Looking for the best trails around Winston?

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 516 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.

Recent Trail Reviews

Neptune Road Recreational Pathway

on its way to something good

April, 2024 by sharon_wb

The northern portion is gorgeous with Waterview to the west and a nice ride through beautiful parks. I went a little further and did the regional trail just north of this one and it was absolutely beautiful but very short. The section after the high school heading north is dangerous for unsteady cyclist. The local community is actively working to improve this 3 to 5 mile section of trail Once that is complete the trail will be quite nice. The majority of the trail is a double wide sidewalk, so it is not good for a zone four or five ride. It is perfect for a leisure zone 2 ride. The Northern section is excellent for a family bike ride. On my way back heading south. I avoided the double wide sidewalk and rode the generous bike lane until it ended.

Ream Wilson Clearwater Trail

Good for running

April, 2024 by joenad55

Jogged the length of the trail recently in two separate runs. The bay portion very scenic, other parts tree covered and provide some shade. It goes through a couple of parks where there are benches and water fountains.

Duke Energy Trail

Nice trail

April, 2024 by joenad55

Well marked trail. Do have to cross over Drew St and 60, which can be a bit hazardous. Out in the open, no shade. Connects to the Ream Wilson Trail at the ballpark.


Withlacoochee State Trail

BEAUTY of a Trail!

March, 2024 by nume0112

On Easter, we parked in the Hernando lot and drove south to Floral City, before returning! Scenery ranges from beautiful partially shaded trails, several lakes and waterways, turtles, and alligators. LOTS of potential restaurants for a break (seafood, pizza, ice cream, etc.). We sat on the deck at Stumpknockers (5 blocks off trail) for an horsdoeuvre and bevvy! This portion of the trail was 29 miles round trip. We’ll be back to do the Northern portion!

Lake Apopka Loop Trail

Lots of wildlife

March, 2024 by bannerman

Pick a cloudy day and maybe a mountain bike. Lots of gators and birds. We started from the green mountain trail head and I would start at one of the other trailheads instead. They spent so much on the trail head that there is no money to maintain the trail and the first two miles are extremely rough.

Chain of Lakes Trail

Cute trail

March, 2024 by hitchcock.anita1

This is a short city trail ride but well maintained. There are sections of it which are quite pretty. There are amenities along the way, and with a Dunkin Donuts, 7-11, and a Diner at the trail end.

Clearwater Memorial Causeway Trail

review from a tourist

March, 2024 by luv_mlb25

So I ran this trail back in August 2023. The pictures submitted here on this site are very inviting, however, not valid. Yes, there is a spiral around the area of the trail, however, it is NOT part of the trail. That being said, I ran the spiral down to what I thought was part of the trail, only to get lost and realize that I had to run back up the spiral to get to the actual trail which then crosses the bridge. The sights, however, are amazing and I can't wait to run this trail again when I return in the fall. Once you get across the bridge and closer to the beach, there is more traffic, so keep your eyes and ears open. Great trail. Lots of sunshine and wide paths and beautiful flowers.

Oldsmar Trail


March, 2024 by jsb3144

No signs, street crossings are not working! When they are working the cars don’t obey. One has to sometimes get off the bike to push the button to cross the street. Not for kids at all!

Ream Wilson Clearwater Trail

Nice trail

March, 2024 by jpjjt

I just rode this trail and it’s very nice. The one problem is the trail bridge is out so you have to run the sidewalk to cross the 4 line road. Once you cross the road and get back on the trail it’s nice and easy.

Druid Road Trail


March, 2024 by jpjjt

The trail is nice mostly flat and well marked. I felt very safe riding the entire trail. You will go through a little part of Hoodish area but it’s very short. I recommend the trail and you can catch another trail on the way.

Duke Energy Trail

Great Trail

March, 2024 by jpjjt

I rode this trail yesterday 03/03/24 and it was amazing. I can’t wait to ride it again.

Starkey Wilderness Park Paved Trail

Great Trail...Trail information is a bit inaccurate

March, 2024 by 4jxs28d2k4

The trail is over 6 miles long if you start at the Starkey Park Bike Trailhead. The map on here that starts at Long Leaf is inaccurate. If you started at Long leaf and followed the path it would take you about 5 miles just to get to the park.

The park is free with ample parking and mostly good signage. There is a bathroom and water station at both ends of the nicely paved trail. Be on the lookout for snakes and tortoises on the trail!

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