Find the top rated horseback riding trails in Winter Garden, 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.
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!
We had a great day on this path, it’s a little confusing to get to but well worth the effort.
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.
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.
Started at the Sargent park. Paved trail on a Saturday 8:30 morning was perfect. Paved part was 2.5 miles then you cross over on the 301 which has a nice crossing. Rest of the trail is gravel and dirt. Had no problem since it was dry. Definitely don’t go if wet, it’ll be too soggy. Beautiful surroundings. Knocked off a star because we couldn’t complete the trail due to a down tree. In total we did 10.5 miles. Since we started early we had shall the way.
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.
This trail is great. Beautiful scenery, great downtown area, lots to do!
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