At age 11, Cassidy began singing and playing guitar in a Washington-area band called Easy Street. This band performed in a variety of styles at weddings, corporate parties, and pubs. Due to her shyness, she struggled with performing in front of strangers. While a student at Bowie High School, she sang with a local band called Stonehenge. During the summer of 1983, Cassidy sang and played guitar six days a week at the theme park Wild World. Her younger brother Dan, a fiddler, was also a member of this working band. She enrolled in art classes at Prince George's Community College but dropped out after finding them unhelpful.