Family Focus

It was a rainy and muggy morning, but Kathy and Kyle were where they often are, at the barn. Kathy and Kyle Dewar are the owners of Chestnut Hill Farm and are one of the increasing numbers of couples and families that compete at horse shows all across North America. They met through a mutual friend almost 8 years ago and have been happily married and competing, sometimes against one another, for blue ribbons ever since.
Kathy is originally from Wisconsin and started riding at age 10. At 13, she used her babysitting money to pay half the purchase cost of her first horse. She started off riding western but discovered that to ride through the long Wisconsin winters she would need to ride the hunter/jumpers as they had the indoor rings. Thus began her life as a hunter/jumper. Kathy was fortunate enough to have Olympian Laura Kraut as a trainer, giving Kathy the opportunity to ride some of the top horses in the country. When asked, Laura said, “Kathy was a fantastic student with a strong work ethic, who listened and tried to do whatever she was told. This is rare”
Originally from Calgary, Kyle was bitten by the horse bug at the age of 6 when he saw Ian Millar win the du Maurier. His mother often worked as a show secretary to pay for his entry fees and he would muck stalls to cover the trainer costs. At 17, he moved to Belgium and worked as a groom and exercise rider.
Chestnut Hill trains and sells hunters, jumpers and equitation horses. They average 14 to 18 horses in the barn at any given time mostly owned by Kathy and Kyle.
They state they enjoy having a great group of clients, and believe that owning a small barn allows them to keep focused on their goals. They own 2 other farms, 1 in Wisconsin and the other in Lexington that is currently being leased out by Nicki Simpson, Denise Wilson, and Sandra Dalman. The Dewar family made the move to Ocala when they decided that raising their 2 children, Ada and Jackson, things would be easier for the children and it would allow them to ride in a more competitive scene.
Kathy and Kyle don’t focus or get upset over which one bests the other in head to head competition, although they may tease each other. The goal at Chestnut Hill is always for one of them to take home the blue ribbon. This allows them to continue focusing on the quality and health of their horses.
Kyle’s a big believer in Hackabits and sometimes a double bridle. He thinks that FEI rules should be the basis for shows and that all horses should be drug tested and jogged before competition to show any soundness issues.
Both professional riders, and Kyle would like to compete on the Canadian team in either the Pan Am games or a Nations Cup. Kathy believes that “…it’s important, when competing against someone you are close to, that you go into the ring planning to do the best you can on your horse. It always takes some of my focus off of my own horses, because I want to pay attention to what Kyle is doing, but I do my best to focus on my class/horse and hope that we can both make it to the jump off to cheer each other on. I always appreciate, if I haven’t had the best class or haven’t made it to the jump off, being able to stand at the rail and watch him jump off. It’s like having a shot at the win without being in the jump off.” She would like to spend more time getting their children going on their pony. This summer spent at Fox Lea, Ada and Jackson have done the lead line classes and it has helped get them excited to ride.  Although they want to encourage the children to follow in their footsteps as horse
riders, they won’t push. Kathy would like to find a balance of showing and developing her horses as well as spending as much time with their children as possible.
The Dewar’s believe family is core and take the children and grandparents with them when they compete out of town. They are enjoying the friendly family
environment at Fox Lea and have said they will be showing here again and look forward to it.
The Dewar’s would like to thank CWD Saddles, Sam Shields, and Choice of Champions for their support in Chestnut Hill Farm and the Dewar Family. I would like to thank the Kathy and Kyle for sharing their time with me and giving me the opportunity to get to know them a little better.
To learn more about Chestnut Hill Farm and the services they provide please visit

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