The best road cycling routes around Windsor
4.8
(21)
1,024
riders
12
rides
Last updated: September 25, 2025
172
riders
1. Roadbike loop from Windsor
108km
05:19
1,340m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
Expert
4
riders
2. Westside Road – Hopmonk Beergarden 🍺 loop from Windsor
60.3km
02:36
320m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
Sign up for free
6
riders
3. Monte Rio – Moscow Rd back route loop from Windsor
180km
09:41
2,890m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
Expert
5
riders
4. Westside Road loop from Windsor
33.6km
01:29
220m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
6
riders
5. Moscow Rd back route – Gleason Beach loop from Windsor
136km
07:11
1,930m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
Expert
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular routes around Windsor
Most popular attractions around Windsor
Get inspired with the komoot mobile app
Explore more
Browse the best Road cycling routes in other regions.
Get ready to conquer new peaks
Sign up for Free