The best road cycling routes around Windsor
5.0
(1)
20
riders
9
rides
Last updated: October 19, 2025
2
riders
1. Lake Prince loop from Chuckatuck
75.6km
03:01
190m
190m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
2. Prudens Millpond loop from Chuckatuck
68.9km
02:51
190m
190m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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2
riders
3. Murphys Millpond loop from Chuckatuck
62.7km
02:38
160m
160m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
4. Lake Prince loop from Windsor
65.9km
02:35
180m
180m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
5. Prudens Millpond – Courthouse Millpond loop from Isle of Wight
34.2km
01:26
80m
80m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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