Running trails in Windermere, FL
Windermere has 1 trail in the directory. They're ranked here by rating weighted by review volume, across 17 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
Windermere Trails Greenspace Park
4.6 ★★★★★ 17 reviews
No trails match those filters.
How to pick a trail in Windermere
- Match the surface to your legs. Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one.
- Loop or out-and-back? A loop finishes back at the car with no backtracking; on an out-and-back you simply turn round at half your distance.
- Check the hours before a 6am run. Plenty of trails sit inside parks that gate at dusk and don't unlock until well after sunrise, so a trail that's perfect at lunchtime can be locked at 6am.
- The small things that decide it. 1 that runners describe as quiet. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Windermere trails by type
Running trails near Windermere
Worth the short drive — the closest towns with trails in the directory.