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Sherry was born and raised in Rugby, North Dakota. She has always loved horses and art. Upon graduating from high school, she worked in South Carolina, breaking thoroughbred yearlings destined for the track. She even traveled with the Royal Lipizzan Stallions Show, and was also a circus aerialist and performer.

Sherry studied art at the Art Student's League in New York City. In 1992 she graduated from the Art Institute of Philadelphia with a degree in Visual Communications. She also studied at Studio Incamminati in Philadelphia.

Sherry's work has been featured on the covers of The Chronicle of the Horse, The Horse Directory, and Equine Marketer.