26

130m

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

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Intermediate

4.5

(8)

riders

7. Firework Ait – Cycleway by Deadwater Ait loop from Windsor and Eton Central

48.9km

02:49

160m

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

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Intermediate

5.0

(6)

riders

8. Windsor Castle – Jubilee River Weir loop from Sunningdale

56.8km

03:27

260m

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

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Intermediate

4.7

(13)

128

riders

9. Firework Ait – Windsor Castle loop from Windsor and Eton Central

38.1km

02:21

310m

300m

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

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Intermediate

riders

10. Marlow Suspension Bridge – Hambleden Village loop from Cookham

40.8km

02:35

480m

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

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Expert

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Lakes

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Didn’t find what you were looking for?

Check out more 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 cycling routes in Windsor and Maidenhead

1. View of the Jubilee River – Jubilee River Weir loop from Furze Platt

2. Jubilee River Weir – View of the Jubilee River loop from Dedworth

3. Firework Ait – Cycleway by Deadwater Ait loop from Windsor and Eton Central

4. Ascot Racecourse – Guards Polo Club Sprinklers loop from Ascot

5. Marlow Suspension Bridge – Hambleden Village loop from Maidenhead

6. Jubilee River Weir – Jubilee River loop from Lyngfield Park

7. Firework Ait – Cycleway by Deadwater Ait loop from Windsor and Eton Central

8. Windsor Castle – Jubilee River Weir loop from Sunningdale

9. Firework Ait – Windsor Castle loop from Windsor and Eton Central

10. Marlow Suspension Bridge – Hambleden Village loop from Cookham

Other adventures in Windsor and Maidenhead

Most popular routes in Windsor and Maidenhead

Most popular attractions in Windsor and Maidenhead

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