Find the top rated horseback riding trails in Leesburg, 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.
This trail would be amazing if Pasco County had budgeted to make parking areas at the major road crossings. This includes Ridge Rd., Shady Hills Rd. and Countyline Rd. If you want to park at the trail, you have to drive to SR 54 or to Hernando County. Or you can get ticketed by Pasco County Sheriff's Office for parking under the overpass at Shady Hills Rd. For such a nice trail, it is almost completely inaccessible to Pasco County residents.
Nice long trail with wildlife and lots of shady canopy cover which is great in the summer. Saw an otter, tortoise, armadillo and many owls. Great time!
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
This trail is worth your time! Great surface and beautiful views especially at the bridge. I'm blessed to live near it.
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.
I did this ride with some friends when we parked in downtown Winter Park and rode over to meet up with the West Orange Trail. After a few miles, on side roads, it took to the Lake Apopka Loop Trail. It was a lot of fun. We saw gators, birds, and lots of other wildlife. I highly recommend sunscreen and making sure that you have plenty of water on a hot sunny day.
We started at Felburn Park, very nice with plenty of parking. Only 1 road crossing. Not much for shade but a nice view of the channel alongside the trail. Some bumps near the park. We did the trail twice. We would do this trail again.
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
We actually rode this trail February of 2026. Enjoyed the ride but grew desperate to find privacy to pee being a female. Did find a place but didn't notice trail markers for next time. Definitely would ride trail again.
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.
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