His education spans private schools from New England to Florida. Eventually, he enrolled at the University of Virginia in 1949 where his love for country music expanded to folk music through fellow students, Paul Clayton and Dave Sadler. While still in college, Clifton, Clayton, and Sadler formed the Dixie Mountain Boys together and began playing professionally at small radio stations in central Virginia. Because his family was opposed to his musical activities, he took the stage name "Bill Clifton". With the help of his friends and bandmates, Clifton produced his first recording in 1952 that included an array of old-time, bluegrass, and folk revival repertoire. Clifton met banjo player Johnny Clark through Sadler and soon formed a band that began playing on many local radio stations (including WWVA). In 1953, the band signed with Blue Ridge Records and began playing traditional bluegrass. They soon appeared on the Wheeling Jamboree radio barn dance show on AM station WWVA. Clifton published a songbook in 1955 called 150 Old Time Folk and Gospel Songs, which soon became one of the most influential songbooks of its time. His songbook included many songs such as "Little Maggie", "I'll Be All Smiles Tonight", "Long Journey Home", and "Little Whitewashed Chimney". Because of the popularity of Clifton's songbook, these songs quickly became recognizable standards in the bluegrass world. During this time, Clifton met and played music with artists such as A.P. Carter, The Stanley Brothers, and Woodie Guthrie, to name just a few. He had many connections throughout old-time, bluegrass, country, and folk music - which reflected his unique repertoire and sound. His singing style was deemed to have more of a folk revivalist influence rather than a "hillbilly" sound - which was the popular sound of the previous years. Because the instrumental style of his band had more of a "contemporary bluegrass" sound along with his "folk revivalist" vocals, he was deemed one of the first "city-billies" in bluegrass music.