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 521 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.
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.
In three sections we completed this long trail, outstanding all through with side trips on connecting trails made for some longer rides. Many parts are tree shaded.
The scenery is really good. We completed the ride just before noon and the trail was still very shaded. The pavement is very smooth, making for a very pleasant bike ride.
This trail has been one of my favorites, lots of shade, a 13 mile r/t ride, no cars or related noise, but.. There are no bathrooms or water along the way, even where this trail ‘T’ intersects with the very noisy Suncoast Trail. My biggest gripe is the deteriorating condition of the trails surface, and each year it has gotten a bit worse. It’s still a beautiful ride though. The Good Neighbor Trail in Brooksville is now my favorite.
Used this trail from clearwater and hopped off to get to caladesi. Amazing best trail I’ve ever riden, lots of cute shops and restaurants along the trail for pit stops.
We stayed at a cabin in Lake Louisa State Park and drove to the winter Gardens trail head on plant Street. Although it was 30 minutes with traffic, we like the vibe of staying in the cabins when we’re biking. Plant Street is perfect because you can get your coffee at Foxtails before you leave, and get your beer at the Crooked can when you get back. We rode to the lake Minneola Trail in Claremont and back. Perfect day.
I didn’t see another way to provide this feedback. We parked a little further down Lutz Lake Fern and rode from there to the endpoint on VanDyke. Enjoyed the ride other than we lost a couple miles not parking where we originally wanted to.
Visiting the area and had my skates with me so woke up early and hit all the different paths down and back. All in all did just about 20 miles total and only hit each section twice (down & back). Now there are a couple boardwalk sections either made out of wood or those plastic planks so be careful hitting the one with plastic planks when there is morning dew on the ground. Some parts are definitely more scenic than others! Saw deer, alligators, squirrels, and ducks. Maybe next time I’ll get to see a swamp ape too! Also if you decide to start real early before the suns up I recommend getting some type of light with you as some sections can be pretty dark.
Great ride. Mostly shaded with lots of natural habitat to see. Would definitely recommend.
Started at John B Sargent Park and rode north up into the Hillsborough River State Park mostly through wooded trails. The first few miles are paved and follows along the east side of Hwy 301. Once you cross back over to the west side of 301, it's unpaved the rest of the way. I veered off the designated trail at Dead River road and headed west to the river and then north on a path that follows the river for a good ways. I eventually found my way into the park. The trails are very beautiful and secluded. It is a low lying area, so it's best to take this ride during a dry spell when it has not rained for a while. I did it on a hybrid bike with 32 cc tires without any problems. The entire trip was 25 miles and took me about 4 hours. Highly recommended!
Did the 46 miles and truly enjoyed it. Did it in three different sections. Will do this trail again soon.
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