Music is central in the lives of adolescents. While listening is usually the most common form of engagement, many adolescents also learn music formally by participating in school-based and extracurricular programs. This study examined positive youth development (PYD), school connectedness (SC), and hopeful future expectations (HFE) in middle school students (N= 120) with four levels of musical participation in school-based and extracurricular music programs. Levels of participation were based on students’ engagement in different music programs, including the Virtual Middle School Music Enrichment (VMSME), a tuition-free, extracurricular program that focuses on popular music education and virtual learning. We also investigated student listening preferences, musical tuition, and daily instrumental practicing.