December of 1957 saw the grand opening of the Old Town School of Folk Music at its first home on 333 North Avenue, in Chicago. The first five years of the School's history mirrored the boom in folk music at that time. Enrollment grew and programs expanded. Over 150 students attended guitar and banjo classes on a weekly basis. Folk dancing, and family sing-alongs rounded out the programming.
The late 70s marked a decline in enrollment, concert attendance, and the beginning of a severe financial crisis that left the School on the brink of bankruptcy. In 1982, the School's staff and Board expanded the scope of programming to include ethnic and traditional music from around the world. This lead to a successful rebound from tragedy, allowing for the expansion opportunities that followed in the 1990's.