In this chapter, the potential for creative musical development of older adult novice musicians is analysed and discussed. Research concerned with music, health, and ageing has highlighted the importance of creativity as well as the wider benefits of music participation among older adults. However, little attention has been paid to the potential for later-life musical development, or to the relationship between creative experience and later-life musical development. In particular, the pedagogical orientations that could support later-life creative musical experience and development have not been explored fully. Our chapter draws upon two contrasting case studies: one based in a community centre and the other in long-term care, where older adults took part in weekly music workshops over an eight-week period. We present our observations of indicators of creativity and musical developmental processes, based on an event-sampling approach to analysis of video recordings of the music workshops. The analysis was guided by the Sounds of Intent framework for musical development, comprising its three domains of reactive, proactive, and interactive musical behaviours. Co-creativity, implicit within the Interactive domain of the Sounds of Intent framework, served as a theoretical framework for the identification of creative musical encounters. Our results revealed that co-creative musical development became more sophisticated over time in both groups, suggesting that musical development and co-creative musical experiences are possible within diverse contexts involving older adults.