Find the top rated fishing trails in Winston, 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.
Teenagers and adult are now frequent with E bikes and motorize dirtbike
including golf Cart off wilsky's trail head. Racing off the grassfield and excessive speed on pave trails while other users are presents i am one of them. I am bringing this to your attention because i think it's getting out of control as a matter it is in my opinion. I have'nt notice any park official addressing this issue. I have seen your notice sign and this people seem to ignore it or dont see it. For the passed two months now they congregate @ 6PM till dark at the water stop. Thank You for attention.
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.
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.
Parked at Flatwoods Park where there’s restrooms and good amount of spaces. $2 to park. Paved road all the way around the loop and beyond. Several huts with giant water coolers. So nice on a hot day. Lots of folks riding, walking, skating. Everyone was respectful. Beautiful day. You get some shade from the trees but mostly open. On a hot day it’s best to go early.
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
Beautiful trail. We started at Peterson Park on the North end of the south half of this trail. It had all we look for in a good ride. Restroom at the trailhead, only one big intersection, wide paved trail through a covered quiet wooded area (mostly) and smiling congenial bikers and walkers. 14 miles there and back. After 365 miles this trip to Florida, it was the best trail!
Detour due to bridge closure. I was planning to connect to Bayshore and then the Courtney Campbell. ¿
This trail is so great !!! Smooth. Beautiful scenery and some tree art work along the way !! I’m so happy the Pinellas has a connection to this trail now in Tarpon Springs ¿¿¿
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.
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