The annual Florida Cracker Trail Ride starts again on February 14. As their website explains, the week long ride re-enacts when cracker cowboys made the “return trip from Bradenton on the west coast back to Fort Pierce on the east coast after cattle herds were safely on their way to Havana.”
Many of these images include members of the Park family who regularly participate in the ride. They are a Truly Florida post in and of themselves but, put simply, their kindness and generosity allowed me the opportunity to photograph a few of these rides and I can’t be more grateful. They gave me the opportunity to see more of Florida than most have or will.
The ride is dirty, sometimes hot and other times freezing and if you aren’t a skilled horseman or woman, you have no business on the ride. But despite a bucking horse (or more) and despite the half inch of dirt caked on your skin within a day of the ride, it is one of the most inspiring experiences one can have. I wish all the riders a great time this year and thank them for keeping history alive.
In the first morning light, Josh Kimtowicz, 18, of Englewood, prepares horses for the first leg of the 21st Annual Florida Cracker Trail Ride.
Suzanne Park drives Karl, a nine-year-old standardbred gelding, out onto the trail from Kibler Ranch to start the first leg of the trip.
Horses take a water break at a stop along State Road 64 between Kibler Ranch and Bar Crescent S Ranch. Ranches and farms along the trail generously offer their land to the riders for breaks.
 
Clarence Polston, left, and Chad Holding sit back and watch the Daytona 500 on the Bar Crescent S Ranch after the ride from the Kibler Ranch in west Manatee County. This was Polston’s eighteenth year and Holding’s first year riding the trail.
After completing the first leg of the trip, Jaden Park, 19 months, gets a bath in a cleaned horse’s water bucket on Bar Crescent S Ranch.
E. O. Koch and Vicky Baldwin dance to music by Roger Brutis of Wauchula near a cross lit with tiny lights on Bar Crescent S Ranch Every night of the ride there is a form of entertainment for the riders.
Lights from the inside of motor homes dot the Bar Crescent S Ranch under a cloudless star-filled night.
Florida Cracker Trail riders leave the Bar Crescent S Ranch in Hardee County.
Riders take the final steps to the Atlantic Ocean where the horses can cool off.
Calvin Pugh takes his horse into the Atlantic Ocean off Frederick Douglas Park in Fort Pierce after completing the 21st Annual Florida Cracker Trail Ride.
Written & photographed by Molly Dempsey
February 13, 2015 at 7:43 pm
Awesome! Very well done Molly! Love it!
February 16, 2015 at 1:49 pm
Super collection of photos…I have ridden for many years but have missed the last two by necessity…It is a great piece of history brought to life……
February 22, 2015 at 8:02 am
Beautiful photography! Just finished the ride myself and this tells the story!