[2] Born and raised on a farm in Riderwood, Maryland, United States,[1] Clifton's family prospered in the tobacco trade during the nineteenth century.

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.

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.

[3][4] Clifton met banjo player Johnny Clark through Sadler and soon formed a band that began playing on many local radio stations (including WWVA).

His songbook included many songs such as "Little Maggie", "I'll Be All Smiles Tonight", "Long Journey Home", and "Little Whitewashed Chimney".

The festival featured many of the biggest acts of the day in bluegrass music including Bill Monroe, the Stanley Brothers, Jim & Jesse, Red Allen, Frank Wakefield & The Kentuckians, Mac Wiseman and the Country Gentlemen.

[4] In 1963, Clifton's family moved to England and he toured all over Europe playing in local folk clubs.

In the 1970s, he signed with County Records and formed the First Generation band, consisting of Clifton on guitar, Red Rector on mandolin and Don Stover on banjo.