Find the top rated horseback riding trails in Winter Haven, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
I rode it down and back from Sorrento - part way into the Wekiva Trail. The trail is really nice in the middle - oaks, and parks, very pretty.
The southern end could be skipped as it has a lot of busy street crossing. A good place to start would be the Rooms To Go parking lot at mm 2.75.
There are2 tunnels under roads that are nice.
Street crossings could be marked better, need to pay attention when crossing - look for a No Vehicles sign and double yellow lines on the path at intersections (some are very faded). The path may jump sides or turn off, need to be attentive.
This is a beautiful ride with a very nice trail. Lots of cyclists, walkers, runners, and even roller blading. It’s very scenic and I felt safe by myself on this trail.
This 46 mile trail has a little of everything. Parts have nice shade, some areas are rural and some areas go through small towns. There are multiple access points. Highlights for us were Floral City near the midway point, Ft. Cooper State Park access, and Inverness where the trail skirts the water. There aren't many difficult road crossings and not many climbs to get over high intersection bridges. As of our last ride in 2025, the trail was in good shape. Not terribly crowded. An outstanding ride.
This is our first trail. It was quiet, peaceful & nicely paved. Friendly people walking & riding bikes.