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Skylar started riding horses at 2 years old. Her mother, Gail Evans was a dressage rider and father, Dr. Joseph Evans, a western rider. Skylar grew up on Emerald Hill Farm in Crozier, Virginia, the Meca of equestrian sport. The farm was a boarding, clinic and showing farm that housed a diverse group of breeds and disciplines. Skylar grew up riding and competing in English, specializing in hunters. She participated in pony club, fox hunts, and regional level horse shows. In 2011 Evans qualified for the ASPCA Maclay horse trials. She felt fortunate because she was exposed to so many breeds of horses and disciplines of riding. In high school she began teaching riding lessons under Tom Newton and fell in love with helping people create connections with horses. Amidst her hunter accolades she also has a solid foundation in western riding including western pleasure, gaited and barrel racing.

In 2017, Skylar became an instructor, horse trainer, and clinician for Parkerman Stables in Fayetteville, Arkansas where she taught hunters, western and developed their show team. After returning to Virginia in 2018, Skylar rode racehorses for a time for Woodberry Paine. In 2019-2020, she went on to be the Assistant Manager at Hearthstone Farm in Keswick, Virginia. There she had the opportunity to work closely with Sue Grossman, Zack Parks, Glenn Moody, Jimmie Lee, Kenny Wheeler, and Richard Taylor to name a few. 

"I believe that foundation comes first with any horse and rider regardless of age or level. I also firmly believe in working with the horse not against the horse and building that team aspect with your horse. I believe in focusing on the little things. You cannot rush perfection, and because of that I build the whole mental and physical foundation with both horse and rider before advancing. I feel what sets me apart from other instructors is my patience, developing softness in the horse and always having my mind open to more knowledge. I grew up in the whole world of horses and because of that I know what it takes to achieve greatness in the saddle."

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