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

Last updated: September 25, 2025

riders

1. Portland Bill & Chesil Beach loop from Weymouth

78.9km

03:42

930m

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

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Expert

3.5

(2)

riders

2. Tour of Britain stage, Burton Bradstock, Dorchester & Weymouth loop

92.1km

04:10

840m

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

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Intermediate

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4.3

(6)

1,080

riders

3. Rhododendron Mile – View of Weymouth Bay loop from Weymouth

96.6km

04:27

840m

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

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Intermediate

4.5

(4)

148

riders

4. Winters Lane – Cafe and Farm Shop loop from Weymouth

35.2km

01:49

320m

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

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Intermediate

124

riders

5. Chesil Beach – Weymouth Bay Beach Hut loop from Melcombe Regis

18.6km

00:46

110m

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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The best road cycling routes around Fleet

1. Portland Bill & Chesil Beach loop from Weymouth

2. Tour of Britain stage, Burton Bradstock, Dorchester & Weymouth loop

3. Rhododendron Mile – View of Weymouth Bay loop from Weymouth

4. Winters Lane – Cafe and Farm Shop loop from Weymouth

5. Chesil Beach – Weymouth Bay Beach Hut loop from Melcombe Regis

Other adventures around Fleet

Most popular routes around Fleet

Most popular attractions around Fleet

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