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Windsor and Maidenhead

Windsor and Maidenhead

The best walks and hikes in Windsor and Maidenhead

4.6

(759)

9,808

hikers

437

hikes

Want to go hiking in Windsor and Maidenhead to explore more of this corner of

South East England? In this guide, we’ve reviewed our full collection of hikes and walking routes in Windsor and Maidenhead to bring you the best hiking routes in the region. To see which of our walks in Windsor and Maidenhead is the right one for you, browse real tips and photos uploaded by other hikers—and see what they had to say about each walk.

Last updated: November 26, 2025

4.6

(33)

251

hikers

1. Cookham to Marlow loop via River Thames

14.5km

03:47

90m

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

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Moderate

4.5

(15)

114

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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4.5

(14)

hikers

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

10.3km

02:36

20m

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

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Moderate

4.2

(10)

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

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

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Moderate

4.8

(10)

hikers

6. The Dew Drop Inn pub & Ashley Hill loop

5.94km

01:39

110m

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

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Moderate

4.5

(4)

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

(3)

hikers

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

16.6km

04:24

160m

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

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Moderate

3.3

(4)

hikers

9. Bisham Woods loop from Bisham

8.91km

02:24

110m

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

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Moderate

4.8

(17)

137

hikers

10. View of Windsor Castle – Deer Park, Windsor Great Park loop from Blacknest

21.7km

05:40

160m

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Hard

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Most popular attractions in Windsor and Maidenhead

Places to see

Natural Monuments

Castles

Lakes

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Didn’t find what you were looking for?

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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Browse the best Hikes in other regions.

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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 – Deer Park, Windsor Great Park loop from Blacknest

Other adventures in Windsor and Maidenhead

Most popular routes in Windsor and Maidenhead

Most popular attractions in Windsor and Maidenhead

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