Our research evaluates the effectiveness of a community musical learning exchange (MLE) that included group singing, guided conversations, and reflection. The respondents (N = 290) who participated in the MLE included members of the Soweto Gospel Choir (n = 17), Soweto Gospel Choir Crew (n = 3), prison choir incarcerated singers (n = 41), prison choir non-incarcerated singers (n = 41), and community guest-participants (n = 188). We studied: To what extent did respondents engage in singing and conversations during the learning exchange? To what degree did the respondents perceive the various components of the learning exchange helped them reflect upon the theme? What similarities and differences existed among various groups regarding these perceptions? Results suggest the MLE model was effective for intercultural sharing and most respondents engaged in singing and conversations. The guided conversations within a musical event were novel experiences, with the majority describing these as very effective components of the MLE. Respondents noted that both these guided conversations and spoken reflections prior to song selections from prison choir members and singing together most effectively helped them engage with the theme. We offer suggestions for musical leaders to implement MLEs and we make recommendations for future related research.