As a young man, Hamilton met and played with Woody Guthrie at Will Geer's artist colony in Topanga, California in the mid-1950s. In 1956 Frank Hamilton met Win Stracke and Dawn Greening (who started the Old Town School of Folk Music in her kitchen in Oak Park) at the Gate of Horn. Using teaching methods he observed with Bess Lomax in Topanga Canyon, together, Win, Dawn and Frank founded the Old Town School Of Folk Music in Chicago. There they developed a teaching method with an emphasis on group learning. On the opening night, Frank taught the class a song demonstrated by Big Bill Broonzy. Frank served as dean of the school also teaching guitar and banjo. Among his students was Jim McGuinn, later known as Roger McGuinn, a founder of the BYRDS. He taught Jim to play the 12-string guitar and the banjo. Frank left teaching when he joined The Weavers, with whom he played from 1962-1963.