Explore the best rated trails in Winston, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Orlando Southeast Trail . With more than 49 trails covering 527 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Very well maintained. Smooth ride. Approximately 6.5m from Lot 8 to East trailhead. Connects into the Suncoast Trail on the east end. About 80% sun so wear sunscreen and bring water. Saw dear. barred owl, woodpecker. Highly recommend
And the construction closure zones are quite large, IMO. Best stay off this trail in 2025 if you are biking and want to ride uninterrupted for more than 3 miles. 2 star rating as is, but I've done 15 miles o/b on this trail in the past rather enjoyed it.
We parked at Lake Townsen Park, had some lunch at Bree’s Provisions (They close at 2:00) and rode north, out and back for about an hour. The trail is well maintained and goes through beautiful farm country.
Started at Green Pond Trail Head and headed North. As reported, the trail has some pretty big bumps and a few holes, usually near the edge. With the limited traffic on the path, it isn't difficult to avoid them but you do have to keep your eyes on the trail. On 3/28 there was quite a bit of tree trimming and brush consolidation in the 10 miles between Green Pond and Bay Lake and some heavier equipment was staging at the State Park garage near Green Pond so maybe they are going to fix it this Spring.
The 10 miles between Green Pond and Bay lake is a very nice mostly shaded ride through timber with swamp land on both sides. There are 3 bridges about 2 1/2 Miles North of Green Pond which provides a place to watch alligators (this is mating season so you see some but there's a bunch more as the grunt and talk...), enjoy the birds and quiet serenity. At Bridge 2 that day, there is a 10+ Foot alligator nesting with her (soon to be) baby alligators.
North of Bay Lake is very nice and shaded for the 4 miles we traveled (Total round trip of 28 Miles).
Some call this trail 'straight and boring.' I'd suggest that it is quiet and serene, and, because it is straight and wide, you can spend most of your time enjoying nature!
I have seen so many close calls with small children and groups renting bikes and organizing standing on the trail when speeders come down the hill and fly past them. Killarney rentals should come out the side door and not directly onto the trail or slow the traffic down.
What a beautiful day on this part of the trail... well maintained, some many places to stop, site seeing, Sponge Docks, Monkey Farm, Shopping, Restaurants and libations.
The trail and the land needs to be cleaned up. The grass and weeds needs to mowed and garbage in the grass. The weeds are as high all along the trail by Trinity Blvd. You have a nice trail but the surrounding areas are filthy. It makes the homes /townhomes look shabby. How come Starkey doesn't have weekly maintaince on this empty lot???. She made promises when she was running telling us that this is going to be beautiful. Why not put some lights up for the darkness when walking or riding on this trail?????? The area around this trail is filthy and needs attention Asap!!!!!!
Great trail! But definitely needs some work after the Hurricane's North of Polk City. Trucks have created some dangerous dips/holes in the asphalt from the trail repair crews. BE CAREFUL. the Shade hides some of the obstacles.
You may encounter some equipment on the trail also during weekdays. Hopefully, it will get re-surfaced along this 2 - 3 mile stretch. I did NOT RIDE South of Polk City. Overall, a Very Nice trail. Will be back to 4 star trail after repairs.
It is a dream ride, all paved, scenic views from beginning to end. Stop off at Whiskey Joe’s for dinner or cocktails. Sandy beaches to sit on - easily make a day of this one trail and not wear yourself out.
Living in Apopka, I've been on portions of the West Orange Trail MANY times. Your description starts at the southern point at the bottom of Lake Apopka and ends with the words describing the trail ending at its southern point along Lester Rd. You should change the word "southern" to "northern". Otherwise, a nice description of a very nice trail. Thank you.
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