The best cycling routes around Windermere
4.9
(61)
422
riders
19
rides
Last updated: November 10, 2025
1. Belle Isle to Downtown Winter Garden — Winter Garden, Florida
32.3km
01:51
100m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
2. Dixie Lake loop — Lake Louisa State Park
91.2km
05:34
440m
440m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3. Eagle Nest Park loop via Lake Fran Trail —Orlando
12.9km
00:45
10m
10m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4.9
(14)
125
riders
4. Downtown Winter Garden – South Lake Trail loop from Winter Garden
48.9km
02:50
220m
220m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
17
riders
5. Downtown Winter Garden – Sugarloaf Mountain Road loop from Winter Garden
72.7km
04:22
560m
560m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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