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 South Lake (Lake Minneola Scenic Trail) . With more than 49 trails covering 526 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

Old Fort King Trail

Only 2 miles is paved.

September, 2024 by catnim2615

Only 2 miles is paved.

Withlacoochee State Trail

Trail is closed at the moment

September, 2024 by adamdb3600

Trail closed, drove to get here and found out with signs up at all the crossings in our area.

https://www.floridastateparks.org/parks-and-trails/withlacoochee-state-trail

Courtney Campbell Trail

Great views, mostly flat, minimal shade

September, 2024 by ebonysharie

A good trail for me as a beginner. There are benches scattered throughout to take breaks, but not much shade

Accordion

West Orange Trail

Courtesy

September, 2024 by lahlonvance

I’ve ridden this trail several times. The trail itself is awesome. Not too many busy crossings lots of shade. I really like riding this trail. The one thing that takes away from the experiences too many bike riders who are very rude riding for too fast for this trail, walkers, people, walking, dogs, pushing strollers, etc., also passing in spots where they shouldn’t be running stop signs it’s getting to be where it’s almost dangerous

Oldsmar Trail

A Messed Up Ride

August, 2024 by artofthesol

Beginning at the Oldsmar trailhead to Mobly Bayou Park.
It was a messed up ride: one minute you’re riding through lovely parks, then suburbia, then along the bay, then suburbia, & so on.
It went on & off like this throughout the whole ride. Signage was lacking for the most part, so be prepared to guess…a lot. Mobly Bayou Park is a lovely, but small park on the bay, with a wilderness preserve that has a one mile shelled path/trail.
Note: There is an extremely busy & dangerous intersection where three major roads intersect (Forest Lake Blvd./State Rd. 580/St. Petersburg Dr. W.) & this is where the crosswalk is located! We headed across cautiously with the "walk signal" & were nearly run down by careless drivers. Upon returning, we crossed at a much safer alternative.

Starkey Gap Trail

Lot's Of Wildlife

August, 2024 by artofthesol

Even though the trail is only 2.4 miles, we love this trail! It takes you through a rural area where we viewed numerous birds including Sandhill Cranes, Fox squirrels, Deer, Cows, Gopher Tortoises, and Coyote. There isn't much shade, but we were thankful for the clouds & light rain shower. We proceeded north to Starkey Park & crossed the very busy State Road 54. The crossing is west of Starkey Blvd. so we had to navigate this dangerous intersection twice.

Duke Energy Trail

Fun trail

August, 2024 by sandralynnsmith72

Short but fun trail!

Oldsmar Trail

This trail stinks!!!

August, 2024 by catnim2615

Follow this trail, I dare you to try. The trail stop, and starts, no signs! Try and follow it, I've tried 3 XS, I couldn't. I give up! This trail is on my never again list.

Lake Apopka Loop Trail

Reptiles & Birds

August, 2024 by jallen1804

Bumpy ride, & snakes, alligators, egrets, herons, & hawks. A nice afternoon ride.

West Orange Trail

The trail is great but...

August, 2024 by webmail1

It's getting so dangerous with all of the electric mopeds I'm afraid to ride or walk on it.

Flatwoods Park Trail

I ran this today. It is a great trail. It's impossible to get lost. There is mile markers every half mile. This is important because you loose the internet. The park ranger was very helpful, and friendly. I have to say this is a favorite now.¿

August, 2024 by catnim2615

I ran this today. It is a great trail. It's impossible to get lost. There is mile markers every half mile. This is important because you loose the internet. The park ranger was very helpful, and friendly. I have to say this is a favorite now.¿

Suncoast Trail

such an amazing trail with full of nice people

August, 2024 by abubeji5

I recommend every cyclist and runner … to check out this trail. It’s just amazing.

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Accordion

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