The best road cycling routes around Windermere
4.6
(27)
1,057
riders
42
rides
Last updated: November 3, 2025
4.8
(5)
181
riders
1. Downtown Winter Garden – West Orange Trail loop from Oakland
39.5km
01:40
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.7
(7)
99
riders
2. West Orange Trail – Downtown Winter Garden loop from Oakland
26.1km
01:01
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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15
riders
3. Lake Smith – Bluebird Pond loop from Independence
44.3km
01:51
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
8
riders
4. Bluebird Pond – Lake Smith loop from Lake Butler
69.5km
02:55
150m
150m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
5. Lake Smith – Bluebird Pond loop from Lake Butler
17.3km
00:50
30m
30m
Easy road ride. Great for any fitness level. 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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