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

Last updated: November 21, 2025

3.8

(5)

125

riders

1. Crumbs Winslow Café – Whaddon Climb loop from Winslow

39.8km

01:42

300m

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

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Easy

5.0

(2)

riders

2. Brill Windmill – View of the Brill Countryside loop from Winslow

97.3km

04:05

650m

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

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Moderate

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5.0

(2)

riders

3. Crumbs Winslow Café – Chilton Village loop from Winslow

76.7km

03:10

440m

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

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Moderate

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4. All Saints Church – The Soulbury Rollercoaster loop from Winslow

40.6km

01:44

310m

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

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Moderate

3.0

(1)

riders

5. Crumbs Winslow Café – Hogshaw Road loop from Winslow

33.9km

01:30

190m

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 Winslow

1. Crumbs Winslow Café – Whaddon Climb loop from Winslow

2. Brill Windmill – View of the Brill Countryside loop from Winslow

3. Crumbs Winslow Café – Chilton Village loop from Winslow

4. All Saints Church – The Soulbury Rollercoaster loop from Winslow

5. Crumbs Winslow Café – Hogshaw Road loop from Winslow

Other adventures around Winslow

Most popular routes around Winslow

Most popular attractions around Winslow

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