Rails to Trails, for Smooth Florida Biking and Hiking

Florida promises a paradise for cyclists and hikers with a myriad of greenways and trails. Sunshine State pathways include nearly 60 trails transformed from abandoned railroad beds into playgrounds for outdoor enthusiasts, thanks to the Rails-to-Trails Conservancy, a national non-profit organization that's been busy for 25 years networking the nation with these beautiful paths.

Paved surfaces and gentle grades make rail-trails wheelchair-friendly and inviting to skaters. Numerous routes are paralleled by unpaved equestrian trails, and many offer convenient access to historic sites and other recreation, including links to other greenways. These welcoming paths roll through diverse environments, from scenic natural and coastal areas to picturesque towns; a few even cut through the heart of bustling cities - wherever trains once thundered across the landscape.

Read on to discover some favorites you won’t want to miss.

Van Fleet State Trail

Less than an hour from Orlando's glitzy attractions and crowds, you can escape to a deliciously secluded world of staggering natural beauty. During a journey on the 29.2-mile-long General James A. Van Fleet State Trail, you’re likely to have the path mainly to yourself.

The northern trailhead is sited by the almost invisibly small village of Mabel, while the southern end is located outside the town of Polk City. Shorter jaunts can begin at two mid-section trailheads. With the exception of the Bay Lake Road access point, which offers only parking, the trailheads offer restrooms, water and covered picnic tables.

The former railway corridor, once used to transport citrus, is flat and straight the entire way. But it’s hardly a snooze, with the path cutting through dense forests and the formidable Green Swamp; traversing rustic plank bridges spanning wide creeks; and passing next to ranches dotted with cows and Brahma bulls.

On this most rural of Florida's paved trails, the bird watching and wildlife viewing are stellar, and you’ll find covered benches or viewing stations every mile. Sunrise and dusk are the best times to spot white-tailed deer, wild turkeys, raccoons, otters and even bobcats. The trail has even acquired a reputation for its prolific butterfly populations, which peak in autumn.

After your jaunt down the trail, reward yourself with a hearty meal at one of the eateries close to the trail along Route 33, like the Red Wing Restaurant in Groveland, offering surprisingly fine fare that includes an assortment of hand cut steaks, fresh fish and game meat like quail and venison.

Fred Marquis Pinellas Trail

A green jewel that sparkles in a busy urban setting, the popular Fred Marquis Pinellas Trail reaches for 34 miles between St. Petersburg in the south and Tarpon Springs in the north, linking cities that include Palm Harbor, Clearwater and Gulfport with an eye-pleasing recreational corridor. Colorful railway-inspired artwork decorates the entrance to the towns along the way.

You're likely to share the trail with dozens of people biking, walking, jogging and rollerblading, but painted markers separate cycling and pedestrian lanes, and rangers and volunteers patrol the track answering questions and offering travel pointers.

Numerous cross-streets in downtown areas mean dealing with more traffic than on most rail-trails, but there's an agreeable trade-off: An abundance of shops, restaurants and coffeehouses are always close. Eight overpasses have been constructed to get trail-goers safely across busy highways.

The area’s bike friendly in multiple ways, with a bounty of bike rental shops as well as buses equipped with bike racks. With few minutes of bike-loading instruction, you're good to go -- literally.

To help navigate the trail with confidence, pick up a free guidebook issued by The Pinellas County Planning Department, available at libraries and trailside shops.

Tallahassee-St. Marks Historic Railroad Trail

Florida's first official state trail offers a rich diversity of sights and destinations. In fact, traversing the entire 16 miles of the Tallahassee-St. Marks Historic Railroad Trail is akin to time-travel: Starting amidst the urban amenities of Tallahassee, Florida’s state capital, you gradually slide into the past as the trail rolls along ancient forests and through picturesque rural towns. The southern terminus is located in the sleepy waterfront fishing village of St. Marks, where a rustic air of yesteryear still prevails.

You can hike, bike or skate on the multi-use trail, or even ride your horse on the adjacent unpaved trail.

Near the main trailhead in Tallahassee, off-road bikers can access the 15.8-mile Munson Hills/Twilight Mountain Bike Trails in the Apalachicola National Forest, a spur loop that curves through a lush, rare longleaf pine forest.

At Wakulla Station Trailhead you’ll have an opportunity for another worthwhile five-mile side trip, to Wakulla Springs State Park, a wildlife sanctuary that’s home to one of the deepest freshwater springs in the world.

When the scenery changes from towering pinelands to cabbage palms, you'll know you're approaching the coast. Work up a good appetite before arriving in St. Marks; the Riverside Café, with its gumbo, stone crab claws and a view of the St. Marks River, is the perfect way to refuel.

Gainesville-Hawthorne State Trail

You can discover the generous ten-foot wide, 16-mile Gainesville-Hawthorne State Trail on foot, via bicycle or even on inline skates—or explore the grassy trail that parallels it atop a horse.

The path begins at gorgeous Boulware Springs Park and Historic Waterworks, the site of Gainesville's first settlement, set among the forest on rolling hills. This trailhead, one of four, features picnic facilities as well as parking and a place to unload horses.

The beginning portion of the trail is distinguished by a series of small hills - a rarity among rail- trails. Riders not only get a modest uphill workout, but the thrill of speeding down the other side.

Gracefully arched plank bridges span several creeks along the countryside route, and informative markers provide details on the area's rich history of plantations, citrus groves and cattle ranches. Several tiny rail-station towns still survive.

Keep the pace leisurely and stop to enjoy the scenic Red Wolfe Pond, Little Sink and Alachua Sink overlooks. The trail passes by the Paynes Prairie Preserve State Park, a 22,000-acre preserve supporting a variety of species, from sandhill and whooping cranes to alligators and bobcats. After exploring the park's 30 miles of hiking, biking and horse trails, climb the 50-foot observation tower and simply enjoy the view.

Gasparilla Island-Boca Grande Trail

Lushly landscaped and impeccably maintained, the Gasparilla Island-Boca Grande Trail stretches the length of Gasparilla Island, a slender, six-and-a-half-mile barrier island. Yet trailside amenities encompass every quintessential Florida pleasure; you can shop and eat in the charming village of Boca Grande, explore historic sites like the Port Boca Grande Lighthouse and Museum, or ditch your shoes to search for seashells on the pristine white-sand beaches.
 

Withlacoochee State Trail

A long, leafy corridor through some of Central Florida’s most peaceful terrain, the Withlacoochee State Trail stretches an impressive 47 miles through Citrus, Hernando and Pasco counties, making it the longest paved rail-trail in the state. Built along a former Atlantic Coast Line Railroad route, the trail carries subtle nods to its past, including original railroad whistle markers that still stand along the route.

The ride passes through small towns like Inverness and Floral City, where oak canopies draped in Spanish moss create stretches of welcome shade. Highlights include the Inverness Depo District, which hosts markets in its pavilion and entertainment under the tower stage; the unpaved trails in the Croom area of the Withlacoochee State Forest; the Withlacoochee River (South) Canoe Trail; and Fort Cooper State Park.

Wildlife sightings are common, particularly in the more rural segments, and trailheads are well spaced for shorter out-and-back rides. With its smooth surface and gentle grades, the trail is equally appealing for long-distance cyclists and casual riders looking for a quiet escape.

West Orange Trail

A tapestry of history, charm and easy access, the West Orange Trail runs roughly 22 miles along the former Orange Belt Railway, linking communities from Winter Garden to Apopka. One of the most popular rail-trails in the region, it delivers a mix of scenery, from wooded stretches to vibrant downtown districts.

Winter Garden serves as a centerpiece, with its beautifully restored historic district, splash pad and frequent festivals creating a natural gathering point for trail users. Along the way, cyclists and pedestrians pass lakes, wetlands and neighborhoods, with plenty of opportunities to pause for a meal or coffee.

The trail is well maintained and clearly marked, with multiple access points and amenities including restrooms, water stations and bike rentals. Expect company — especially on weekends — but also a welcoming, community-oriented atmosphere that makes the experience part ride, part social outing.

The Legacy Trail

Tracing the path of the former Sarasota–Venice railway line, this 18.5-mile paved multiuse recreational trail rolls from Sarasota in the north to the Historic Venice Train Depot in the south. There, the ride’s only over if you want it to be, since the Venetian Waterway Park trail extends the path another four miles along the Intracoastal Waterway.

The pathway passes through a mix of suburban landscapes and natural Florida scenery, with shaded sections, open stretches and frequent rest areas. Elevated boardwalks and bridges span wetlands and waterways, some with stops where you can pull over and take in the scenery.

Multiple trailheads provide easy access, and amenities such as parking, restrooms and water stations make planning simple. With its smooth surface and gradual grades, the trail is ideal for riders of all skill levels, whether tackling longer distances or enjoying a relaxed cruise between stops.

Cross Seminole Trail

Following the route of the old Sanford and Indian River Railroad, the Cross Seminole Trail covers about 23 miles through Seminole County, a well-designed corridor that blends suburban convenience with pockets of natural beauty.

The trail links several communities, including Oviedo, Winter Springs and Sanford, and passes by Big Tree Park, Greenwood Lakes Park, and Spring Hammock Preserve, where you can meander through cypress forests on the way to Lake Jesup.

Frequent trailheads, clear signage and consistent maintenance make navigation easy, while connections to other regional trails expand riding options. With a mix of quiet segments and more active areas, it’s a versatile route suited for roadies seeking fitness rides as well as casual peddlers who favor leisurely outings.

Cape Haze Pioneer Trail

A quiet ride with a distinctly rural, Old Florida feel, the Cape Haze Pioneer Trail follows the route of the former Charlotte Harbor and Northern Railway for around 8.5 miles between Port Charlotte and Placida in Charlotte County. The trail’s straight, flat alignment reflects its railroad origins, making for easy cruising.

Surrounded by scrubby pine flatwoods and coastal vegetation, the trail offers a sense of remoteness despite its relatively short length. Interpretive signage along the route shares glimpses into the area’s railroad and agricultural history. Keep your eyes peeled for wildlife: Gopher tortoises abound, there's a bald eagles' nest with yearly visitors, and river otters near the Coral Creek bridge, as well as scrub jays, cardinals, and the occasional bobcat.

With limited road crossings and a peaceful atmosphere, the trail is well suited for riders seeking a low-traffic, uninterrupted experience. Trailheads with parking and basic amenities make access convenient for both short rides and full out-and-back trips.

Cady Way Trail

A mere four miles northeast of Orlando this urban pathway runs 6.5 miles through Orange County along what was once part of the East Florida and Atlantic Railroad. Today, it serves as a popular recreational route connecting neighborhoods, parks and schools.

The paved trail is smooth, well-marked, and a generous twelve feet wide, with two trail spurs that connect Lake Baldwin and Lake Susannah.  Along the route, users pass through green spaces and residential areas, with access points that make it easy to hop on for shorter rides or daily exercise.

While it lacks the long-distance feel of some rail-trails, its accessibility and convenience are part of its appeal. It features connections to restaurants, the Fashion Square Mall, Downtown Baldwin Park, and links to multiple other pathways as well, so it functions as both a standalone ride and a useful link within the region’s growing trail network.