Between 2004 and 2005, Maitland was a member of the progressive rock supergroupKino. Throughout his career, Maitland has been involved with many West Endmusicals, and from 2005 onwards, he has been playing drums on the Mamma Mia! International Tour. His musical activity seems to have waned a little bit in the last couple of years. Aside from these links listing professional drumming engagements, having trained at the Mackenzie School of Speech & Drama and taken LAMDA examinations regularly since the age of eight, between 1985 and 1993 Chris became involved in theatre at Cambridge as an actor. Also during this period he built up a practice of private percussion pupils and from 1989 took on various posts as a professional drum-kit teacher. As an actor, he has played a wide variety of roles, including Shakespearean.
On the 17th April 2011 in Zoetermeer, The Netherlands, Maitland was supposed to reunite on stage with Porcupine Tree's bass player Colin Edwin and no-man's singer Tim Bowness as part of the Memories Of Machines project (a collaboration between Bowness and Giancarlo Erra of Nosound). However, the concert was eventually called off.