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

Last updated: October 1, 2025

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1. Valley of Stones – Eggardon Hill Trig Point loop from Portesham

39.5km

02:07

620m

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

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Intermediate

5.0

(2)

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2. Valley of Stones – Litton Lakes loop from Portesham

29.6km

01:30

430m

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

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Intermediate

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3. Dorset Museum – Woodsford Castle loop from Martinstown

53.2km

02:41

480m

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

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4. Bockhampton Bridge – South Winterborne River loop from Martinstown

24.4km

01:16

200m

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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5. View of Weymouth Bay – View of Weymouth Bay loop from Martinstown

32.3km

01:57

490m

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

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The best road cycling routes around Winterbourne Steepleton

1. Valley of Stones – Eggardon Hill Trig Point loop from Portesham

2. Valley of Stones – Litton Lakes loop from Portesham

3. Dorset Museum – Woodsford Castle loop from Martinstown

4. Bockhampton Bridge – South Winterborne River loop from Martinstown

5. View of Weymouth Bay – View of Weymouth Bay loop from Martinstown

Other adventures around Winterbourne Steepleton

Most popular routes around Winterbourne Steepleton

Most popular attractions around Winterbourne Steepleton

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