Explore the best rated trails in Windermere, FL, whether you're looking for an easy walking trail or a bike trail like the Leesburg-Wildwood Trail and Gardenia Trail . With more than 52 trails covering 441 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
This trail is great. Beautiful scenery, great downtown area, lots to do!
My husband and I rode this trail today (3-31-26) and had a great experience. The trail is well-maintained and the downtown area is so cute. We stopped a couple of times for lunch and coffee. I would highly recommend this trail. Beautiful trees and open spaces, with lots of rest stops throughout the ride.
I rode the southernmost 15 miles which starts in Owensboro, near Dade City. There’s a dirt parking lot there, but no restroom. The trail is smooth asphalt about six feet wide. Beyond that there are trees on both sides. At some points you can see thru the trees and see some ranch like land until you get into the Withlachoochee State forest. About 5 miles into the ride there is a restroom stop. At about 11.4 miles the asphalt gets older and a bit rougher but still is good- no tree roots or potholes. There is limited shade. At mile 15 we got off the trail and had lunch at Brees Riverside cafe. shade
Great paved trail. Lots of stop signed but smooth sailing otherwise
Wonderful trail. Do t forget get to stop at Vergi’s Pit Stop in Oak Hill. Best part of the trip!
There don't seem to be many outdoor spaces left in crowded central Florida that offer a quiet, removed experience. This trail has it in abundance, however. Running straight as an arrow through grazing lands, forest, and wetlands, it's almost a Zen-like experience as you cruise silently along the miles. Most activity is near to the trail starting points, so after a few miles away from those, you're left to yourself. One of the best, for sure.
Today Valentines Day was a gorgeous day for 17 of us Happy Wanderers to ride twenty miles of this trail.
The wooden nature walkway is currently under construction for safety reasons (they completely removed it) and I’m not sure when/if it will be reinstalled but I hope so. It was a nice little, brief excursion through the woods. The rest of the path is paved and perfect for a walk, bike ride or skating. It’s nice to have in my backyard
At the east end of the trail cross Canal St. and make a right. Trail/sidewalk runs along Canal. Cross rt 44 into Venetian Gardens where there is a beautiful path along Harris Lake.
We rode from Croom to the south end of this amazing trail. Smooth asphalt, shaded by a canopy of trees it was a quiet place to enjoy a Sunday afternoon.
Very dirty seemed to be people hanging out, possibly living on the trail. A few tents. Sketchy surroundings would not ride alone.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
