Through the rest of the decade Wakefield also toured with Jimmy Martin and the Sunny Mountain Boys as well as Marvin Cobb and the Chain Mountain Boys, with whom he recorded his first 45 RPM—which included his now most famous bluegrass composition, "New Camptown Races". In 1958 Wakefield reunited with Red Allen and his band the Kentuckians.
Wakefield performed with Jimmy Martin and the Sunny Mountain Boys, Marvin Cobb and the Chain Mountain Boys throughout the decade. He recorded his first 45 RPM in 1958, which included "New Camptown Races," a bluegrass song he was famous for. In 1958, Wakefield reunited with Red Allen and his band the Kentuckians.