Winter Haven, FL Running Trails and Maps

795 Reviews

Looking for the best Running trails around Winter Haven?

Find the top rated running trails in Winter Haven, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
39 Results
Activities
Length
Surfaces
Type

Auburndale TECO Trail

6.6 mi
State: FL
Asphalt, Concrete

Cady Way Trail

7.5 mi
State: FL
Asphalt

Casselberry Greenway Trail

5 mi
State: FL
Asphalt

Chain of Lakes Trail

4.2 mi
State: FL
Asphalt

Courtney Campbell Trail

10.5 mi
State: FL
Asphalt, Concrete

Cross Seminole Trail

22.8 mi
State: FL
Asphalt

Flatwoods Park Trail

7 mi
State: FL
Asphalt

Fort Fraser Trail

7.75 mi
State: FL
Asphalt

Gaston Edwards Trail

0.7 mi
State: FL
Concrete

Gertrude's Walk

0.25 mi
State: FL
Concrete

Good Neighbor Trail

10.3 mi
State: FL
Asphalt

Hammock Road Trail

3.7 mi
State: FL
Asphalt

Hancock Trail

6.5 mi
State: FL
Asphalt

Hardy Trail

0.9 mi
State: FL
Asphalt

Kewannee Trail

1.7 mi
State: FL
Asphalt

Kissimmee Trail Loop

6 mi
State: FL
Asphalt

Lake Apopka Loop Trail

14.6 mi
State: FL
Asphalt, Crushed Stone

Lake Baldwin Trail

2.5 mi
State: FL
Asphalt

Lake Jackson Trail

10.5 mi
State: FL
Concrete
Accordion

Lake Underhill Path

2.5 mi
State: FL
Asphalt, Concrete

Lake Wales Trailway

2.3 mi
State: FL
Asphalt

Little Econ Greenway

7.4 mi
State: FL
Asphalt

Mailer Avalon Trail

0.8 mi
State: FL
Asphalt, Concrete

Neptune Road Recreational Pathway

8.1 mi
State: FL
Asphalt

Old Fort King Trail

6.7 mi
State: FL
Asphalt, Dirt, Grass

Orlando Southeast Trail

13 mi
State: FL
Asphalt, Concrete

Orlando Urban Trail

2.6 mi
State: FL
Asphalt, Concrete

Pine Hills Trail

2.5 mi
State: FL
Asphalt

Sebring Parkway Trail

4 mi
State: FL
Concrete

Seminole Wekiva Trail

14 mi
State: FL
Asphalt

Shingle Creek Regional Trail (FL)

9.3 mi
State: FL
Asphalt, Boardwalk, Concrete

Suncoast Trail

42 mi
State: FL
Asphalt

West Orange Trail

22 mi
State: FL
Asphalt, Concrete, Dirt, Woodchips

Wilson Lake Parkway Trail

3 mi
State: FL
Asphalt

Withlacoochee State Trail

46 mi
State: FL
Asphalt, Boardwalk, Concrete
Trail Image Trail Name States Length Surface Rating
The Auburndale TECO Trail connects Lake Myrtle in Auburndale with Polk City, where it meets up with the General James A. Van Fleet Trail. The Auburndale TECO Trail is flat and invites walkers,...
FL 6.6 mi Asphalt, Concrete
The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Coy Drive in Orlando, just past the Fashion...
FL 7.5 mi Asphalt
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping.  The first segment...
FL 5 mi Asphalt
The Chain of Lakes Trail stretches for more than 3 miles along a former railroad bed from downtown Winter Haven to north of Lake Alfred in central Florida. As its name implies, you'll pass numerous...
FL 4.2 mi Asphalt
The Courtney Campbell Trail provides pedestrian and bicycle access along the southern side of the Courtney Campbell Causeway, linking two communities, Tampa and Clearwater, and two counties,...
FL 10.5 mi Asphalt, Concrete
Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...
FL 22.8 mi Asphalt
The Flatwoods Park Trail is located within a park of the same name. Flatwoods Park is just one of five parks that make up the Wilderness Park system. These parks include Trout Creek, Dead River,...
FL 7 mi Asphalt
Note: Per a Florida Department of Transportation press release, "The Fort Fraser Trail will be closed at the Banana Creek Bridge from April through fall 2016 due to construction. The remainder of the...
FL 7.75 mi Asphalt
In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the trail is also known as the Lake Ivanhoe Trail.) The paved route...
FL 0.7 mi Concrete
The General James A. Van Fleet State Trail runs 29 miles through some of Florida's most scenic rural landscape. If you are looking to immerse yourself in wetlands and wildlife, it will not disappoint;...
FL 29 mi Asphalt
Gertrude’s Walk spans three city blocks in downtown Orlando, providing access to offices and the city’s sports arena not far from its southern end. The trail runs adjacent to an active CSX and Amtrak...
FL 0.25 mi Concrete
The Good Neighbor Trail runs for just over 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The...
FL 10.3 mi Asphalt
The Hammock Road Trail parallels its namesake from Highlands Hammock State Park to Lake Jackson, allowing Sebring residents easy access between two of the city's natural treasures. The state park...
FL 3.7 mi Asphalt
The Hancock Trail is 6.5 miles of smooth as ice, undulating multi-purpose trail in Lake County, Florida. It’s wide - a good 14 ft - and the hilly topography can either be a moderate challenge or a...
FL 6.5 mi Asphalt
The Hardy Trail is a mile long walk or ride in the heart of Dade City. The trail sits on a converted railbed, and travels south from Church Avenue. Residents love using the trail to run or jog or walk...
FL 0.9 mi Asphalt
Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...
FL 1.7 mi Asphalt
Combining asphalt off-street paths and sections of sidewalk (particularly the eastern arc of the loop), the Kissimmee Loop provides access from the city’s residential neighborhoods to many amenities,...
FL 6 mi Asphalt
The Lake Apopka Loop Trail is nearly 15-miles. There’s an abundance of nature as well as some background history regarding the lake. Spanning across former farmland along the north shore, Florida’s...
FL 14.6 mi Asphalt, Crushed Stone
The Lake Baldwin Trail is a 12-foot wide multi-use trail that circles Lake Baldwin in Orlando Florida. The asphalt trail is wide enough to accommodate different types of users, including older...
FL 2.5 mi Asphalt
The Lake Jackson Trail circles this popular swimming and boating spot in the heart of Sebring. Trail-goers will enjoy waterfront views along the lake's sandy shores and connections to other trails in...
FL 10.5 mi Concrete
Accordion
The Lake Underhill Path is a greenway linking four parks in Orlando near the Orlando Executive Airport in downtown Orlando. Work out stations dot the length of the trail, which is why you might hear...
FL 2.5 mi Asphalt, Concrete
The Lake Wales Trailway is a 2.3 mile, 12-foot wide asphalt path that circles most of Lake Wales. The trail serves both as a recreational and transportation asset, thanks to its proximity to a number...
FL 2.3 mi Asphalt
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. The trail offers riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a...
FL 7.4 mi Asphalt
Neighbors in Avalon Park will appreciate this short local trail - a place to walk, bike and meet that's right on their doorstep. The trail runs just short of a mile east from the trailhead on Mailer...
FL 0.8 mi Asphalt, Concrete
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
FL 8.1 mi Asphalt
The Old Fort King Trail is a 6.7-mile mixed-surface trail in west Central Florida. The trail consists of two parts: starting from John B. Sargeant Park, a 2.2 mile paved portion heads north, along the...
FL 6.7 mi Asphalt, Dirt, Grass
The Orlando Southeast Trail is a collection of multiuse pathways crisscrossing Lake Nona, a master-planned community southeast of the City of Orlando. Narcoosee Road, running north-south, serves as...
FL 13 mi Asphalt, Concrete
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
FL 2.6 mi Asphalt, Concrete
Opened in 2017, Orange County's Pine Hills Trail spans 1.75 miles from Alhambra Drive to Silver Star Road in a western subdivision of Orlando. In the middle of the north-south route, a spur heads...
FL 2.5 mi Asphalt
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
FL 0 mi Asphalt
The Sebring Parkway Trail follows this major thoroughfare though downtown Sebring. Trail-goers will pass by three popular recreational attractions—Sebring Lake, Dinner Lake and Lake Jackson—as they...
FL 4 mi Concrete
Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...
FL 14 mi Asphalt
After 30 years of planning, the first segment of the Shingle Creek Regional Trail opened in Kissimmee in November 2016. The paved trail spans just over 1 mile, beginning near Steffee Landing, south of...
FL 9.3 mi Asphalt, Boardwalk, Concrete
About 20 miles west of Orlando, the South Lake Trail (also known as Lake Minneola Scenic Trail) takes in some of central Florida's most spectacular prospects. Nowhere in this region will you find more...
FL 13 mi Asphalt
Opened in 2001, the Suncoast Trail is part of Florida's Statewide Greenways and Trails System. The trail parallels the Suncoast Parkway, beginning in northern Hillsborough County, and heads north...
FL 42 mi Asphalt
The Town-n-Country Greenway is part of Tampa's network of trails and non-motorized greenways. You can access the paved trail from a parking lot on Webb Road, just south of Woodbridge Boulevard and on...
FL 3 mi Asphalt
Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...
FL 22 mi Asphalt, Concrete, Dirt, Woodchips
The Wilson Parkway Trail parallels the road of the same name, stretching north from Cherry Rd to its endpoint on Libby Rd. #3. It’s mostly a green ride, there’s not much variation in scenery. The...
FL 3 mi Asphalt
The 46-mile Withlacoochee State Trail is a must-do pure Florida experience for any trail enthusiast. Situated between Orlando and Tampa, it hosts a steady stream of visitors and locals on its paved...
FL 46 mi Asphalt, Boardwalk, Concrete

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Recent Trail Reviews

Lake Apopka Loop Trail

lots of wildlife!

July, 2021 by kippmich

Great ride for seeing wildlife. I’ve seen bobcats, alligators, panthers, turtles, birds, snakes, and more. The magnolia Park trailhead is closed but you can access the trail at the McDonald Canal or Green Mountain trailheads. Must use mountain bike as trail is mostly gravel. There are a few lookouts you can climb to get a better view of the area. There’s also quite a few covered benches along the way.

South Lake and Lake Minneola Scenic Trail

nice ride

July, 2021 by kippmich

I ride this trail frequently. It’s a little congested by Victory Park (by the lake) with walkers and joggers, but keep going and it thins out dramatically. Nice, pretty, almost flat ride. A lot of the trail is through woods with limited houses along the way.

Courtney Campbell Trail

loved it

June, 2021 by jeffdeitrick60

Beautiful trail. I did this with my son October 2020. Pretty much a straight run from st pete to Tampa. It runs along the side of a highway but zero danger. It’s separated by a shoulder and landscaping. You pass a few beaches along the way. There are a few bridges. Constant breeze through the ride over Tampa bay. Highly recommended.

Accordion

Auburndale TECO Trail

nice quiet trail

June, 2021 by jeffdeitrick60

This is our sixth trail that we have tried. Very smooth. Well marked mile markers. Not a lot of scenery. We went on a beautiful Monday in June. In the six mile trip we passed about 15 people. The people seemed very friendly. Much more so than other trails we’ve tried. Do not make a special long trip for this path. It would be a great trail if you’re in the area or live locally. As far as nature we saw lots of birds and four snakes. Harmless black snakes. Bathrooms were not plentiful and very dirty. No trash anywhere on the trail.

General James A. Van Fleet State Trail

Great trail

June, 2021 by moshe.t.guilaran

This is a wonderful trail just to see how far you can go. It’s 20+ miles of straightaway. The people are friendly and courteous as well. Minor animal spotting like gopher turtles and random non-venomous snakes.

Courtney Campbell Trail

waterfront trail arrive early on weekends to park

June, 2021 by johnforr

We are 70ish and rode this trail on our ebikes. We RV and try to do a couple trails a week normally in the 25 to 30 mile range. We parked in Ben Carson Park. Paid parking about 50 cents an hour paid at a kiosk with credit card or change. We arrived at 0900 on Memorial Day and there was plenty of parking. We got back at noon and all the parking spots were taken and entrances were blocked. My advice would be to park at a park in Safety Harbor and bike that trail down to this trail. This will be one of our favorite trails and we will return. reason for us to take out a subscription

General James A. Van Fleet State Trail

Deen Still Trailhead has limited parking

June, 2021 by bacarlson

There is only parking for 3 cars at best and it's just grass but not really a parking lot. There is one good spot and 2 that are a little sketchy. Beautiful trail with lots of shade here.

West Orange Trail

West Orange Trail is a must see destination

June, 2021 by foursluggers_tl

The West Orange Trail is now my home trail since I've retired. It's a safe, easy, and non-demanding trail with tons of scenery, lots of trees, and many convenient stops. Downtown Winter Garden is awesome. A few busier than desired street crossings interfere with the ride, but nothing too involved. The worst part of the trail are the wanna-be pro riders that zoom past you without any 'On Your Left' warnings. Kinda rude, but nothing to keep you from enjoying your ride.

Withlacoochee State Trail

beautiful!

May, 2021 by wendy moore

I have been on several different parts of this trail and love them all!

Lake Apopka Loop Trail

So Many Gators!

May, 2021 by ericamgray

The Magnolia Park Trailhead off Binion Road is currently closed and is torn up due to construction so you will be redirected to Lust Road. It’s a shame because it cuts off some scenic mileage - hopefully they’ll be done soon but the trailhead was really torn up. Without the Magnolia Park entrance it is all packed limestone which can get a little bumpy. Once you get going there isn’t any water until you reach Green Mountain Overlook. It was a beautiful ride with very little elevation change before Green Mountain Overlook.

General James A. Van Fleet State Trail

long and straight

May, 2021 by selbertson3

Definitely a ride through the wilderness. Water stations but little else along the way. Bring your own food as the is nowhere to purchase.

Withlacoochee State Trail

Nice Trail

May, 2021 by selbertson3

Nice ride with towns along the way. Good amount of shade as well with trail heads and water access along the way. Extension currently underway which will significantly increase the length.

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