As his family was disintegrating around him, Parsons developed strong musical interests, particularly after seeing Elvis Presley perform in concert on February 22, 1956, in Waycross. Five years later, barely in his teens, he played in rock and roll cover bands such as the Pacers and the Legends, headlining in clubs owned by his stepfather in the Winter Haven/Polk County area. By the age of 16, he graduated to folk music, and in 1963 he teamed up with his first professional outfit, the Shilohs, in Greenville, South Carolina. Heavily influenced by The Kingston Trio and The Journeymen, the band played hootenannies, coffee houses and high school auditoriums; as Parsons was still enrolled in prep school, he only performed with the group in select engagements. Forays into New York City (where Parsons briefly lived with a female folk singer in a loft on Houston Street) included a performance at Florida's exhibition in the 1964 New York World's Fair and regular appearances at the Café Rafio on Bleecker Street in Greenwich Village in the summer of 1964. Although John Phillips (an acquaintance of Shiloh George Wrigley) arranged an exploratory meeting with Albert Grossman, the impresario balked at booking the group for a Christmas engagement at The Bitter End when he discovered that the Shilohs were still high school students. Following a recording session at the radio station of Bob Jones University, the group reached a creative impasse amid the emergence of folk rock and dissolved in the spring of 1965.