Christopher Webb: Hot Horsemen Finds Happiness in Virginia

By Britney Grover

Photos by Shawna Simmons

Though Christopher Webb was born into horses, it was a completely different world from the warmblood hunters of Virginia that now occupy his life. “I’m from Alabama, so I grew up in the Western end of the circuit,” he said. “My mom and dad didn’t compete, they just leisurely rode. Then I met a lady in Alabama who was very proactive in my riding career.”

Carla Shoemaker is a nationally competitive barrel racer whose support changed the course of Christopher’s riding. He became a farrier, and Carla taught him how to break and start young horses. “I moved out when I was about 17,” Christopher remembered. “I finished high school on my own, then I went to college on my own, without my parents’ support. I broke horses and was a farrier, and did the National Barrel Horse Association and International Barrel Racing Association circuits.”

While working with Carla, Christopher also started riding in a “flat saddle” and got hooked. He started actively pursuing English riding, participating in low-level hunter and jumper shows. He was perhaps one of the only cosmetologists to ride and break horses on the side while working in a hair salon, but a difficult breakup made him realize that he wanted more — he was unhappy and something had to change.

Christopher called a friend who worked for Olympic event rider Stephen Bradley over 700 miles away in Middleburg, Virginia. “She said, ‘If I can get you a job, it’s going to involve you moving.’ I was like, Well, I’m only 23 — let’s see what happens.” His friend came through: Christopher got a job with Olympic show jumping rider Ramiro Quintana and moved to Virginia. “I came up here to be a working student and groom, and I never went back.”

When he arrived in Middleburg, Christopher set out to expand his knowledge of the hunter world. “Being from Alabama, there weren’t that many hunter riders that were very good. When I came here to Virginia I really didn’t have a clue,” he admitted, but his fascination helped him learn quickly. “You really just click with something, and for me it’s the old hunters — I love the old-fashioned hunters; the tradition of it and the people here are just so amazing.”

Now Christopher’s 28 and trains horses and clients at Winterfell Farm alongside grand prix rider and hunter breeder Charlie Evaskov — who Christopher says taught him everything he knows about hunters. Co-owner Kristen Cyron breeds warmbloods and Thoroughbred-warmblood crosses, which go off to get started and then Christopher puts the extra training on them and gets them going in the show ring.

Though he’s left his Western riding in the past, his experience with horses has proven universal. “It takes a very special person to be able to break and start young horses, and to just have the mindset to deal with a young horse,” Christopher said. “It takes a special kind of feel, because so many things could go wrong.”

Just like so many things could have gone wrong with leaving his lifelong hometown and moving across the country. But Christopher has finally found where he belongs — where he’s happy. “You know how sometimes you’re born somewhere, and then you move somewhere else and you’re like, ‘This is home.’ I consider Virginia home, for sure.”

And Virginia has brought more than a home to Christopher: It’s brought family. His heart is filled by three rescue dogs: pitbull crosses Jakk and Bruno, and Miss Trixie, a Yorkshire terrier mix. “I got Jakk five years ago at the SPCA in Winchester. I’m not a fan of little dogs, but most of what they had was little dogs. Jakk was the last dog in the kennels. He was sitting there, and I looked at him and he jumped up and put his paws on the door — like ‘I’m picking you,’” Christopher said. “I took him home that day, and he’s been with me, by my side, ever since.”

Christopher and Jakk adopted Bruno as a puppy, and Trixie joined the family just two years ago when Christopher’s big heart saved her from being taken to the pound. “They all go to the horse shows with me; they all stay in one crate together — because that’s how they prefer it, all three in one big crate — and they stay on the road with us. They all three sleep in the bed, and they’re just the best dogs.”

From a competition perspective, Christopher’s goals for the future might not seem ambitious. But his priorities are something that not just horsemen should take to heart. “I never really wanted to be a superstar,” he said, “I always just wanted to be acknowledged and respected in the sport. I think my goal is to just keep going along, keep improving myself and improving the horses, really help the business take off and just enjoy what I’m doing — that’s really the goal, and to keep enjoying it, not get sour and bitter. It’s so easy in this sport to do that. I aspire to be a great horseman, and just try to enjoy life and enjoy what I do, and do it as long as I can.”

Photos by Shawna Simmons, SAS Equine Photography, www.shawnasimmons.com