When David Hunt, Great Florida Cattle Drive “Boss Boss,” and Jack Gillen, another member of the Drive organizing team and a “cow hunter” himself, reached out to me several months before the Great Florida Cattle Drive of 2026 and asked to be guests of mine on the Horse Talk Show, I was very interested in what they had to say. It sounded like my kind of adventure, crossing Florida on horseback, camping and moving cattle. I was very interested in experiencing it myself. My horse was injured last year and has been recovering from a fractured hock, so it did not seem possible to me immediately, until Jack offered a horse to me to be part of the media team and bring additional coverage and exposure to the Drive. After some thought and some weeks passing, I felt the desire to take the time off work and learn more by being involved in this experience.
I was a big John Wayne fan as a child in England and watched hours of his Western movies with my dad. I always imagined if I ever did anything like this, it would be out West, but now here I was planning to go from Yeehaw Junction to the Okeechobee Cattlemen’s Arena on a horse with cattle and camping, right here in my now home state, Florida. Friends I already ride with at Misty Morning Hounds were also booking their adventure to go along, so it seemed to be a perfect plan.
I did not know what I was in for until the first morning, packing up a tent at 5 a.m. in the dark and trying to move gear across camp to a trailer to be transported to the next campsite, while also trying to ready a horse I was not familiar with. It was a lot and a bit overwhelming for a “newbie” to begin with. After I got into the routine and the swing of things, I was loving it all. A ride on a Florida Cracker Horse and a ride-along with Marilyn Whitford on her wagon with her mules, Tom and Ted, was a perfect way to capture the best footage.
I also had the opportunity to meet an incredible lady representing the Seminole Tribe, Wendi Riley. I was alongside to witness Wendi speaking to the livestream going out to all fourth-graders in Florida, providing an opportunity for them to learn, live on air and vicariously, about Florida’s cattle heritage. I was surprised to learn about the huge part that the Seminole Tribe has played in Florida’s cattle heritage and the present-day role they play in the agriculture of Florida. I also had a chance to meet so many horse owners with a slew of breeds, from a variety of different disciplines and all ages, from young children to seniors. I discovered many familiar faces and friends were also there for this experience. Some rode English, others very Western, some had attended the last Drive in 2022 and some had even attended the very first one in 1995.
The Great Florida Cattle Drive was created in 1995 to celebrate Florida’s 150th birthday and happens about every five years. I also had a marvelous opportunity to meet Carlton Ward and interview him. Ward brings together people with wildlife, water and conservation through his photography and advocacy. To quote the website, “The Great Florida Cattle Drive is more than just a trail ride; it’s hundreds of riders coming together participating in a living history experience that celebrates Florida’s cattle-driving traditions.”
We covered almost 80 miles in this weeklong adventure, moving cattle across some of Florida’s remaining ranchlands. We crossed 16 ranches and learned about the challenges and triumphs faced by early Florida cow hunters. This living, breathing reenactment celebrates Florida as one of the first cattle states in America.
It got really cold for several nights while we were camping and, as I squeezed into my tiny tent and slipped into my sleeping bag, I wrapped my wool blanket around myself to try to stay warm. The tent was sold to me as waterproof, but not ice-proof, apparently. It was very cold. I had zero regrets and would do it again tomorrow. I met some of the most incredible, gritty people dedicated to conserving the land and keeping alive the legacy and traditions of Florida. I immersed myself in the lifestyle, eating chuckwagon meals, listening to cowboy poets and stories of days gone by and dancing with the Seminole Tribe, participating in the Stomp Dance around a huge fire.
This unique event offers an authentic glimpse into the life of 19th-century cow hunters, allowing riders to cross the state’s beautiful, unspoiled landscapes while driving cattle, much like the pioneers did centuries ago, and I cannot wait to sign up for the next one.
The Great Florida Cattle Drive is not for the faint of heart and it is challenging at times, but worth every minute spent. It is not a trail ride. It is worth digging much deeper than that. The Great Florida Cattle Drive is an expedition designed to replicate the experiences of Florida’s original cow hunters. Don’t miss out on the next one. Stay tuned…
