Although there is now an accepted need for initiatives that support older people's well-being, little attention has been paid to the role of those facilitating such activities. This research explored the benefits and challenges for those working in facilitating musical activities with older people. The research was undertaken at three UK case study sites, and involved 14 music facilitators who completed questionnaires and were interviewed about their work. The findings showed that there were many rewards in working with older people but also considerable challenges in terms of venues, resources, and a lack of initial and ongoing training opportunities.