A Roman city and the former capital under King Alfred the Great, cycling around Winchester offers more than a few slices of history to go with your rides. This beautiful …

Last updated: October 10, 2025

4.4

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1. South Downs loop from Winchester

41.8km

02:44

460m

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

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2. Meon Valley Trail and Swanmore loop from Exton — South Downs National Park

21.8km

01:22

150m

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

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3. River Itchen and Warnford loop from Winchester — South Downs National Park

54.3km

03:31

610m

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

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4. Trig point tour from Bishop's Waltham

46.4km

03:07

510m

500m

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

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5. Meon Valley Trail and Hambledon loop from Forest of Bere — South Downs National Park

45.4km

03:09

550m

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

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4.6

(22)

369

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6. The Deck at the Old Mill – Meon Valley Trail loop from West Meon

32.2km

02:26

210m

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

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Intermediate

4.7

(18)

339

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7. River Meon Picnic Spot – Meon Valley Trail loop from Botley

43.1km

03:07

370m

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

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Intermediate

4.6

(5)

282

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8. Meon Valley Trail – Beacon Hill – The White Way loop from Winchester

73.9km

05:53

1,110m

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

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5.0

(2)

147

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9. Westgate – Old Sarum loop from Winchester

81.6km

06:04

960m

Expert bike ride. Very good fitness required. You may need to push your bike for some segments of this route.

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5.0

(7)

124

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10. The Deck at the Old Mill – River Meon Picnic Spot loop from Wickham

18.7km

01:22

110m

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

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The best cycling routes around Winchester

1. South Downs loop from Winchester

2. Meon Valley Trail and Swanmore loop from Exton — South Downs National Park

3. River Itchen and Warnford loop from Winchester — South Downs National Park

4. Trig point tour from Bishop's Waltham

5. Meon Valley Trail and Hambledon loop from Forest of Bere — South Downs National Park

6. The Deck at the Old Mill – Meon Valley Trail loop from West Meon

7. River Meon Picnic Spot – Meon Valley Trail loop from Botley

8. Meon Valley Trail – Beacon Hill – The White Way loop from Winchester

9. Westgate – Old Sarum loop from Winchester

10. The Deck at the Old Mill – River Meon Picnic Spot loop from Wickham

Other adventures around Winchester

Most popular routes around Winchester

Most popular attractions around Winchester

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