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Winchester

Winchester

The best road cycling routes around Winchester

4.7

(365)

11,688

riders

523

rides

In this guide, we’ve reviewed our full collection of road biking routes around Winchester to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: October 17, 2025

4.7

(6)

183

riders

1. East Meon and Tichborne loop from Winchester – South Downs National Park

66.3km

03:06

690m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

4.5

(2)

riders

2. Winchester, Cheriton and Itchen Valley loop – South Downs National Park

51.6km

02:23

540m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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5.0

(3)

riders

3. Meon Valley loop from Winchester

61.6km

02:55

730m

Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Intermediate

4.8

(4)

riders

4. Arlesford & Avington Park loop from Winchester

54.0km

02:48

510m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

5.0

(4)

riders

5. A loop of the Churches & Cathedrals around Winchester

47.6km

02:10

540m

Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Intermediate

riders

6. Cheriton and Bishop's Waltham loop from Winchester – South Downs National Park

98.6km

04:32

970m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Expert

riders

7. North Waltham & Abbotstone loop from Micheldever Railway Station

76.4km

03:17

700m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

8. Hampshire century loop – South Downs National Park

161km

08:04

1,880m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Expert

4.5

(11)

244

riders

9. View of Avington Park and Lake – Avington Park Mansion and Lake loop from Winchester

26.3km

01:08

200m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

5.0

(5)

226

riders

10. Winchester City Gate – St Mary's Church, Itchen Stoke loop from Winchester

48.4km

02:05

410m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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The best road cycling routes around Winchester

1. East Meon and Tichborne loop from Winchester – South Downs National Park

2. Winchester, Cheriton and Itchen Valley loop – South Downs National Park

3. Meon Valley loop from Winchester

4. Arlesford & Avington Park loop from Winchester

5. A loop of the Churches & Cathedrals around Winchester

6. Cheriton and Bishop's Waltham loop from Winchester – South Downs National Park

7. North Waltham & Abbotstone loop from Micheldever Railway Station

8. Hampshire century loop – South Downs National Park

9. View of Avington Park and Lake – Avington Park Mansion and Lake loop from Winchester

10. Winchester City Gate – St Mary's Church, Itchen Stoke loop from Winchester

Other adventures around Winchester

Most popular routes around Winchester

Most popular attractions around Winchester

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