Eva Cassidy was the third of four children born to Hugh and Barbara Cassidy. From an early age, she displayed artistic and musical talent. When she was nine years old, her father taught her to play the guitar, and she began to play and sing at family gatherings.
While a student at Bowie High School, she sang with a local band called Stonehenge, and received considerable praise.
At the age of eighteen, Cassidy began her professional career, singing and playing guitar in a Washington, D.C., area band, called Easy Street. This band performed in a variety of styles, at weddings, corporate parties, and pubs.
During the summer of 1983, Cassidy sang and played guitar, six days per week, at Wild World, in Maryland