The best road cycling routes around Windsor
85
riders
14
rides
Last updated: September 21, 2025
4
riders
1. Plainfield loop from Cornish
32.8km
01:24
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
12
riders
2. Cornish-Windsor Covered Bridge loop from Windsor
47.0km
02:04
450m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
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14
riders
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
Expert
9
riders
4. Mt. Ascutney Climb loop from Windsor
27.0km
01:48
840m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
4
riders
5. Roadbike loop from Cornish
30.1km
01:22
340m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
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