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 Orlando Southeast Trail and Coastal Anclote Trail . With more than 49 trails covering 524 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

Fort Fraser Trail

Nice Uncrowded 8 Miler

September, 2023 by bobm33567

I had a nice ride today at my first visit to the Fort Fraser Trail. Most of the trail parallels Hwy 98 so I wouldn't call this a deep in the woods nature trail but it is way off the highway so you feel safe. Trail was in excellent shape with only a few blind corners that encourage you to slow down. On this Friday afternoon there was very little pedestrian or bike traffic. Street crossings are well marked with stop signs and even the light poles have some cute motivational quotes printed on signs. Nice touch! I did find a diversion connector trail to the Circle B Bar Reserve. I will definitely go back there and explore some more.

Shingle Creek Regional Trail (FL)

peaceful

September, 2023 by ekhatchyb16

we had a blast riding in a group, enjoying the shade and sunny skies.

Withlacoochee State Trail

Hot and Boring

September, 2023 by mamadukes01

Started at Dunnellon and after several miles turned back. There is absolutely no shade whatsoever and not much to look at as it runs behind homes.

Accordion

South Lake and Lake Minneola Scenic Trail

S Lake/L Minneola

August, 2023 by mcconnellsts_tl

Great paved trails with exceptional facilities at S Lake; very scenic and enjoyable trail - we plan for the late morning to allow the "pros" to fly through the course double breasted (during the Tour de France), you understand. But mid-day was a great riding time.

Chain of Lakes Trail

for a local trail, it’s ok

August, 2023 by kuffs345

If you live in Polk Co and just want to ride without fear of getting hit by a car, then ok….although there are several areas where you have to cross streets and some of them being a little busy and questionable. We started at the south trailhead and once you get passed the homeless camps and run down industrial area, it’s a little better. I didn’t feel safe even though my husband was with me. I would never ride this trail alone. The bridges over the roadways are very steep and if you’re from Florida you might not be used to this kind of elevation. Glad it’s checked off our list but we won’t be back.

Auburndale TECO Trail

Ok for a short run or ride

August, 2023 by kuffs345

My husband and I were really looking forward to riding this trail. The parking area is nice and shaded which is nice to keep your vehicle cooler as opposed to sitting in the direct sun. There’s also restrooms here which is a plus…but if you’re looking to do more than 5 miles, this is not the trail for you. We hopped on our bikes and headed north. The tree canopy was great but just a couple miles up the path we’re huge power lines with NO trees or canopy and not scenic in the slighted.

General James A. Van Fleet State Trail

Highly recommend

August, 2023 by kuffs345

My husband and I went this weekend, we started in Polk City and rode our bikes north. Very scenic, the entire trail is shaded by a beautiful tree canopy. We saw several hawks, a blue tail skink and gopher tortoise. The air smells so fresh! It was a great ride. We’re definitely going back again soon!

Skyway Bridge Trail

Perfect ride.

August, 2023 by gatorsbabe2208

Great workout, amazing views!! Easy to get on the trail from Maximo park. Can sit and enjoy the bay at the endpoint rest-stop and refill your water. Trail could use some talc, but we’ll keep this on our list to enjoy again.

General James A. Van Fleet State Trail

Nice trail in the Forest.

August, 2023 by musakaevtimur

I'm riding a gravel bike and didn't notice anything bad on the pavement. I rode the part from Green Pond Road to the north, it was around 30 miles round trip. The day I was riding was very hot, over 90 degrees, but the good part is the trail is covered by trees, so it was great to have them)). All the way it smells good, like flowers, trees, swamps, sometimes cows. We enjoyed our trip so much.

Auburndale TECO Trail

great for an afternoon bike ride

July, 2023 by pmbrock63

We decided to start here and head up to the Van Fleet trail! Ended up making a 25 mile round trip bike ride !n. Will certainly be back

Starkey Wilderness Park Paved Trail

Not Skate-able

June, 2023 by eheiberger

Visiting from Ohio and looking for a trail to roller skate through the Florida wilderness. I thought this would be great but the asphalt looks like it hasn’t been maintained at all in the last 20 years. The portion along Starkey Blvd is maintained but not the 6 miles through the wilderness park. Very disappointing.

St. Cloud Lakefront Park Bike Path

I have done this trail first thing in the morning it does stay pretty busy. It is 2 miles each way. You have a choice of dirty or pavement. Nice trail on a relatively busy street with wild life and a resturants to the opposite side.

June, 2023 by lookinmoon

I have done this trail first thing in the morning it does stay pretty busy. It is 2 miles each way. You have a choice of dirty or pavement. Nice trail on a relatively busy street with wild life and a resturants to the opposite side.

Find Nearby City trails

Accordion

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.