12. Challedon (1936-1958)

He won the 1939 Preakness in a quagmire -- the first Maryland-owned horse in 62 years to capture the second leg of the Triple Crown. Bred and trained at Glade Valley Farm, Challedon won 20 of 49 lifetime starts. The bay colt also finished second in the Kentucky Derby to Johnstown, another Maryland thoroughbred whom Challedon then upset at Pimlico. Twice U.S. Horse of the Year, Challedon thrived at local tracks, winning both the Maryland and Pimlico Futurity as a two-year-old, and twice taking the Pimlico Special. At four, he won five of seven starts, including the 1940 Hollywood Gold Cup in which Challedon, ridden by George Woolf (Seabiscuit's jockey), set a track record. Today, a golf course in Mount Airy bears Challedon's name.
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