Bailey grew up in Pittsburgh, Pennsylvania as part of a musical family. She started playing the guitar at 13. At first she was primarily interested in rock music and after a few years she heard Wes Montgomery play on the radio and discovered jazz. She attended Berklee College of Music in Boston.After college, she taught music in Baltimore and was a finalist in the Thelonious Monk Competition before moving to New York City in 1988 to further her career as a performer. She released her first album, Little Misunderstood in 1995. It featured musicians George Colligan, Vince Loving, and Chris Battistone. In 2001, Bailey released Reunion of Souls with guitarist Chris Bergson, featuring Ashley Turner and Sunny Jain.[6] Stewart Mason of Allmusic called one of the tracks "charming" and one "perfectly sweet"  This was followed by The Power of 3! in 2002 which contained eight tracks all written by Bailey. Allmusic's Rick Anderson said that each track was "a gem" and "more complex than you'd guess at first listen". Overall he said the album was "highly recommended". Her next album was 2004's Bull's Eye with the Sheryl Bailey 3. In 2006, Bailey released her fifth album with the Sheryl Bailey 3, Live @ the Fat Cat and was a headline act at the Pittsburgh Jazz Festival. Her sixth album, A New Promise, produced by Grammy winning producer, Marty Ashby for MCG Jazz was a tribute to the late Emily Remler, featuring compositions by Remler and Bailey, and arrangements by Mike Tomaro for the 3 Rivers Jazz Orchestra.  Currently she is the Assistant Chair of Guitar at Berklee College of Music, and in addition to her own projects has recorded and toured world wide with: George Garzone, Jerry Bergonzi, Anat Cohen, David Krakauer, to name a few. Her organ trio, The Sheryl Bailey 3 will be celebrating 25 years together in 2026 and releasing a follow up to their acclaimed Cellar Live release, A Meeting Of Minds later in 2026. Recent releases include "Extra Extra" from Jerry Bergonzi, "Happy Song" and "Triple Helix" with the Anat Cohen Tentet, "Homage" from her SBQ quartet, and "Taurus Power," with Mary Ann McSweeney, Jerry Bergonzi, Mike Fahn and Austin McMahon.