United States Eventing Association

Caitlin Silliman: The Roller Coaster World of Eventing

This article originally appeared in the April 2024 Eventing Issue of Sidelines Magazine.

As both an eventer and business owner, Caitlin Silliman is well aware of the need for a solid team behind her. Not only has she had supportive family and friends cheering her on, she has ridden and worked under top-notch professionals such as Susie Beale and Silva and Boyd Martin, and now runs her business side by side with her good friend and fellow eventer Erin Kanara at Erin’s farm in Pennsylvania, the state Caitlin has always called home.

It all started with six riding lessons for her 6th birthday. “My mom rode as a kid, and her mom rode as a kid,” Caitlin said. “So the horse bug was in the family, but no one rode competitively.” Once she started lessons with Susie Beale at Cairn O’Mount Stables in Malvern, Pennsylvania, she never stopped.

“I grew up riding with Susie and she got me through the Intermediate level. I didn’t have a horse of my own until I was 15, but Susie always made sure I had a horse to ride and compete consistently,” Caitlin said. “I did Young Riders in 2006, achieving team and individual bronze, and was exposed to other riders that were working students for top professionals like Phillip Dutton and Kim Severson. Young Riders gave me the first taste of team competition, between the training camps leading up to it and the actual competition, and it showed me that becoming a working student was the next step in having a career in eventing and making my way toward the top level of the sport.”

The summer of 2007, after Caitlin’s Young Riders experience, Boyd Martin had just moved to the U.S. and was working for Phillip Dutton. Susie rode with Phillip and would take Caitlin to watch her jump lessons. This was Caitlin’s first introduction to the Martins, and the beginning of a wonderful friendship. During Caitlin’s senior year of high school, she took a lesson with Silva to work on getting her horse on the bit. After the first lesson, Silva suggested she leave her horse for two weeks of training. This was out of Caitlin’s budget at the time, so she asked if she could work it off, and Silva agreed. Two weeks later, Silva asked Caitlin what her plan was for the future.

“The deal with my parents was that I could take a year off to work and ride, but I had to apply to college,” Caitlin said. “I had already applied and was set to go to the University of Delaware, which was close by, and I was planning to keep my horse at the farm near the Martins’ and go to school while working off lessons and board. That is, until Silva offered me a job—that was it, I never left. I deferred from college for a year and then I just stayed with Boyd and Silva.”

Working for the Martins turned out to be the best education Caitlin could ask for. What she learned while watching them grow their business, Windurra USA, from the ground up was invaluable. “For a while, we joked that I went to Windurra University, which turned into a Windurra master’s degree because I spent the next eight years there,” Caitlin recalls. “Obviously they have an unbelievable business now and they’re both hugely successful. I got to be a part of all of that. They have really helped me in every aspect of my career.”

Ups and Downs

When it comes to the roller coaster of eventing, Caitlin has definitely experienced some mountains and valleys. In 2011, just after she was short-listed for the Pan American Games in Guadalajara with her horse Catch A Star, the unthinkable happened: the True Prospect Farm barn fire. Boyd Martin’s barn was destroyed, six horses were lost to the fire and more were injured, including Catch A Star. “The barn fire is something I never thought would happen to me or any of my friends,” Caitlin said. “You see barn fires in movies like ‘The Black Stallion,’ and you look at things as fire hazards, but I never imagined it was something that would happen to me. Having to overcome that, my horse and horses we cared for being injured, and most of all, losing the six we couldn’t save, was a horrible experience.”

With Caitlin’s watchful care, along with vet Dr. Kevin Keane and the team of vets that cared for Catch A Star at the New Bolton Center, the mare made a full recovery and went back to competing. Caitlin and Catch A Star beat the odds together with some incredible finishes and worked their way up the levels, including a top-five finish at Bromont Horse Trials CCI4* in Quebec, Canada, just a year after the fire. But just as they were finding their groove again, Caitlin was badly injured while riding a horse in the dressage arena. The horse tripped and Caitlin fell, hitting her head just below her helmet on the edge of the arena, resulting in a traumatic brain injury.

Caitlin lost all her fine motor skills and was admitted to the ICU, and then inpatient rehab for two weeks. Caitlin didn’t give up. “The way I’m wired, I knew I would come back from it and ride again,” she said. “But as a 21-year-old, having to learn how to walk again is a bit humbling.” Even then, she credits her team with her successful comeback from both events.

“I have to give my parents a huge amount of credit for never trying to talk me out of riding after the accident,” she said. “I’m sure it’s not easy seeing your child in the ICU, but they never once suggested that I take a step back from my dream of riding at the five-star level. Boyd and Silva were conscious of being careful with my return to riding and we started out slow, but they kept Catch A Star going the entire time during my recovery and got me to my first five-star at Kentucky the following April.”

Five-Star Debut

Even after two catastrophic events, Caitlin kept working hard to reach her goals and achieved her five-star debut in 2013 at the Kentucky Three-Day Event aboard Catch A Star, just months after the head injury. One week later, Caitlin won the CCI3* at Jersey Fresh International aboard Remington XXV. She also had a big finish at the Fair Hill International CCI3* in 2014. “It was the first time I was in the top three with Boyd, my coach,” Caitlin said. “Those were pretty special.”

Caitlin later retired Catch A Star in 2016 after a fantastic career and she now enjoys her much-deserved retirement among the rolling hills at a friend’s Pennsylvania farm. “They told me they weren’t sure if I’d ever ride Catch A Star again at the same level after her skin was so damaged in the fire,” Caitlin said. “She gave me my first five-star. That was unbelievable, and something I wasn’t sure was achievable for us, but she made it very achievable.”

After working and riding under the Martins for eight years, Caitlin decided it was time to take a big step and go out on her own. She started her own business in January 2016. “It was so hard! I would have stayed there forever,” Caitlin said. “Boyd and Silva were so good to me. But at some point, I wanted to have a business of my own like they have, and it was never going to be ‘the right time.’ So I just got this itch where I felt like it was time to give it a go on my own.”

Caitlin started working in Aiken, South Carolina, where she was already a familiar face, having come to the area every winter since she was a child. She started small, driving around Aiken to ride and teach whenever and wherever she could, building a name and reputation for herself and her business. “I learned so much from Boyd and Silva, but the main thing is that they’re the hardest workers I know. And that was one thing I knew how to do: keep my head down and work as hard as I could for it,” Caitlin said. “It seems like it was just yesterday that I was in the barn with just two horses, panicking about buying hay and paying rent, and now I’ve got a barn full of them and can only take so many.”

On Her Own

After owning her own business for almost eight years, Caitlin hasn’t forgotten how important it is to be part of a good team. It takes a team to run a training and eventing barn, which is why she enjoys running her business from her friend Erin Sylvester Kanara’s farm, enabling them to work together to make it all happen. “We have Boyd Martin three miles to the right and Phillip Dutton three miles to the left,” she said. “We both run our businesses out of separate barns on her property. If one of us is away, we ride each other’s horses or help each other’s students. We also both train with Boyd, so we have a very similar style. We’re able to help each other out on young horses and often take lessons together.”

Caitlin credits much of her current success to being able to work with and lean on Erin. The support of her team has been especially important since the loss of her best friend, Annie Goodwin, who was killed in a tragic riding accident in July of 2021. “I thought about quitting, but I knew Annie wouldn’t want me to,” Caitlin said. “The grief I’m still struggling with daily and the pain of watching her family, fiancé and friends struggling with her loss is something I would never want my family to go through.”

Despite the grief from the loss of Annie, Caitlin’s passion for the sport and her drive to reach her goals keeps her eyes on what comes next. Even though she is a trainer herself and has reached the five-star level, she still has big dreams to achieve and continues to be a lifelong learner. “If it were an easy sport, everyone would be going to the Olympics,” she said. “But that’s what makes success that much sweeter. And like with every sport, if you want to be the best, you can’t ever stop being a student. You have to keep training with the best professionals and learning.”

Caitlin has high hopes for her current top mount, her Advanced-level horse Ally KGO, a Trakehner mare. “I’m chomping at the bit to have her back out going Advanced and I really do think she’s a five-star horse. I want to get back to the top level,” Caitlin said.

With her sights set on senior teams like World Championships, Pan-Ams and the Olympics, Caitlin looks forward to bigger and better things while continuing to train, coach and mentor her current group of college students and their horses who call her barn home. With her team behind her, the sky is the limit as she looks to the future. "I have such a great group of people cheering me on,” she said. “I think my barn has a reputation of being a great team where we all support each other. That’s one of the big ingredients of making it to the top: the support system around you.