In 1921 Wilson moved to Martinsburg, West Virginia, to join the Martinsburg Mountaineers of the Class "D" Blue Ridge League. After breaking his leg while sliding into home plate during his first professional game, he was moved from the catcher's position to the outfield. In 1922 he met Virginia Riddleburger, a 34-year-old office clerk; they married the following year. In 1923, playing for the "B" division Portsmouth Truckers, he led the Virginia League in hitting with a .388 batting average. Late in the season, New York Giants manager John McGraw purchased his contract from Portsmouth for $10,500.