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

Last updated: October 20, 2025

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1. Start of the Rodwell Trail – Weymouth Jubilee Clock loop from Portesham

34.9km

02:12

310m

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

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Intermediate

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2. Ridgeway Hill – Max Gate loop from Winterbourne Steepleton

25.3km

02:00

240m

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

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Intermediate

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3. Hardy Monument loop from Martinstown

7.61km

00:32

150m

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

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4. View from Crow Hill – View from Eggardon Hill loop from Martinstown

57.7km

03:46

720m

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

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Expert

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5. Max Gate – The Great Field, Poundbury loop from Winterbourne Abbas

26.1km

01:32

130m

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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The best cycling routes around Winterbourne Steepleton

1. Start of the Rodwell Trail – Weymouth Jubilee Clock loop from Portesham

2. Ridgeway Hill – Max Gate loop from Winterbourne Steepleton

3. Hardy Monument loop from Martinstown

4. View from Crow Hill – View from Eggardon Hill loop from Martinstown

5. Max Gate – The Great Field, Poundbury loop from Winterbourne Abbas

Other adventures around Winterbourne Steepleton

Most popular routes around Winterbourne Steepleton

Most popular attractions around Winterbourne Steepleton

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