Find the top rated inline skating trails in Winter Garden, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
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!
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.
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