Riders on the Cracker trail. (Photo courtesy of Jerri Phillips)

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More than 100 years ago, bands of Cracker cowboys gathered free-roaming herds of cattle and drove them some 140 miles along the so-called Cracker Trail west from Fort Pierce on Florida’s Atlantic Coast to destinations at Bradenton, Tampa, Punta Gorda and Punta Rassa on the state’s Gulf Coast for shipment to Cuba. 

These days, Florida’s rural landscape is diminishing and the Cracker cowboys – named for the cracking sound of their whips – are long gone. But a group of Floridians aims to make sure their legacy is never forgotten by annually following the Cracker Trail across the state in one of the most arduous trail rides ever undertaken. 

“Land in Florida is disappearing,” said artist and equestrian Jerri Phillips. “I became fascinated with Florida’s history and I wanted to experience it – the Cross State ride is one way to keep Florida’s history alive.”

The brain-child of the Florida Cracker Trail Association, the first Annual Cross State Ride stepped off in 1987, and every year since has begun at the Manatee Historical Park in Bradenton and traveled west 120-miles over eight days to Fort Pierce, where the trail riders are the center piece of that city’s Heritage Festival. 

Over the course of the route, riders accompanied by outriders and drivers of wagons containing food and camping equipment cover an average of 20-miles a day, taking lunch and water breaks, before they make their evening camp at participating ranches along with way.

“And it’s not just riders,” said Kathy Wolfe, owner of Wolfe’s Born to Ride LLC, leaders of trail riders in Manatee County and a 16-year veteran of the Annual Cross State Ride. “Husbands, wives and children who are not riding follow us driving everything from expensive motor homes to their own cars and trucks, and one year we had a guy who rode a bicycle all the way, and a woman who jugged the trail to call attention to drug addiction.”

In all, more than 100 people take part in the ride every year, according to Florida Cracker Trail Association Secretary Chelsey Knutowicz.

“The oldest rider was 87-years-old and the youngest was 6-years-old,” she said “We’ve had people from all over the country and from Canada who trailer their own horses in for the ride, and we have riders from England, Germany and Italy who lease horses once they arrived here.”

For all who follow it, Wolfe says the trail is demanding.

“This is not a casual trail ride – not the kind where you ride for a couple of hours and go home,” she said. “It’s a tough trip – you have to be in condition and the horse has to be in condition – when the trail boss says you have to leave; when he tells you to keep up, you have to keep up.”

No matter how challenging, Phillips believes that riding trail allows those who follow it to experience Florida’s history in a special way. 

“It’s not just the ride,” she said. “During the ride, there are also kids’ activities that help them learn about the trail, and every night when we camp there are special presentations and social activities – some nights we heard stories from a cowboy poet, another night a member of the Seminole tribe told us stories that his grandmother had told him about Florida’s history.”

There are more personal benefits, too.

“When I finished the trail I got so much self-confidence,” Phillips said. “It taught me how horses react to things, and I met some incredible people along the way.”

Wolfe agrees.

“I have had people say, ‘Oh it’s too hard, it’s too much work’ and it is, but it is worth it,” she says. “At the end of the day I can say, I rode my horse on the Cracker Trail, what have you done?”

In 2000 the Cracker Trail was chosen as a Community Millennium Trail by the White House Millennium Council, a partnership between the White House, the Department of Transportation, Rails-to-Trails Conservancy, and the National Endowment for the Arts. It’s part of a nationwide network of other trails to interpret history and enhance tourism.

Despite the national attention, connecting with the Annual Cross State Ride is not easy, according to Phillips.

“You have to look for it and it’s mostly word-of-mouth,” she said. “But when we ride along highways, people wave at us and honk their horns – they are celebrating Florida’s history, too.”

To learn more about the Florida Cracker Trail Association’s Annual Cross State Ride visit http://floridacrackertrail.org/