Explore the best rated trails in Winter Haven, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Orlando Southeast Trail . With more than 43 trails covering 415 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.
We've ridden this trail for more than 20 years. Wildlife is a little more sparse these days, although we did see a deer and a turkey last week. It's a 7 mile one way loop (add 2 miles from the Bruce B Downs parking lot or 0.6 miles from the Morris Bridge Rd. entrance). It's in a fast growing area (New Tampa) but it doesn't take long to get away from civilization. There are some off road trails as well. It can get busy with fast riders and skaters. Parts of the main trail are going to need re-paving soon, but ample water stops and pleasant scenery make this one a lot of fun.
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.
always a great trail. so well maintained and marked. hence why we were surprised to encounter the large pile of sand close to marker 6160. both our bikes fishtailed. 3 other bikers were stopped. 2 others went to the highway to avoid.
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.
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
