Hall of Fame

Jack Calloway - Player

Inducted in 2019

Jack Calloway, a Delmar, MD native, played for his hometown Delmar Choo-Choo's as a youth, went on to star at Delmar High School, and then played with Delmar Railroaders of the Central Shore League, all in the 1950's. Widely regarded by his peers as one of the best pitchers of his era, Jack is remembered as an outstanding pitcher on several of the Delmar High School championship teams. He possessed a better than average fastball, good control, and a highly competitive spirit. Jack also pitched on the Central Shore League playoff team Delmar Railroaders in 1956 and 1957. Jack's baseball statistics and records may be hard to find, but numerous Eastern Shore Baseball Hall of Famer's attest to Jack's greatness as one of the best baseball players on the Eastern Shore in his era.