Despite this image taken over a colossal spread fence at the 1941 Piping Rock Horse Show in New York, Sara Bosley Secor was a talented, well-known equestrienne and came from a family of strong Mid-Atlantic horsewomen.

Her mother, Elizabeth Cromwell Bosley, bred and trained the famous sprinter Chase Me, and her sister, Elizabeth C. “Betty” Bird became the first woman to train a Maryland Hunt Cup winner.

Growing up in rural Monkton, Md., Sara began training Chase Me when she was 12 years old, teaching him to retrieve sticks, shake hands and steal handkerchiefs from pockets. Just before his first race (which he won by 20 lengths), Chase Me plucked a cigar out of the starter’s pocket.

The brown colt went on to win every race he entered until breaking down in the spring of 1934 at Belmont Park (N.Y.). Six years later, Mrs. Bosley died in a car accident at the age of 45.

But Sara rallied through the tragedies and continued on in the horse world for decades to come, showing, training, hunting and eventually becoming master of the Elkridge-Harford Hunt Club (Md.) in 1972. She rode every day and hunted twice a week into her 60s.

“She was the confidante of practically everyone, and was never judgmental,” said longtime friend Bonsal White in her Baltimore Sun obituary. “She was the most unforgettable character I’ve ever known, in addition to being a fabulous horsewoman.”