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Windsor and Maidenhead

Windsor and Maidenhead

The best walks and hikes in Windsor and Maidenhead

4.6

(778)

12,026

hikers

465

hikes

Walks and hikes around Windsor and Maidenhead offer a diverse landscape that combines natural beauty with rich history. This region in South East England presents a mix of forests, meadows, …

Last updated: October 12, 2025

4.6

(30)

242

hikers

1. Cookham to Marlow loop via River Thames

14.5km

03:47

90m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

4.6

(14)

111

hikers

2. Cock Marsh & The Bounty pub loop from Cookham

6.06km

01:33

30m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

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4.6

(12)

hikers

3. Ray Mill Island & Sounding Arch loop via River Thames

10.3km

02:36

20m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

4.1

(9)

hikers

4. Eton & Windsor loop via Eton College

6.03km

01:32

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

5.0

(6)

hikers

5. Hurley, Hambledon Weir & River Thames loop — Chiltern Hills

15.5km

04:00

70m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

4.8

(10)

hikers

6. The Dew Drop Inn pub & Ashley Hill loop

5.94km

01:39

110m

Intermediate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.

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Intermediate

5.0

(1)

hikers

7. Winter Hill, Bisham Woods & Cookham Dean loop

6.80km

01:51

100m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

5.0

(2)

hikers

8. Pinkeys Green, Bisham Woods, Cookham Dean & The Old Brick Works loop

16.6km

04:24

160m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

3.3

(4)

hikers

9. Bisham Woods loop from Bisham

8.91km

02:24

110m

Intermediate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

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Intermediate

4.9

(10)

447

hikers

10. View of Windsor Castle – Windsor Guildhall loop from Spital

13.3km

03:30

110m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

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Cycling in Windsor and Maidenhead

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Most popular attractions in Windsor and Maidenhead

Places to see

Natural Monuments

Lakes

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Check out more Hikes 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 walks and hikes in Windsor and Maidenhead

1. Cookham to Marlow loop via River Thames

2. Cock Marsh & The Bounty pub loop from Cookham

3. Ray Mill Island & Sounding Arch loop via River Thames

4. Eton & Windsor loop via Eton College

5. Hurley, Hambledon Weir & River Thames loop — Chiltern Hills

6. The Dew Drop Inn pub & Ashley Hill loop

7. Winter Hill, Bisham Woods & Cookham Dean loop

8. Pinkeys Green, Bisham Woods, Cookham Dean & The Old Brick Works loop

9. Bisham Woods loop from Bisham

10. View of Windsor Castle – Windsor Guildhall loop from Spital

Other adventures in Windsor and Maidenhead

Most popular routes in Windsor and Maidenhead

Most popular attractions in Windsor and Maidenhead

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