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.
Throughout the decade, Wakefield also performed with Jimmy Martin and the Sunny Mountain Boys, as well as Marvin Cobb and the Chain Mountain Boys. He recorded his first 45 RPM, which included his most famous bluegrass song, "New Camptown Races," in 1958. In 1958, Wakefield rejoined Red Allen and his band the Kentuckians.