On a cool March morning in Immokalee, the light comes slow and pearled over the palmettos, turning the John Jimmie Memorial Arena into a shallow bowl of mist. Trucks idle in a loose ring, saddles creak and spurs give off a faint, familiar jingle.
By 8 a.m., the cowboys have begun to gather for the annual Immokalee Cattle Drive and Jamboree. At the group’s center is fourth‑generation cattle rancher Heather Cleckler, great‑granddaughter of Robert Roberts, a pioneer of the South Florida frontier and one of the first to establish a cattle empire in Immokalee. She is the drive’s cattle boss, a living link between what this place once was and what it’s trying to remain.
In a pearl‑snap shirt and well‑worn boots, she scans the growing knot of cow folk, horses, cow dogs and cattle. “Y’all eat,” Heather calls, nodding toward folding tables where biscuits, eggs and bacon steam in aluminum pans. “You can’t chase cows on an empty stomach.”
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Photography by Anna Nguyen
immokalee cattle drive heather cleckler loads up horses
Since 2022, fourth-generation cattle rancher Heather Cleckler has helmed the Immokalee Cattle Drive and Jamboree, a nine-year tradition with a more than 500-year legacy. Top photo: Heather and her father, Pat Howell, corral a herd with family ranch manager Johnny Summerall.
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Photography by Anna Nguyen
immokalee cattle drive horse harnesses on the wall
The late-March drive is, on paper, a one‑day heritage festival, but to the people who ride it, it is a working memory with a permit. The event honors over 500 years of cattle in Florida, America’s first cow state, beginning with the livestock brought in 1521 by Spanish settlers, whose language clung to saddles and ropes. Those early herds laid the groundwork for vaquero traditions that would influence the American cowboy. After the Spanish left, the Seminoles were the first to rustle up the loose steer, before Cracker pioneers arrived, their whips cracking so loudly the sound gave them their name.
Heather’s mare is waiting by the cow pens. She is sun‑brown, more tendon than show, with the look of an animal that’s learned this heat and made its peace with it. Ahead, Florida Cracker cattle mill in the gray light, a swirl of brown and white with horns curving toward the earth. “Alright, let’s talk to ’em,” Heather says. Her father, Pat, works the left flank, low and steady. On the other side, a whistle from her mother, Karen, cuts sharp and high. Another call rises from rancher Moses Jumper Jr., a fourth‑generation Seminole cowboy, who is being honored at the drive for his family’s legacy in the trade. His grandmother, Ada Tiger, worked cattle around the same time as Heather’s great‑grandfather. Old‑timers along Lake Okeechobee remember seeing her appear like a weather front, one woman, two dogs and a string of cattle that did exactly what she asked of them.
Outside the gate, Heather’s 86‑year‑old uncle, Dallas, the drive’s grand marshal, pops his tongue against his teeth in a sharp, hollow click‑click‑click. Heather listens, then adds her own, a long and rolling call, starting in her chest, then spilling out smooth. The dogs catch the mood and chime in with short, urgent barks. “Listen to that,” Karen calls, half‑laughing, half‑breathless. “We’re gonna need a band name before long.” Heather smiles: “It’s just a cow song.”
Photography by Anna Nguyen
immokalee cattle drive heather cleckler and sons
With roughly 100 cattle and 40 riders moving through downtown Immokalee and thousands of spectators, the drive celebrates the culture while underscoring industry’s role in the region. Cattle ranches hold some of the last large, unbroken stretches of green space, filtering water, providing shelter for wildlife and absorbing stormwater. “We’re taking care of the land, so it can take care of everybody else,” Heather says.
In a state that changes its face by the season, the Roberts, Jumpers and other cattle families of Southwest Florida stand as a living, breathing answer to a question Florida keeps asking itself: What do we keep, when keeping is hard?
Cattle ranches hold some of the last big, unbroken pieces of green on the Florida map. Their pastures filter water that seeps south to the Everglades. Their cypresses shelter birds, panthers and deer. Their low, open horizons give stormwater a place to go when the summer rains hammer down. “We’re taking care of the land, so it can take care of everybody else,” Heather says.
The first official drive took place in 2017, with about 30 riders and a borrowed herd moving 3 miles through town to the Immokalee Pioneer Museum at Roberts Ranch, the site of her family’s original homestead and where the parade ends with a multicultural jamboree. The event has run every spring thereafter. Now roughly 100 cattle and 40 riders make the trek, drawing thousands of onlookers to a town of about 25,000.
The Cattle Drive is a living reminder of Southwest Florida’s Roots.” — Gulfshore Life Community Advisory Board Chair, Denise Cobb
Photography by Anna Nguyen
immokalee cattle drive cattle being loaded up
Heather, who has helmed the procession since 2022, was eager to preserve her home’s history and culture when she raced from a degree in education and the life it offered, back home to cow pens, flatlands and the call to feed those who fed her. Last year, she introduced the Immokalee Cattle Drive Scholarship Pageant, which provides mentorship and educational funding for local girls and honors the women who ditched the covered wagon for a saddle and stirrups. “Immokalee was built by women with grit,” she says.
When Robert Roberts brought 300 head of cattle to this scrubland, he began what would become a 100,000-acre operation. Today, a fraction remains. The decline of ranchland in Southwest Florida began in 1949, when a statewide fence law ended open-range grazing and forced cattle off public roads, breaking up land that had once functioned as a continuous, working landscape. As development followed, locals started calling to protect large swaths. Portions became the Florida Panther National Wildlife Refuge and Big Cypress National Preserve; others were protected through a 2001 state program that buys development rights while allowing ranchers to keep working the land.
Heather and her parents now run a smaller, more intricate quilt: a cow-calf operation with a permanent herd of mother cows weaning healthy young cattle. Most are sold in lots through regional sale barns or direct to order buyers, eventually disappearing into the broad anonymity of the national beef supply. Somewhere behind the bright lights of a supermarket meat case in Tampa or Chicago, a label reads “Product of USA,” and Heather’s work is folded into it like the ribbon of marbled fat threading its center.
Photography by Anna Nguyen
immokalee cattle drive heather and her mother karen
Heather and her mother, Karen, prepare for the parade.
Nearby, Seminole families have built cattle operations in Big Cypress for generations, working with the hardy Florida Cracker breed, which evolved from the Spanish herds. Formalized in the mid-1930s, the program now runs tens of thousands of head—one of Florida’s largest cow–calf operations—funding both families and tribal programs. “We don’t just raise beef,” Moses says. “We raise our own ground to stand on.” Heather turns slightly in the saddle, watching the line hold as the cattle settle.
From the outside, Florida’s cattle country can look like a postcard of permanence with cows grazing under live oaks, herons stalking ditches and fence lines stretching out to the horizon. But a cluster of pressures is tightening year by year.
“I ain’t scared of a hard year,” Heather’s father, Pat, says softly. “I’ve had plenty. What scares me is that it’s ending with me. Not the land. The land will always be something. Houses, swamp, weeds, whatever. But this way of doing it, seeing Heather pick it up,” his voice trails as he wipes his thumb across his cheek. “That’s what gets me.”
Photography by Anna Nguyen
immokalee cattle drive cattle drive within the street
Heather is part cattle boss, part conservationist, part economist and all mother, raising a fifth generation to love a life that is getting harder to justify on paper. The pressure starts with the land—coveted by developers, strained by rising taxes—a grazing pasture at the crux of an operation that can, with a single offer from a subdivision builder, become an irresistible temptation for neighbors already stretched to the breaking point.
Then there is the weather, erratic where it used to be merely difficult. Too much rain in the wrong month, and calves grow weak on sour grass. Too little, and ponds shrink to cracked bowls, cattle bawling at dry water holes. And then the market: feed prices climbing, beef prices swinging, the heavy, grinding math of a business built on living creatures and time. “The cattle don’t know about interest rates,” Heather says. “They just know when the grass is good and when it’s not.”
By mid-morning, the cattle start moving toward Main Street. Somebody near the tortilleria shades his eyes and says, almost to himself, “Aquí vienen,” or here they come. As it approaches, the herd folds its past and present into the same frame.
Photography by Anna Nguyen
immokalee cattle drive josh jumper
Josh Jumper enjoys the 2025 Immokalee Cattle Drive. His father, fourth-generation Seminole cowboy, Moses Jumper Jr., was honored at last year’s event. Their family ranch contributes to one of the state’s largest cow-calf operations.
The majority of the population in Immokalee—which takes its name from a Miccosukee word often translated as ‘my home’—is Latino, with large communities from Mexico and Guatemala, and significant Seminole and Black populations, including Haitian families who have followed the crops north and south for decades. Once, Immokalee’s main employers were cattle and timber, now citrus and vegetables. Ranching may have moved to the edges, but it still lies just there beyond the streetlights.
The two economies meet daily at the same gas pumps and grocery aisles. Today, on Main Street, amid hand-scrawled “WE FEED AMERICA” signs, a swirl of copper-colored cattle passes by—a reminder that this little town, wedged between swamp and subdivision, still makes its living and finds its meaning in coaxing food out of thin, sandy soil and heat-tolerant hide.
Lining the sidewalks, men in ball caps with farm logos, women in long sleeves despite the heat, children sticky with paleta juice, ranching families from one end of the region to the other, visitors and locals stand eager to learn and to remember. The cows move forward in a slow, shifting line, hooves sparking the broken asphalt, leaving round, muddy signatures that will dry into dark rosettes.
Cowboys and cowgirls are not just in children’s stories or westerns, they are real people here.” — Community Advisory Board Member, Architect David Corban
Photography by Anna Nguyen
immokalee cattle drive heathers father outside horse trailer
From the outside, Florida’s cattle country can read as a postcard. On the ground, it’s a business shaped by development pressure, shifting weather and tight margins. It’s a family effort, including her father (pictured here), along with husband, Randall, and daughter Sherri Grace. “If we want to save anything of this state’s soul, we’d better start with the people who still walk it on foot and horseback,” she says.
On horseback, Seminole riders in bright patchwork shirts ride alongside Florida Cracker cowmen in sweat‑stained straw hats, alongside brown‑skinned vaqueros whose grandfathers crossed different borders and found the same sun. Mexican and Seminole women dressed in traditional garb, soon to dance in the old way on the Cattle Drive stage, ride in open buggies. Young girls wave Seminole and Florida flags while babies ride easy in the saddle between their mamas and daddies. One little boy’s boots are scuffed and dusty, but his belt buckle shines like a small moon.
The cattle drive queen rides near the front, her sash a diagonal cut of pearl. A girl in the crowd, no more than 8, leans forward as if the sight might pull her out of her shoes, her mother’s fingers resting lightly on her shoulder. The cattle float past the taqueria, past the tienda where wire transfers fly north and south each Friday. A steer balks at a shimmer of rhinestone, a buckle fallen loose in the road. Heather eases her horse alongside, speaking softly, in cow song.
Photography by Anna Nguyen
immokalee cattle drive sunrise people on horses
Her three children ride beside her now, small boots in big stirrups, faces intent as they help push a group of cows past one median then another. To them, this doesn’t yet feel like an endangered way of living. It’s just home. “If we want to save anything of this state’s soul, we’d better start with the people who still walk it on foot and horseback. The men and women feeding us here at home and across the country,” she says.
When the last cow’s tail flicks out of sight, the crowd loosens. People make their way to the Pioneer Museum for a proper party. The past slips back out of view, but something lingers. For the length of a cattle drive, the story of who feeds whom, and who is seen and who is not, has stepped out into the open and walked right down Main Street. The song has changed languages over the centuries, but the feeling is the same. Earth turned and turned again, bodies tired and rising anyway, animals moved from one pasture to another, and finally from pasture to plate.
Photography by Anna Nguyen