Easy Riding

The Ultimate Guide to All 18.2 Miles of the Legacy Trail

What was built more than a century ago as a railroad to carry freight trains and passenger lines (and later the Ringling Bros. and Barnum & Bailey Circus) is now an 18.2-mile paved public park that stretches from Sarasota to Venice.

By Hannah Wallace January 4, 2024 Published in the January/February 2024 issue of Sarasota Magazine

Step onto the Legacy Trail on any given morning at any given spot between Payne Park and the Venice Train Depot, and you’ll be treated to a cross-section of car-free Sarasota: dog walkers and exercisers, inline-skaters and Razor scooters, Amish families, retired snowbirds and backpacked kids hurrying to school. You’ll see cyclists in all makes and models, including avid road riders in bright racing gear and people on e-bikes, trikes, fixies, beach cruisers and low-riding recumbents trailed by tall orange safety flags. At the same time, you might go long stretches on the trail seeing no one at all—hearing only osprey cries and the wind whispering through live oaks and muhly grass.

What was built more than a century ago as a railroad to carry freight trains and passenger lines (and later the Ringling Bros. and Barnum & Bailey Circus) is now an 18.2-mile paved public park that stretches from Sarasota to Venice. It’s equal parts thoroughfare and quiet nature trail.

For the last 40 years, “rail trails,” which convert disused train track corridors into public paths, have proliferated throughout Florida and the rest of the country. Some, like the popular 36-mile Pinellas Trail between St. Petersburg and Tarpon Springs, cut through decidedly urban landscapes. But the Legacy Trail, which was first established in 2004, stands out, in part, for its quiet, residential setting and long stretches of natural beauty.

“Typically, railroads are an ugly place to be, because they have to have access to industrial areas,” says Louis Kosiba, the president of the nonprofit Friends of the Legacy Trail, which supports the trail with fundraising, volunteers, advocacy and outreach. “Our trail really doesn’t get to be industrial until you get into the Nokomis area. Most of the trail is nice greenery.”

Those miles of greenery are paired with exceptional accessibility and first-rate maintenance. The predominantly flat, entirely paved Legacy Trail accommodates all ages and abilities, and virtually any mobility aid or device, from one end to the other. Users can access the trail via 15 trailheads with free parking, and many other entry points (both official and unofficial) are sprinkled along its length. 
The trail’s upkeep, managed by the county and supplemented by the Friends’ support, helps account for its popularity. Nearly 650,000 people used the trail in 2022, according to the Friends, marking a 50 percent increase over the previous year—an increase due, in large part, to the newly opened eight-mile northern extension to downtown Sarasota. Usage in 2023 had already reached 568,000 as of October, and December is typically one of the trail’s busiest months.

Because of that high-volume usage, maintaining the trail has become a priority for the county, and Sarasota’s relatively affluent, philanthropy-minded population ensures those efforts are well funded. Further upgrades are already in the works. This year will see the construction of pedestrian bridges over the trail’s busiest crossings at Bee Ridge and Clark roads. And talks are currently underway for a variety of improvement projects and extensions—including a multi-use recreational trail connector on the south side of Payne Park. 

“It’s extremely well kept, compared to the trails in other parts of Florida,” says Eric Johnston, a Venice resident who rides and rates Florida rail trails. After Hurricane Ian passed in 2022, he says, “the volunteers came out of the woodwork. The trail was cleared in like two days. You can tell the county takes pride and the people that are involved take a lot of pride.” 

Frankly, we’re proud, too, and this guide is our way of helping you explore and enjoy the trail, whether you’ve ridden it 100 times or have never set foot on it. Here’s what you need to know.

Caffeinate at Five-O Donut Co.

Caffeinate at Five-O Donut Co.

Trail bites

The Best Places to Eat on the Legacy Trail

If you’re planning a bike-and-brunch excursion, or you just need a delicious pit stop, there are a number of tasty, convenient options along the trail.

Starting at the north end of the trail, Café in the Park offers classy-casual Continental-inspired sandwiches (think caprese and prosciutto on a baguette, or a grilled Nutella) right in the middle of green, grassy Payne Park. And many cyclists use the trail’s Ringling Boulevard crossing to hit downtown Sarasota’s Five-O Donut Co. location for a coffee and a Long John—whether that’s at the end of a ride, or just the turnaround point.

Follow the trail east until it bends south and you’ll soon hit the Amish and Mennonite Pinecraft community. Der Dutchman Restaurant and Bakery has even posted a sign along the trail pointing users toward its hearty Amish meals and baked goods.

If you’re willing to venture half a mile west of the trail crossing at Webber Street, you’ll reach the busy Beneva Road intersection, which boasts several notable local eateries on all sides, including Solarzano’s, Salty Jim’s and the Parrot Patio. 
Not everyone can handle beer and biking (and we certainly urge doing so responsibly), but Calusa Brewing has been attracting slews of cycling tipplers since it opened near Clark Road in 2016. Calusa moved its taproom in late 2023, but the new location is less than a half-mile north on McIntosh Road and is convenient to reach from the Ashton Park trailhead. And—bonus!—it’s also the site of PigFish, James Beard-nominated chef Steve Phelps’ new sustainable seafood sandwich shop.

South of Sarasota proper, your next sit-down meal option is in Venice at Pincher's, the Florida-based seafood chain located at the trail’s Patriots Park trail access. A quarter mile farther south, just before you begin your climb over the U.S. 41 Bypass, you can refuel with some classic Chicago eats and sports bar grub at Joey D’s.

If you hit the Train Depot and your stomach is still empty, the Legacy Trail’s southern terminus sits just over the Venice Avenue Bridge from the historic downtown shopping district with grills, trattorias and hangouts like Daquiri Deck and Venice Avenue Creamery. Not that your options have to end there. Many ambitious bikers hungry for a beachfront nosh carry on past the Venice Municipal Airport to Sharky’s on the Pier, about three miles away.

The Venice Depot is the trail's southern terminus.

The Venice Depot is the trail's southern terminus.

Hop On

Where to Find a Trailhead

The Legacy Trail’s notable accessibility extends to the number and quality of trailheads and public access points it has. Over just 18.2 miles, the Sarasota County parks department manages 15 trailheads that include dedicated free parking. Eleven of those are public parks in their own right, with restrooms and other amenities. (The longest stretch of the Legacy Trail without restrooms is less than four miles, in the Palmer Ranch area between Culverhouse Nature Park and Osprey Junction.)

In addition to typical park amenities like playgrounds, water fountains and picnic tables, most trailheads also have a bicycle repair station equipped with a bike stand and specialty tools, plus a bike pump with two different valve fittings. 
And some of these access points are attractions in and of themselves. The Pompano Trailhead, between the Tuttle Avenue and Beneva Road crossings, and the Nokomis Community Park both offer pickleball and volleyball courts and indoor facilities that are available for rent. Payne Park even has a skate park and a nine-hole disc golf course with water features—not to mention its own café. 
If you’re within riding or walking distance, you can also access the trail from bike paths and sidewalks at any public road intersection, including the crossings at Bahia Vista Street in Pinecraft, Webber Street near Southgate, and Central Sarasota Parkway. (Visit scgov.net for a comprehensive rundown of county-run Legacy Park trailheads.) 

Kick Back and Relax

The Surrey With the Fringe on Top

Sometimes you just want to let someone else do all the work. Powered by a volunteer surrey-peddler, the county’s free Legacy Trail Surrey offers 45-minute guided tours for up to four passengers on Tuesdays and Wednesdays during certain times of the year. (Passengers in the back row have the option of pedaling, too, if they want.) Tours leave from the Sandra Simms Terry Community Center in Nokomis at 10 a.m., 11 a.m. and noon, and reservations are required. Click here to reserve.

Get Connected

The Legacy Trail Is Just One Among Many

For some folks, 18.2 miles is just the beginning of their journey. If you’re cycling the Legacy Trail, you’ve got options.

Starting from the trail’s official southern endpoint at the Venice Train Depot, the Venetian Waterway Park trail continues south for another four seamless miles, along either side of the Intracoastal Waterway, and takes you all the way to Shamrock Park and Caspersen Beach.

Or take the trail’s Nokomis Riverview Park access exit east to Florence Street/Edmonson Road/Border Road, which provides a combination of bike lanes, low-traffic roads and multi-use trails over I-75 to Deer Prairie Creek and eventually to the newly opened, fully paved North Port Connector. All told, getting to the connector adds 14 miles to your journey.

Supporters also hope to eventually connect the Legacy Trail north to the Florida Gulf Coast Trail, a proposed 336-mile, seven-county corridor, via downtown Sarasota and Longboat Key.

Other planned and proposed connectors include links to the recently reopened Bobby Jones Golf Club, the Celery Fields and Nathan Benderson Park. 

The bridge over Roberts Bay offers spectacular views

The bridge over Roberts Bay offers spectacular views

Sights for Sore Eyes

Fun Destinations and Scenic Spots

As the cliché goes, it’s not about the destination on the Legacy Trail, it’s about the journey. And the trail provides plenty of interesting spots to brake for on your trip.

Folks stepping onto the trail’s southern endpoint for the very first time may feel a surprising twinge of childhood nostalgia, and here’s why: Look closely during the opening scenes in Disney’s animated classic Dumbo, and you may recognize the Venice Train Depot in the long row of peach-colored archways depicted alongside the departing circus train. It’s not official, but the movie’s 1941 Florida setting would have historically implied a Sarasota County location, and it’s impossible not to see the similarities.

Built in 1927, the depot is now a historic park in and of itself, with exhibits and free tours at select times. The site also displays a 1953 Pullman train car formerly owned by the Ringling Bros. and Barnum & Bailey Circus.

At other points, the trail has wide-open water views—specifically from the bridges over Dona Bay/Shackett Creek and Roberts Bay. Less than a mile apart, these two concrete spans sport metal railings and mid-bridge breakout points for stopping and admiring the peaceful waters and occasional passing manatees. The Dona Bay crossing, the more dramatic of the two, also makes for popular sunset viewings. Post those pictures proudly: With no parallel roads or bridges nearby, these particular vantage points are exclusive to Legacy Trail users alone.

Nature lovers have plenty to ogle along the trail, especially during the two miles that cut directly through Oscar Scherer State Park. Known for its population of endangered scrub jays—a bird species that can only be found in Florida—the 1,400-acre Oscar Scherer is more than a day’s adventure in and of itself. But it also makes for an idyllic picnic pit stop for trail users who ultimately want to keep moving.

Not that nature stops at the park borders. North of Oscar Scherer, the trail skirts golf courses at Stoneybrook and TPC Prestancia, plus natural areas in Palmer Ranch and Culverhouse Nature Park. Gopher tortoises, box turtles, ospreys and bald eagles, deer, bobcats, many types of snakes, dinosaur-like sandhill cranes and even alligators are all common, but still thrilling, sightings. The trick is whipping out your phone fast enough to take a picture.

While you’re scanning the trail’s sidelines for critters, keep an eye out for the stout white obelisk mile markers, labeled with numbers in the 800s that get larger as you travel south. These historic railway remnants actually tell you how far you are from Richmond, Virginia—the northernmost point of the Atlantic Coast Line railroad.

The southern part of the trail may be rich in nature, but real estate looky-loos can savor neighborhood views in the north. Many homeowners have refurbed their landscaping to accommodate trail-side barbecues—or just to improve the view. (There are plenty of privacy fences, too. Not everyone welcomes the parade of strangers through their neighborhoods.)

Among those who have embraced the trail in their backyards, some have even added small bridges over the low-lying trailside edges to create their own private access points. Some of these spans are little more than a broad board over a ditch; some are bucolic little wooden arches amid the cattails; and in one case, a Sarasota homeowner has built a working drawbridge that provides access only when they allow. (These private access points are technically prohibited by county regulations, though authorities have yet to push the issue. But do not use these bridges without the owners’ permission. That’s called trespassing.)

If you find yourself inspired by nature on the trail—or all the backyard landscaping you’re taking in—you can always stop at Your Farm & Garden, which abuts the north trail’s Beneva Road crossing with an eye-popping selection of plants and outdoor supplies. You can finish up your ride with a couple of choice seed packets or a whole bike basket full of primrose and morning glory for your home garden. What better way to remember the trail?

The trail has multiple spots to stop for repairs

The trail has multiple spots to stop for repairs.

Ride in Style

Rentals, Repairs and Retail

No bike? No problem. A number of rental outlets near the trail offer bikes and e-bikes (and in some cases, trikes and recumbents) to rent by the hour or the day. Other shops provide rental service for pickup and even delivery, bringing bikes to you at designated spots on the trail.

And if you do have your own bike or e-bike (or you’re ready to buy), traditional bicycle repair shops near the trail are being joined by a growing number of specialized e-bike retail outlets and on-site mechanics.

“I would definitely call our shop a Baby Boomer shop,” says Pamela Fiume of Big Bam Bikes, which sells and rents e-bikes on East Venice Avenue, about 300 yards from the Venice Train Depot trailhead. “Our average age is probably 72, and most of them are snowbirds.” A four-hour e-bike rental can easily take you the full length of the trail, all the way to downtown Sarasota and back, with enough time to make stops along the way. The e-bikes offer varying levels of pedal assistance, as well as a throttle, to handle bridge climbs and ease fatigue. “People come back with a huge smile on their face,” says Fiume.

On the other end of the trail, at the crossing on downtown Sarasota’s Ringling Boulevard, cyclists with mechanical issues like flat tires are greeted by a welcoming black-and-white sign that reads “Bike Shop” in big block letters. There, Pinnacle Wheel Works has been serving road cyclists and mountain bikers of all skill levels for 10 years, and since the 2022 extension opened, the Legacy Trail brings bicycles right to the shop’s doorstep. The shop is all repairs and adjustments (not much retail) and stocks loads of replacement parts—all the better for quick turnarounds. “We try to get everyone’s bike back to them by the weekend so they can be out there,” says co-owner Chris Slack.

Just around the corner, the newly opened Crank and Paddle gives prospective e-bike buyers a chance to test-drive a wide variety of styles on the trail itself. Other rental, repair and retail options include Endless Summer, Florida E-Bikes, Legacy Trail E-Bikes, Legacy Trail Bike Rentals and Venice Bikes and Trikes. 

The Great Divide

E-Bikes and Traditional Bicycles

Tensions between motorized e-bike riders and traditional cyclists raise questions about who gets to use the trail—and how.

Take a leisurely stroll or meandering bike ride on the Legacy Trail, and within five or 10 minutes you will no doubt be easily passed by someone riding a bicycle or tricycle with an electric motor. Sometimes they’re not even pedaling, just zipping along, and if the passing driver is going especially fast or recklessly, the experience can be startling and even unsafe. Some trail users lament that these motor-powered vehicles, which might require minimal (or no) physical effort to surpass the trail’s 15-mile-per-hour speed limit, are even allowed at all.

“There’s like this big divide” between road cyclists and e-bike riders, says Venice’s Eric Johnston, who rides both a traditional cycle and an e-bike. Pamela Fiume of the Venice e-bike store Big Bam Bikes says many road cyclists consider e-bike enthusiasts to be “cheaters.” But e-bike advocates counter that motor-less 
cyclists can—and do—exceed the trail’s speed limit, too. And their speeds, especially when the cyclists pass unannounced, can also be galling for pedestrians and slower riders. In a 2022 Sarasota Herald-Tribune letter to the editor, the author dismissed speed-hungry road bike riders as “Tour de France-wannabe cyclists.”

According to Johnston, the issue isn’t the type of bike someone’s riding. “There’s a lack of education,” he says. “When I’m riding my bike, eight out of 10 times when another bike passes me, it’s a hotshot road [bike] guy.”

“People ask us to do something about e-bikes, but technically the county has approved the use of electronic bikes,” says Friends of the Legacy Trail president Louis Kosiba. E-bikes come in many different iterations. Any e-bike with a 750-watt motor or smaller, which can go a maximum of 28 miles per hour, is classified as a “bicycle” by Florida law. Enforcement of the trail’s speed limit comes down to the sheriff’s office, usually mounted patrols who “educate and ask for compliance,” according to a sheriff’s office representative.

But e-bike technology’s rapid proliferation and evolution, fueled at times by homemade upgrades, blur the line between bicycle and motorcycle. “There’s one class of e-bikes now that’s basically a scooter,” says Johnston. “And you occasionally get guys who have weed-whacker motors. I am totally for enforcing responsible riding.”

But, he argues, “the percentage of people who are abusing [e-bikes] is so small. The problem is etiquette.” And it’s difficult to legislate against impolite behavior, no matter what people are riding. Rather than relying on bans, proponents of coexistence emphasize the need for awareness and conscientious behavior. 
“I think the e-bikes are fine. It’s just the person using it,” says Pinnacle Wheel Works’ Chris Slack, an avid road cyclist. “I think announcing when you’re passing, slowing down when passing, being courteous—that’s helpful.”

Moreover, e-bike and electric pedal-assist technology have been a vital gateway onto the trail—and into cycling in general—for people with physical limitations. And that includes Sarasota’s significant population of seniors.

“I see a lot of people out [on e-bikes] who otherwise might not be riding a bike,” says Slack. “That’s hard to argue against. That’s a good thing.”

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