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.
The route I went on was siren, and well kept up. It's now ine of my favs. I wish it was closer to me. ¿
We parked at Lake Townsen Park, had some lunch at Bree’s Provisions (They close at 2:00) and rode north, out and back for about an hour. The trail is well maintained and goes through beautiful farm country.
Been walking the trail for seven years and trail is becoming more and more popular for homeless camps in the woods. Witnessed a man beating a girl. Had a man pushing a shopping cart screaming at me telling me I am walking the wrong direction. More and more trash along the trail and food on benches . All good things come to an end.
Started at Green Pond Trail Head and headed North. As reported, the trail has some pretty big bumps and a few holes, usually near the edge. With the limited traffic on the path, it isn't difficult to avoid them but you do have to keep your eyes on the trail. On 3/28 there was quite a bit of tree trimming and brush consolidation in the 10 miles between Green Pond and Bay Lake and some heavier equipment was staging at the State Park garage near Green Pond so maybe they are going to fix it this Spring.
The 10 miles between Green Pond and Bay lake is a very nice mostly shaded ride through timber with swamp land on both sides. There are 3 bridges about 2 1/2 Miles North of Green Pond which provides a place to watch alligators (this is mating season so you see some but there's a bunch more as the grunt and talk...), enjoy the birds and quiet serenity. At Bridge 2 that day, there is a 10+ Foot alligator nesting with her (soon to be) baby alligators.
North of Bay Lake is very nice and shaded for the 4 miles we traveled (Total round trip of 28 Miles).
Some call this trail 'straight and boring.' I'd suggest that it is quiet and serene, and, because it is straight and wide, you can spend most of your time enjoying nature!
I have seen so many close calls with small children and groups renting bikes and organizing standing on the trail when speeders come down the hill and fly past them. Killarney rentals should come out the side door and not directly onto the trail or slow the traffic down.
Great trail! But definitely needs some work after the Hurricane's North of Polk City. Trucks have created some dangerous dips/holes in the asphalt from the trail repair crews. BE CAREFUL. the Shade hides some of the obstacles.
You may encounter some equipment on the trail also during weekdays. Hopefully, it will get re-surfaced along this 2 - 3 mile stretch. I did NOT RIDE South of Polk City. Overall, a Very Nice trail. Will be back to 4 star trail after repairs.
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