Looking for the best trails around Winter Haven?

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.

Recent Trail Reviews

Withlacoochee State Trail

Classic Florida trail

March, 2023 by bklemz_tl

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.

Courtney Campbell Trail

Unique trail over water

March, 2023 by bklemz_tl

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.

General James A. Van Fleet State Trail

Nice trail, fast ride!

March, 2023 by bklemz_tl

Began at Green Pond trailhead, mm10. Was surprised to find the lot completely full by 10am on a Monday, but the holiday probably had much to do with this. Was advised they allow overflow parking along the shoulders of the parking lot and trail and I had no issues doing this.

Rode north 19.5 miles to the end at Mabel, then turned around back to Green Pond. Straight as an arrow & flat as a pancake the entire way. Only one real road crossing in that entire stretch. Very scenic throughout, although I thought the section between mm20 to mm25 north of Bay Lake trailhead was the highlight. Plenty of wildlife to keep you entertained.

I experienced none of the surface issues mentioned in other reviews. Some minor tree root bumps, many have been marked. Some filled potholes and a couple new sinkholes that were easy to avoid. I've ridden on much worse. Averaged over 14mph on the entire 39 mile ride & I typically consider anything over 12mph a fast ride.

Accordion

Lake Apopka Loop Trail

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.

March, 2023 by dnnyedy

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.

Flatwoods Park Trail

Flatwoods trails

March, 2023 by joerenn99

There is a limitation on eBikes. The must be Class 1. Class 2 and Class 3 are prohibited

Flatwoods Park Trail

Flatwoods

March, 2023 by joerenn99

The trail has an eBike limitation of Class 1 so if you go beware

Lake Jackson Trail

Nice ride

February, 2023 by shelly54

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.

Courtney Campbell Trail

beautiful ride, but really loud along highway

February, 2023 by drkateklemer

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.

General James A. Van Fleet State Trail

Great Out and Back Picturesque Trail

February, 2023 by jrmc21

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.

Shingle Creek Regional Trail (FL)

The South Sections are Nice Rides, but Trail is not Connected

February, 2023 by jrmc21

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.

West Orange Trail

Winter Garden The Best Cycling Town

February, 2023 by jrmc21

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.

Good Neighbor Trail

Nice trail

February, 2023 by kippmich

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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Accordion

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