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.
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.
One of the best non-paved trails in Florida. Yes the trail is rough but no rougher than the C&O Towpath. Lot of wildlife to stop and admirer.
There is a limitation on eBikes. The must be Class 1. Class 2 and Class 3 are prohibited
The trail has an eBike limitation of Class 1 so if you go beware
We had a nice leisurely ride around the lake on the sidewalk. Only saw one other person walking, and everybody was courteous enough to stand outside.
This trail is one of the most beautiful trails I’ve ever ridden on. I would bring earplugs though, because it’s really loud since you’re riding along a very busy highway.
Great for an out and back ride that is mostly tree covered and few road crossings. Saw a tortoise and a gator and lots of cows. Seems to be a place to sit and rest every few miles. Others say the trail is not in great shape - but for me who does not ride more than 11-12mph, I did not see problems. Did not see any place to refill water bottles.
When complete, this will be a great trail. But it is in different sections that are not connected. I only did the southern 2 sections on the map. Nice rides on picturesque trails.
Winter Garden is my favorite town to bike through. Lots of restaurants and shops along the bike trail. I always stop and enjoy. The rest of the trail is in good shape. Many great bike stations to stop and rest and get water. The last several miles of the north end are on-road with a lot of traffic and stop lights.
We biked the entire trail to Brooksville to the Withlacoochee trail and back. It’s 10 miles each way. The trailhead in Brooksville is at Russell’s park (off of Russell St, just south of Main St.). There is parking at the trailhead but no facilities. There is nowhere to get water and no bathrooms on the trail. For the first mile, the trail had lots of small tree limbs but it’s been very windy for the past 2 days so hopefully that’s not the norm. The rest of the trail was clean and smoothly paved. There are some little hills. The elevation change was around 370ft. I would ride it again.
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