Once Upon a Time in Florida

A Journey Through Old Florida With the State’s Last Cowboys

The seven-day, six-night reenactment offered 350 people on horseback the chance to push 500 head of cattle through 80 contiguous miles of Florida that few people ever get to see. 

By Isaac Eger August 31, 2023 Published in the September-October 2023 issue of Sarasota Magazine

A century ago, cattle roamed the beaches of Florida. There were no fence laws back then, and cows went where they pleased or wherever cowboys drove them. We forget that the first, true cowboys were from Florida, and that for years the Sunshine State was the top producer of beef in the United States. The first cows to set foot in this country arrived in Florida 500 years ago along with the Spanish colonizers, and while Florida isn’t even close to the same country it was half a millennium ago, its one constant has always been cows. 

The Spanish, the Seminoles and the Florida Crackers all made use of the cattle that grew accustomed to the sun and swamp of Florida. But you won’t see cows on the beach anymore, and it’s beginning to be less likely you’ll see cows on our ranches. Cow country, which once took up almost all of the state, has been whittled down to just a handful of pockets of wild Old Florida. 

To remind people of Florida’s vanishing cattle heritage, last December, for the fourth time in almost 30 years, the Florida Cow Culture Preservation Committee put on the Great Florida Cattle Drive—a seven-day, six-night reenactment during which 350 people on horseback pushed 500 head of cattle through 80 contiguous miles of Florida that few people ever get to see. 

A friend of mine had bought a $650 ticket to ride, but she injured her knee and couldn’t make it, so she offered me her place. It seemed like a commandment from the heavens. For months, I’d been dreaming of horses—horses in fields, horses on plains, even riding on the backs of horses through busy cities. Funny thing was, I’d never really ridden a horse before. I’d also never worn a cowboy hat or boots. As a kid, I never fantasized about being a cowboy; I wanted to be NBA legend Hakeem Olajuwon. But I’m in my 30s now and I feel like I’m making up for lost time by trying to learn as much as I can about Florida before it’s too late. Here was an opportunity to live out a different life, to travel through time and experience a part of Florida that’s almost all gone. How could I say no?

A river runs through precious, untouched acres of Old Florida.

A river runs through precious, untouched acres of Old Florida.

The drive started on an unusually hot Sunday afternoon on a private tract of almost 11,000 pristine acres southeast of Orlando. There would be no cows or riding that first day. The only ride we took was in our own vehicles to the Silver Spurs practice arena half an hour away in nearby Kenansville, where the drive would end the following Saturday. On the drive to the arena, you could see the creeping sprawl. Just-finished developments named after the very thing they destroyed lined the road, and developments in progress exposed the bone-white earth of Florida’s sandy soil like a compound fracture.

We took buses back to camp. I met my horse, Penny—a stout brown trail horse with a distended belly from all the baby horses she’d brought into the world—and received a crash course in riding from the woman who was leasing me Penny for the week. The instructions were simple enough: toes up, left goes left, right goes right, pull up to stop. Most people were too busy minding their chores to worry much about me. 

The one person who did pay me mind was Lynn Yarborough. She is the acting treasurer and vice president of the Cow Culture Preservation Committee, which has run the Great Florida Cattle Drive since its first event in 1995. “People think cows originated in Texas,” Yarborough told me. “But we want people to know that they came here first, and that Florida is a cattle state.” 

Yarborough is a fourth-generation Florida Cracker with a ranch north of Disney World. She takes pride in being a Cracker. “The rest of the world sees it as derogatory, but we Crackers embrace it because it’s our heritage,” she said. The etymology of the name is uncertain. It could come from the cracking of corn, or a Spanish bastardization of the word Quaker, but the story Crackers like to tell is that it comes from the crack of the whip cow hunters would use to rustle up loose cattle out of the brush. The Crackers would also use the whip to signal to one another from a distance. “My family would hear Uncle William cracking his whip on his way home, so they knew to get dinner ready,” Yarborough said. 

I asked her if I was a Florida Cracker. “If you were born here, you could say you were a Cracker,” she said. “But you’ve got to know how to hunt or fish or cut swamp cabbage—basically live off the land.” 

That night, the moon was big and I didn’t sleep much. I went outside my tent and watched the horses sleep on their feet and listened to them breathe.

A rider tacks up his horse under a full moon.

A rider tacks up his horse under a full moon.

The next morning, the camp woke before 5 a.m. while it was still dark. We packed our things, saddled the horses and ate breakfast. 

We were organized in circles, and each circle had its own boss and color. I was in the blue circle, the equivalent of being seated at the kids’ table. Because I was a novice, my riding companions were mostly children. Every day, a different circle got to work with the real cowboys up front, near the cattle. I wouldn’t see the cows at all that day. 

But I did get to meet some of the people who were on the drive. It wasn’t just Florida folk. There were riders from Pennsylvania, Texas, Montana and Brazil. We were all required to dress like cow folk from the late 19th century. That meant no T-shirts, baseball caps or Gore-Tex. I wore a straw hat I bought off Amazon, blue Wrangler jeans and a faux mother of pearl button-up long-sleeved shirt. Most everybody had a Southern twang, whether or not they were from the South. Even I noticed a thickening country lilt forming in my mouth when I spoke. 

Drive participants in period-appropriate clothing.

Drive participants in period-appropriate clothing.

Not everyone was a cowboy. One fellow on the drive, Bennett Lloyd, dressed like a poor Spanish soldier from the mid-16th century and walked on foot. Lloyd, the museum coordinator at the Museum of Seminole County History, wore a 16th-century-style long shirt made of linen under a billowing trunk hose and a front-button wool overcoat called a sajo. On his feet were leather slippers with no support. I asked him if it hurt to walk in them. “I’m used to walking long distances in kit,” he told me. “And actually, it’s better on the drive, because you’re not walking on pavement. Old shoes are not meant for painful pavement. They’re meant for dirt roads and gravel.” 

The Spaniards were the first to organize cattle drives in Florida. In 1521, Juan Ponce de León brought seven head of Andalusian cattle and a bunch of hogs with him to Florida. He was killed by a poison arrow from the native Calusa, but subsequent conquistadors brought more cattle and hogs to march alongside their hungry armies. Some of those cows and hogs escaped into the Florida wild and, hundreds of years later, the Scotch-Irish came to Florida and started hunting the escaped Spanish cows. 

The conquistadors left a trail of blood and horror behind them. I asked Bennett why he dressed up as one. 

“I want to experience something as close to what it was like 500 years ago as possible,” he said. “My job is to try to find tidbits from witnesses as close as we can get to any given event or scenario or lifestyle and to document them and to prove their importance. If I can be a witness to something for someone else in the future, then maybe that will help someone further down the line, whether it’s for just a thesis, or for preserving the land that is disappearing.” 

Remembering is always a complicated matter, and right now it feels more complicated than usual. Is it only painful to remember? If this kind of Florida is doomed and the new Florida is inevitable, wouldn’t it just be easier to forget? 

“I think the best way to approach history is to be honest, regardless of value judgments,” Bennett said. “You can objectively say that these people did what we can now call very horrible things. I don’t think you sugarcoat it. I don’t think you apologize for it. You just say it happened and this is our understanding now. We can be better than that. That’s part of why you teach history in the first place.” He then quoted the Pakistani-British historian Tariq Ali: “History rarely repeats itself, but its echoes never go away.”  

We don’t have any mountains to give us a sense of distance, but the land goes on forever.

Throughout the drive, we made lots of twists and turns. If I were to draw a map of the path we took, it would look like the crayon art of an angry child. While our clothes were faithful to the cowboy era, the path we took was not  historically accurate, because it’s not geographically possible to do a cattle drive of yore. Too much land has been developed. The old Cracker Trail traced 120 miles through Central Florida from Bradenton to Fort Pierce. Traveling it could take months. 

The land varied over the miles. Pine forests thick with palmetto turned into hot, open prairie that went on and on until we’d stumble upon pockets of oak hammocks that sat in the middle of the steamy land and offered a brief oasis of shade. 

The peak of Florida’s cattle days came after the Civil War, when trade with Cuba was at its height. “Years ago, we would have been driving cattle from Seminole County to the Caloosahatchee River and hitting barges,” Yarborough told me. “Then the rafts and barges would go to Cuba with the cows.” 

Cattle on the move

Cattle on the move

The cows we were working with were a mix: commercial cattle (bred to be slaughtered), Cracker cattle (a historic Florida breed), Corriente cattle (smaller and typically used for rodeos) and a handful of longhorns. We didn’t push the same 500 head of cattle throughout the drive, but instead switched out herds a few times as we changed ranches. Cows from different ranches can pick up dangerous pathogens if they march through unfamiliar land. Back in the day when there weren’t any fences, cows went where the grass was greenest. But in 1949, as Florida grew and cars were reaching deeper into the peninsula and coming into conflict with the wandering cows, then-Gov. Fuller Warren signed a law that required cattle ranchers to fence their livestock. 

Most of us only see the interior of Florida from the interstate, and it’s easy to feel bored by the landscape. But on a horse you see the real Florida. Yarborough told me some cowboy philosophy before the ride: You get in a car to see what man has made. You’ve got to get on a horse to see what God has made. 

I felt like I was seeing Florida for the first time—a Florida without a horizon. I forget just how big our state is. We don’t have any mountains to give us a sense of distance, but the land goes on forever. The sky looked like it was cracked open with heaven’s light. I felt stunned with wonder. 

We marched 18 miles that first day. When we arrived at camp after 6 p.m., the sun was barely up and everybody was beat. I was starving. After dinner, we were visited by Clint Richardson, the general manager of Deseret Ranch. He dressed like a cowboy, but his clothes had no wrinkles. Deseret takes up 312,000 acres of Old Florida and is owned by the Mormon church. It’s the second-largest plot of privately owned land in the state. 

Richardson told everyone about the importance of cattle and the church’s commitment to keeping Florida’s traditions alive. But he was also forthright about the church’s plans, which include developing much of Deseret. By 2080, more than 133,000 acres of the ranch and farmland are slated to be developed and filled with 500,000 residents, which would make the ranch Florida’s 10th largest metropolitan area. 

A cowboy moving cattle

Image: Isaac Eger

The next day, my circle was up front with the cows. By now, I felt good on the horse, which was basically on autopilot. I found that while my ass hurt at a trot, the whole ride was relatively pain-free. (In fact, it was more painful for me to sit down, hunched over my computer, to write this story than it ever was on horseback.) 

Since the drive happened during an unusually hot December, I was careful to hydrate. That meant I had to relieve myself a lot. One time, we were with the cattle in a big open plain and there were no trees or bushes for me to hide behind, but I couldn’t wait any longer. I went off to the side as far as I could and let it fly.

About halfway through, I heard cowboys shouting in my direction. A single cow had broken from the herd and was headed toward me. A moment later, the rest of the cows followed suit. I pulled up my pants while the stampede made a beeline at me. I tried to settle my horse and put my foot in a stirrup, but she kept moving away out of fear of the oncoming herd. I could hear the worry in far-off shouts. I jumped in the saddle, expecting to have to dodge the herd, but, thanks to some seasoned riders who saw the danger, the cows were steered away. Worry turned into amusement, and many riders took the opportunity to tease me for my near-mishap. “Best not to piss in the middle of a stampede,” one cowboy told me.

Cur dogs round up a loose cow.

Cur dogs round up a loose cow.

I was a gaffe machine. Either I was holding the reins wrong or putting on the tack backward or riding all goofy. For most of the drive, I was grabbing my brim and tipping my hat at anyone who said hello, until one rider told me I was only supposed to tip my hat to women. To men, you give a solemn nod. I was also mocked for my horse, which was far too short for my long legs. One cowboy asked if my feet would touch under the horse’s belly when I kicked. 

None of it bothered me, since I had no pride to begin with. I knew I wasn’t a real cowboy, and most of the folk on the trip weren’t real cowboys, either. You could tell who was real and who was playacting by how much, or how little, they talked. If you talk unnecessarily, you can spook the cows. 

I was lucky that the realest cowboy on the drive talked to me. I asked Billy Davis Jr. how long he’d been a cowboy. 

“All my life,” he told me. “And my daddy, and his daddy and his daddy.”

Even at 70 years old, Davis moved with ease. His skin is cut deep with sun. I bet he has never worn sunscreen. He smoked Backwoods Sweet Aromatic Cigars and had two or three cur dogs orbiting him at all times. He’s an eighth-generation Cracker and he has grandkids, the 10th generation. 

When I asked Davis if I was a Cracker, he was blunt: no. “You got to have generations behind,” he said. “You got to know how to read cattle, to push cattle, to be a cowboy or a Cracker. Most ain’t got no idea what it is to be a cowboy. Just because they walk out the store with a new hat or put some cowboy boots on don’t mean they’re a cowboy. And I don’t agree with it.” He paused and lightened his voice a touch. “But that’s just my opinion. I have to watch myself or I might hurt somebody’s feelings.” 

Davis was happy to be on the drive. He’d participated in every one since 1995 and said it’s important to acknowledge Florida’s heritage. “That’s the reason I became involved,” he said. “I think it’s very important to remember where we come from and the people that was here before us.” 

But he didn’t seem too hopeful about the future. “The kids nowadays can’t come help me,” he said. “I’ll send them to a pasture and tell them where to gather and they bring out their phone and track it. And if they get lost, they’ll call me. What in the hell did we do before we had phones? You cowboy up!” 

I asked him what it meant to cowboy up. 

“It means when you go, you ought to know where the hell you’re going and what you’re going to do,” he explained. “And that’s what’s the matter with these boys today. Their daddies and granddaddies had money, and it was gifted to them, and they knew that they didn’t have to excel in any damn thing because they got Mom and Daddy to fall back on. I didn’t and I wouldn’t. I’d die and go to hell first.” He softened his voice again. “But that’s just my opinion,” he repeated. “I’m set in my ways. And it is hard for me to change them at my age. I’m not going to dress up to be anything but myself.” 

Davis is also aware that if there isn’t any open land, there won’t be any more cowboys. “It’s mathematical,” he said. He doesn’t trust conservation easements that are set up by governments to protect Florida’s remaining wild land. “There’s just not enough land to carry on,” he said. “You look at what all is being sold and promised to be developed, it just don’t add up. They’re going to have to build on everything. The people coming in don’t give a damn about the water or land or anything else.” 

When Billy Davis Jr. talks, younger generations of Florida cowboys listen

When Billy Davis Jr. talks, younger generations of Florida cowboys listen.

Davis wasn’t the only one who didn’t feel great about the future. After a while, you could become a little numb to the beauty of the country and the drive would start to feel funereal. Almost everyone acknowledged at some point that this kind of Florida won’t last much longer. All the young cowboys I spoke with told me they’d likely have to head west to find work. 

“I could feel a dirge,” Yarborough told me. “We’re losing land to development with all the Yankees moving down. There’s nowhere left to hunt or fish, you know?” She fears that in spite of their efforts, it’s only a matter of time before the land is covered with shopping malls and houses. “We’re more than just a dadgum mouse and Shamu,” she said. “But I don’t know if we will be able to have another cattle drive like this one. It’s getting hard and harder to find contiguous land.”

Ranchers happen to be some of the most significant conservationists in Florida. Their farms preserve the last open spaces that aren’t owned by the state. But running a ranch is hard, expensive work, and developers are offering ungodly amounts of money. 

Later that evening I talked to one of the young cowboys on the drive. His name is C.W. Yarborough and he’s a 27-year-old, fifth-generation Cracker—a distant cousin of Lynn’s. (I was told that if you holler the name Yarborough in Seminole County someone is sure to answer.) C.W. has been a cowboy since he was 6. “I was on a pony—not quite a Shetland—but a pony and it was older than dirt,” he said. “I swear it was around when Jesus walked the earth.” C.W., his wife Eden and their family own a little more than 1,300 acres where they raise cattle and grow bahiagrass. They are selling the farm. 

“It’s not a decision we take lightly,” Eden said. “Any time you part with a piece of land that holds as much history as this does, it is heartbreaking.” Eden is also sensitive to those who might criticize them for wanting to move on. “There are people who point their finger and say we are making a horrible decision for the environment,” she said. “But if you had a piece of land in the middle of nowhere and then all of a sudden you’re surrounded by subdivisions, it’s no longer the place you grew up.” 

C.W. and Eden don’t think they should have to bear the burden of saving Florida. A lot of pressure is put on ranchers to be our saviors, but our state government doesn’t seem to have much interest in discouraging development. Wherever his family ends up, C.W. still wants to be a cowboy. 

The drive is about what we are losing, but also about what we can save.

The drive is about what we are losing, but also about what we can save.

I eventually earned a nickname—“Cowboy Without a Wedding Ring”—and the teasing stopped, too. I grew into a confident rider and didn’t make too many mistakes. I wouldn’t have fooled Billy Davis Jr., but the untrained eye might have me mistaken for the real deal. 

By Saturday afternoon, we had passed through more than 80 miles of Florida and yonder was our end destination—the Silver Springs arena where we would enter, single file, to a small, cheering crowd like returning conquerors. 

It no longer felt like a funeral march. We were celebrating what we just saw. The drive is about what we are losing, but also about what we can save. Florida will change. It always has. And to think we can stop the march of time is folly. But we can remember. Everything dies, but for something not to be remembered is for it to die twice. 

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