Born in Alabama, Art Whitehead moved with his family at an early age to Bristol where he attended Bristol Eastern, graduating in 1963. At Eastern, he participated in football, basketball and track, but basketball was his forte, as he was named all-league while playing the sport. His basketball career later included playing for the Terryville Oasis in the New England Basketball Association, where he earned all-league honors. His team won several championships.
Terryville was comprised of local standouts, as well as college players from this state and others close by. He also went beyond the NEBA and had tryouts with the Washington Bullets of the NBA and Pittsburgh Condors of the ABA. He also played for the famed Harlem Wizards. Over the years, he has coached sports at different levels, including for the Forestville Little League Dodgers, and at both Bristol Central and Bristol Eastern.