Find the top rated fishing trails in Kissimmee, whether you're looking for an easy short fishing trail or a long fishing trail, you'll find what you're looking for. Click on a fishing trail below to find trail descriptions, trail maps, photos, and reviews.
I have ridden dozens of trails across Florida over the past several years and this one was by far the most confusing. I wanted to go from Lake Monroe trailhead all the way to Delon Park.. to get in close to 50 miles roundtrip.
It starts out great with mail markers along the way then off of a sudden you have to cross a major intersection, and pick up the trail where there is no signage the rest of the way.
I had to stop multiple times to check the online map to find the various turns and such that I had to make to stay on a trail. Then it just ends. The description does say there is a "gap"... but when you get to the end... you literally are at a dead end... nothing to tell you where or how to pick up the rest of the trail.
So I just went back to Lake Monroe and got a little over 30 miles.
Lake Monroe to Delon Park
I have done this trail several times now I once did it at midnight and I could honestly say I never felt threatened. The reason why I only do 3 star is because half of this trail you are literally next to traffic. Also if you don’t have the map on your phone you will definitely get lost they need to keep up with the maintenance of signs.
This is a nice trail for a quick ride, but nothing particularly special. It is well maintained with several parking areas along the trail. The easiest to access are the ones near USF at the northern trailhead and the other just south of Clubhouse Dr.
It didn’t have a ton of scenic, but there was a lot of shade so even if it was in the middle of the day, there was places where you could drive without being in full sun… I have ridden in about a year or so 14 mile ride was still doable my ride just
This trail is tucked away and is never very crowded. Numerous park benches around the trail and and the views are exceptional. Lots of wildlife.
Nice trail but not marked very well. If I was not following the map on trail link I wouldn't have any idea where I was. Part is just old sidewalks. You can start and stop at the Osceola welcome center on 192 but still no sighs for the loop trail
Great ttail. Follow it from Titusville to Lake Mary in March 3026. Other trails were also rode.
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.
Rode the WST for first time today. Started at the Owensboro trail head and rode 23 miles up to Floral City. So peaceful & quiet especially compared to Suncoast that we did earlier in the week. Was a very nice ride even though we did run into a couple of scary situations. Right where the good neighbor trail intersects with the WST there was a rattle snake on the pavement. Very thankful to the rider that came off the GNT and stopped and pointed it out to us. Without his heads up I likely would have ran over it. The 2nd scary event was coming back to the trailhead we had started at. Somewhere between mile 1 & 2 there were 2 large black dogs that came out of the woods and started going after my wife. Fortunately, I heard her screaming and looked back. 2 dogs chasing her and 1 of them was at her ankles. She got away by having to hit the throttle on the e-bike. Be aware.
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
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