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Winchester

Winchester

The best cycling routes around Winchester

4.5

(2)

199

riders

rides

Looking for the best cycling routes around Winchester? On this page, we bring you the best bike rides around Winchester so you can just get out and go. All you’ve got to do is choose your route!

Last updated: October 25, 2025

4.5

(2)

riders

1. Meramec Greenway Trail loop — Manchester

25.6km

01:27

60m

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

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Easy

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2. Baldwin loop — Manchester

52.0km

03:06

370m

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

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Intermediate

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3. Rock Hollow Trail loop from Wildwood

17.6km

01:36

280m

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

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Intermediate

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4. Riverscene Trail loop from Twin Oaks

12.5km

01:08

110m

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

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Easy

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5. Riverscene Trail loop from Wildwood

23.2km

01:49

230m

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

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Intermediate

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The best cycling routes around Winchester

1. Meramec Greenway Trail loop — Manchester

2. Baldwin loop — Manchester

3. Rock Hollow Trail loop from Wildwood

4. Riverscene Trail loop from Twin Oaks

5. Riverscene Trail loop from Wildwood

Most popular routes around Winchester

Most popular attractions around Winchester

Get inspired with the komoot mobile app

Explore more

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