Our Team
Kathy Dewar
Owner/Head Trainer
(262)-488-8286
Kathy grew up in Wisconsin and when Laura Kraut moved there, Kathy took the opportunity to train with her. While under her guidance, Kathy trained at a high level with her show jumpers and hunters that she brought along to sell. Kathy has had a very successful career, with some of her accolades including wins in the 1.45 classes at Indoors, numerous Grand Prix wins, and experience up to the 1.55 level. When Kathy moved out on her own, she purchased her second thoroughbred, 'McGrath'; together they won their first Welcome Stake and Grand Prix in the same weekend. The winning chestnut was the motivation to start her own farm 'Chestnut Hill'; named in his honor. The farm opened originally in Wisconsin, but then relocated to Ocala for a more central location for Kyle and Kathy's two children to grow up.
Kathy's best Grand Prix horse to date, Spitfire, was purchased through Kyle's connection with Bruce. They had a long and illustrious career together, winning over 10 Grand Prix classes. Bruce's mentorship and connections are still a vital aspect of Chestnut Hill farm today, as Kyle and Kathy meet him in Europe several times a year to import horses for clients and sales. Kathy enjoys sharing the love of horses and competing with her daughter Ada and supporting her son Jackson's highly esteemed Rocket Club, along with his passion for fishing, tennis, and golf.
Kyle Dewar
Owner/Head Trainer
(352)-286-6880
Kyle grew up in Calgary Alberta, watching the famed Spruces Meadows. As a junior rider he won the high point junior rider scholarship at Spruce Meadows; compiling many great wins on ponies and horses. At 15, he was lucky enough to go to Ireland to train and ride with the great Eddy Macken for the summer. At 17, Kyle moved to Belgium to work for European Sport Horses, a high volume sales barn. He moved back to Canada in 2001 to compete in the North American Young Riders Championship where he earned a Silver Medal. Following that championship, he worked for Bruce Goodin’s stable in Sweden. Bruce is a 5 time Olympian and a great mentor and teacher, who Kyle still works closely with today. Following his time with Bruce, Kyle moved to the United States in 2005 to work for Aaron Vale, which is when he met his wife, Kathy. They soon opened Chestnut Hill Farm together.
Some of Kyle’s many accomplishments have been Leading Money won Canadian Grand Prix rider, along with many Grand Prix wins nationally and internationally. Kyle enjoys running a family focused operation, with his daughter competing at a high level, along with the farm being host for his son's international rocket club.
Annie Bolling
Assistant Trainer
(251)-423-1858
Annie grew up in Alabama under the tutelage of Holly Shepherd. As a junior she competed at Indoors in both the hunters and jumpers. Annie competed in her first Grand Prix at just 17, and then went to college at the University of Alabama where she earned a Business Management degree. While in college she started riding and training professionally, and purchased her current Grand Prix horse 'Mykonos SCF'. After college, Annie worked for a private family where her clients earned top ribbons at Pony Finals, Capital Challenge, Harrisburg, and Washington. During that time Annie was fortunate enough to be mentored by Ali Sweetnam.
Annie was both team and individual gold at the 2023 USHJA Platinum 1.45 Jumper Championships and has had several welcome and grand prix wins. She has also had success in the FEI U25 series at the Winter Equestrian Festival.