Running in Medway 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 Medway—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 6, 2025

241

runners

1. Running loop from Brompton

8.05km

00:50

50m

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

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Intermediate

135

runners

2. North Mast Pond loop from St. Marys Island

6.91km

00:43

20m

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

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Intermediate

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114

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3. View of the River Medway loop from Rochester

16.5km

01:45

130m

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

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100

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4. Sharp's Green Pond loop from Brompton

12.7km

01:19

70m

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

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4.0

(1)

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5. Holly Hill Viewpoint – Dode Church loop from Cuxton

24.0km

02:51

400m

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

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6. Meadows Woods – Rochester Castle loop from Troy Town

11.4km

01:13

110m

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

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7. North Mast Pond loop from Twydall

14.1km

01:29

80m

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

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8. Sharp's Green Pond loop from Gillingham

8.25km

00:51

30m

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

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9. Rochester Castle loop from Cuxton

11.7km

01:13

110m

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

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5.0

(1)

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10. Capstone Farm Country Park loop from Hempstead

8.85km

01:06

150m

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

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Places to see

Castles

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

Isle Of Grain Halling Cuxton Cooling Stoke Allhallows Frindsbury Extra Great Chattenden Wood St Mary Hoo High Halstow National Nature Reserve High Halstow Cliffe And Cliffe Woods Hoo St. Werburgh

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Browse the best Running Trails & Routes in other regions.

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The best running trails in Medway

1. Running loop from Brompton

2. North Mast Pond loop from St. Marys Island

3. View of the River Medway loop from Rochester

4. Sharp's Green Pond loop from Brompton

5. Holly Hill Viewpoint – Dode Church loop from Cuxton

6. Meadows Woods – Rochester Castle loop from Troy Town

7. North Mast Pond loop from Twydall

8. Sharp's Green Pond loop from Gillingham

9. Rochester Castle loop from Cuxton

10. Capstone Farm Country Park loop from Hempstead

Other adventures in Medway

Most popular routes in Medway

Most popular attractions in Medway

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