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Callaway Saylors LLC

About Us

Meet The Owners

Callaway Saylors rider jumping a bay hunter over a stone-pillar fence

Kevin Callaway

Hunter/Jumper

Kevin Callaway’s passion for horses began in middle school at a local lesson barn in Atlanta, Georgia. What started as a hobby quickly grew into a lifelong commitment to horsemanship, training, and the sport of show jumping.

Kevin got his first horse—a 15hh Quarter Horse gifted by a family friend—and trained him himself all the way to the 1.10m jumpers. This early experience sparked a drive to learn every aspect of horse care, training, and competition.

In 2017, Kevin devoted himself full-time to the equestrian industry, working for an A-rated show barn and gaining invaluable hands-on experience. He later joined the team at Windsor Stables under Michael Britt-Leon, where he received top-level training and traveled to AA-rated shows, further refining his skills both in and out of the ring.

Following his time at Windsor, Kevin launched his own lesson and sales program in 2023 in Athens, Georgia. There, he specialized in developing unstarted or green ponies and horses into safe, quality show prospects suited for junior and amateur riders. He has experience competing in the 3’3” hunters and up to the 1.20m jumpers.

In January 2024, Kevin combined his program with Garrett Saylors to establish a full-service training, sales, and show program. In 2026 the partnership moved its program to Ocala, Florida. His long-term competitive goal is to advance into the 1.45m+ Grand Prix jumper divisions while continuing to help horses and riders progress with confidence and strong foundations.

Callaway Saylors rider cantering a black dressage horse in a show arena

Garrett Saylors

Dressage Trainer/Owner
Garrett Saylors began his equestrian journey as a hunter/jumper rider in 2012 and discovered his passion for dressage in 2018. By 2020, he was working with young horses under the guidance of Derek Peterson in Gainesville, Florida, honing his skills and deepening his understanding of training foundations. Garrett then spent two years with CDI rider and trainer Charlotte Osborne, gaining invaluable experience at the highest levels of the sport. Following this, he founded Saylors Dressage, focusing on developing horses and riders through thoughtful, high-level training. More recently, Garrett combined forces with Kevin Callaway in 2024 to create Callaway Saylors LLC, and in 2026 the two brought their program to Ocala, returning Garrett to the Florida horse community where he first trained young horses.

Where We Train

Callaway Saylors is based in Ocala and serves horses and riders throughout Marion County and the surrounding area. Because our program is built around training and coaching, we come to you: we ride and teach at the barn where your horse is kept, and we coach at local schooling shows, rated competitions, and the major Ocala venues during the winter season.

Not sure whether we can reach your barn? Contact us and we will let you know.

Kevin & Garrett

Kevin Callaway and Garrett Saylors standing in a barn aisle with their dogs