Explore the best rated trails in Winter Haven, FL. Whether you're looking for an easy walking trail or a bike trail like the Orlando Southeast Trail and Orlando Urban Trail. With more than 43 trails covering 386 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.
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.
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.
We had a great day on this trail. In good shape with considerable shade.
We parked near Winter Garden so we could have a beer and lunch.
We did an easy 30 miles out and back.
Wonderful riding experience through the "real Florida". Trail is in great condition and well marked, with frequent benches and rest areas. Scenic throughout with much wildlife viewing. Bluebird boxes have been placed along the length of the trail and are being well used by the birds. The area along the water near Inverness was a particular highlight, but the entire length of trail is worthwhile for repeated trips.
This may be the longest stretch of trail over water in the country, which made for a very unique ride. The entire trail parallels the highway, so expect noise the entire way. Even though the trail is well used, I had no issues riding at a good pace on a weekday, but I would expect weekends would be much more crowded. Easy to connect to the Wilson Clearwater Trail and Druid Road Trail to extend your ride as part of the Pinellas Trail loop.
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