Running around Middleton 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 around Middleton—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 19, 2025

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1. Beacon Hill – Pickering Castle loop from Pickering

10.3km

01:08

90m

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

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2. Pickering Castle loop from Pickering

9.48km

00:59

50m

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

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Intermediate

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3. Running loop from Pickering

6.31km

00:39

30m

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

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4. Featherhaugh Wood loop from Pickering

6.94km

00:44

50m

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

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5. Running loop from Cropton

9.13km

01:00

130m

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

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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The best running trails around Middleton

1. Beacon Hill – Pickering Castle loop from Pickering

2. Pickering Castle loop from Pickering

3. Running loop from Pickering

4. Featherhaugh Wood loop from Pickering

5. Running loop from Cropton

Most popular routes around Middleton

Most popular attractions around Middleton

Get inspired with the komoot mobile app

Explore more

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