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Chilmark

Chilmark

The best road cycling routes around Chilmark

4.2

(20)

820

riders

rides

Want to go road cycling around Chilmark? We’ve reviewed all of the road rides around Chilmark to identify the best. Explore them all here, and find your perfect road cycling route around Chilmark.

Last updated: November 28, 2025

5.0

(1)

riders

1. Lower Woodford Tree-Lined Road – View of Wylye Valley loop from Tisbury

72.1km

03:29

700m

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

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Moderate

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2. Beckford Pub – Cranborne Chase Village loop from Tisbury

40.9km

01:51

330m

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

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Moderate

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3. Cranborne Chase Village – Fonthill Arch loop from Teffont Magna

23.7km

01:13

290m

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

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Easy

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4. Fovant Downs Climb – Cranborne Chase Village loop from Tisbury

24.5km

01:28

340m

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

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Moderate

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5. Zig Zag Hill Climb – Gold Hill, Shaftesbury loop from Fovant

50.9km

02:44

610m

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

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Moderate

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The best road cycling routes around Chilmark

1. Lower Woodford Tree-Lined Road – View of Wylye Valley loop from Tisbury

2. Beckford Pub – Cranborne Chase Village loop from Tisbury

3. Cranborne Chase Village – Fonthill Arch loop from Teffont Magna

4. Fovant Downs Climb – Cranborne Chase Village loop from Tisbury

5. Zig Zag Hill Climb – Gold Hill, Shaftesbury loop from Fovant

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