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Windsor and Maidenhead

Windsor and Maidenhead

The best running trails in Windsor and Maidenhead

4.4

(101)

10,560

runners

432

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: December 8, 2025

4.4

(5)

155

runners

1. Windsor Estate circular via Thames Path

9.20km

00:57

30m

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

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Moderate

5.0

(2)

626

runners

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

11.3km

01:11

60m

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

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Moderate

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5.0

(1)

587

runners

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

21.3km

02:14

150m

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

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Hard

445

runners

4. Deer in Windsor Great Park loop from Windsor and Eton Central

8.87km

00:55

60m

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

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Moderate

3.0

(2)

223

runners

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

24.8km

02:40

40m

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

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Hard

1.0

(1)

210

runners

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

21.5km

02:19

30m

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

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Hard

4.7

(3)

185

runners

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

9.76km

01:00

30m

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

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Moderate

5.0

(3)

186

runners

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

15.5km

01:45

80m

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

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Hard

181

runners

9. The Long Walk – Deer in Windsor Great Park loop from Windsor

4.92km

00:31

20m

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

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Easy

5.0

(3)

170

runners

10. Deer in Windsor Great Park loop from Spital

10.00km

01:02

70m

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

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Moderate

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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

Castles

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

4. Deer in Windsor Great Park loop from Windsor and Eton Central

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

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

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

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

9. The Long Walk – Deer in Windsor Great Park loop from Windsor

10. Deer in Windsor Great Park 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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