[1] She briefly attended the Municipal College of Music, Chatham Row, Dublin—now incorporated into the Dublin Institute of Technology)—as a teenager before abandoning a potential career in opera order to sing folk and rock.
Doyle followed and they were soon to join forces with Seamus Egan and Eileen Ivers, with whom they recorded one live cassette and one track, "If I Were You" (a song penned by McKeown), which they contributed to the album Straight Outta Ireland in 1993.
In 1997, she recorded three albums: her own Bushes & Briars (Alula); Peter & Wendy, the soundtrack to the Obie Award-winning Mabou Mines theatrical production of the same name, which was composed by Johnny Cunningham; and Through the Bitter Frost & Snow, a collaboration with bassist Lindsey Horner.
Around 1992, Scots fiddler Johnny Cunningham asked McKeown to be the singer of the songs he had begun composing for the New York theatre company Mabou Mines' production of Peter & Wendy.
In the late 1990s, McKeown and Cunningham formed a duo and started an annual winter tour of music and song from the Scots and Irish traditions.
In December 2003, McKeown joined the klezmer band The Klezmatics onstage at the 92nd Street Y in Manhattan in a concert of songs they had composed to lyrics by Woody Guthrie.
In 2009, McKeown and Lorin Sklamberg, the lead singer of The Klezmatics, released Saints & Tzadiks (World Village/Harmonia Mundi), an album combining Yiddish and Irish songs.
In October 2010 she released the solo album, Singing in the Dark, an exploration of creativity and madness with lyrics from poets who lived with depression, mania and addiction, featuring musical settings of lyrics by Dalkey-born John Dowland, James Clarence Mangan, Nuala Ní Dhomhnaill, Gwendolyn Brooks, Anne Sexton, Gwyneth Lewis and others, with music composed by McKeown, Leonard Cohen, John Dowland, Violeta Parra, and Klezmatics members Lisa Gutkin and Frank London.
[3] Later in 2018, McKeown was Music Network Ireland's musician-in-residence at Dún Laoghaire LexIcon Library during which she researched the lives of extraordinary Irish women from the county whose stories were little known and composed and performed songs about them.