She grew up in Fredericksburg, Virginia, and now lives in Massachusetts. McKeown began her career in the folk scene. She released her first album, "Monday Morning Cold" in 1999 on her own label (TVP Records), travelling throughout New England while a student at Brown University in order to promote the record. Although she had begun studying ornithology, she graduated from Brown with a degree in ethnomusicology. Early in her career, she collaborated with Beth Amsel, Jess Klein, and Rose Polenzani; the four of them performed as Voices on the Verge.