The purpose of this multiple case study was to investigate what students in three high school music groups perceived as most meaningful about their participation. I also examined the role that context played in shaping students' perceptions, and sought potential principles underlying meaning and value in instrumental ensembles. Over the course of six months I conducted a series of in-depth, semi-structured interviews with six student wind ensemble members, five student guitar class members, and six jazz band members at three high schools in Winnipeg, Canada. I interviewed the participants' music teachers and school principals, observed rehearsals and performances, and spoke informally with parents and peers. Drawing upon praxial and place philosophies, I examined students' experiences within the context of each music group, and looked for themes across the three groups. What students perceived to be meaningful about their participation was multifaceted and related to fundamental human concerns. Students valued opportunities to achieve, to form and strengthen relationships, to construct identities as individuals and group members, to express themselves and communicate with others, and to engage with and through music. Although these dimensions were common to students in all three groups, students experienced and made sense of them differently, and thus experienced meaningful participation in multiple, variegated ways. Context played a substantial role in shaping not only the dimensions of meanings most salient to participants but also the ways that music experiences became meaningful for those involved. What students value and find meaningful about their participation in instrumental music education has been neither well documented nor thoroughly explored. This study raises questions about the ways that meaningful musical engagement might extend beyond the boundaries of school, and contributes student perspectives sorely needed in ongoing conversations concerning the relevance of music education in students' lives.