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Windsor and Maidenhead

Windsor and Maidenhead

The best running trails in Windsor and Maidenhead

4.4

(93)

10,757

runners

441

runs

Running in Windsor and Maidenhead is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes in Windsor and Maidenhead—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: October 18, 2025

4.4

(5)

151

runners

1. Windsor Estate circular via Thames Path

9.20km

00:57

30m

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

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Intermediate

5.0

(2)

604

runners

2. Johnson's Pond – Virginia Water loop from Sunningdale

11.3km

01:11

60m

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

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Intermediate

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444

runners

3. Deer in Windsor Great Park – The Long Walk loop from Windsor and Eton Central

9.45km

00:59

80m

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

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Intermediate

222

runners

4. Windsor and Eton Bridge – The Long Walk loop from Windsor and Eton Central

33.3km

03:35

250m

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

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Expert

1.0

(1)

210

runners

5. View of the River at Dawn – Windsor and Eton Bridge loop from Windsor and Eton Riverside

21.5km

02:19

30m

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

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Expert

1.0

(1)

198

runners

6. Windsor and Eton Bridge – View of the River at Dawn loop from Maidenhead

24.8km

02:40

40m

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

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Expert

5.0

(3)

197

runners

7. Bourne End Railway Bridge – Cattle on Public Footpath loop from Cookham

15.5km

01:45

80m

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

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Expert

4.7

(3)

166

runners

8. Windsor and Eton Bridge loop from Windsor and Eton Central

9.76km

01:00

30m

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

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Intermediate

5.0

(3)

164

runners

9. Deer in Windsor Great Park loop from Spital

10.00km

01:02

70m

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

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Intermediate

131

runners

10. Deer in Windsor Great Park loop from Windsor

4.53km

00:28

10m

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

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Easy

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Other adventures in Windsor and Maidenhead

Greenwich to Fishguard — National Cycle Network Route 4

Cycling Collection by

Alice Baddeley

Walking in the footsteps of King John — Three Castles Path

Hiking Collection by

Kit P

Southern England in the footsteps of a king — hiking the Orange Way

Hiking Collection by

Kit P

Where red deer roam & history comes alive – Thames Valley Cycle Route

Cycling Collection by

Amy

Hike the length of Britain’s most iconic river — Thames Path

Hiking Collection by

Kit P

Ride six counties and the M25 – London Revolution loop

Road Cycling Collection by

David Bavin-Hobbs

Most popular routes in Windsor and Maidenhead

Hiking in Windsor and Maidenhead

Road Cycling Routes in Windsor and Maidenhead

Easy hikes in Windsor and Maidenhead

Waterfall hikes in Windsor and Maidenhead

Cycling in Windsor and Maidenhead

MTB Trails in Windsor and Maidenhead

Gravel biking in Windsor and Maidenhead

Most popular attractions in Windsor and Maidenhead

Places to see

Natural Monuments

Lakes

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Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Windsor and Maidenhead below and find the perfect route in your destination.

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

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The best running trails in Windsor and Maidenhead

1. Windsor Estate circular via Thames Path

2. Johnson's Pond – Virginia Water loop from Sunningdale

3. Deer in Windsor Great Park – The Long Walk loop from Windsor and Eton Central

4. Windsor and Eton Bridge – The Long Walk loop from Windsor and Eton Central

5. View of the River at Dawn – Windsor and Eton Bridge loop from Windsor and Eton Riverside

6. Windsor and Eton Bridge – View of the River at Dawn loop from Maidenhead

7. Bourne End Railway Bridge – Cattle on Public Footpath loop from Cookham

8. Windsor and Eton Bridge loop from Windsor and Eton Central

9. Deer in Windsor Great Park loop from Spital

10. Deer in Windsor Great Park loop from Windsor

Other adventures in Windsor and Maidenhead

Most popular routes in Windsor and Maidenhead

Most popular attractions in Windsor and Maidenhead

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