The best road cycling routes around Winslow
4.0
(14)
636
riders
41
rides
Last updated: October 7, 2025
3.0
(3)
124
riders
1. Crumbs Winslow Café – Whaddon Climb loop from Winslow
42.1km
01:46
300m
300m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
77
riders
2. Brill Windmill – View of the Brill Countryside loop from Winslow
97.3km
04:05
650m
650m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5.0
(2)
59
riders
3. Crumbs Winslow Café – Chilton Village loop from Winslow
76.7km
03:10
440m
440m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3.0
(1)
26
riders
4. Crumbs Winslow Café – Hogshaw Road loop from Winslow
33.9km
01:30
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
24
riders
5. Horwood Hill Climb – Evenley Village Green loop from Winslow
65.9km
03:00
410m
410m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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