Engagement in youth development programs reflects the quality of young people's program-related experiences. However, more research is needed that explores cognitive, emotional, and behavioral dimensions of engagement in programs that serve underrepresented youth of color. The present crosssectional and mixed-methods study assessed potential relations among dimensions of engagement in the Boston-area Scoutreach initiative, character attributes, self-perceived school competence, and intentional self-regulation. We analyzed data from 32 Scouts (M age = 9.97 years, SD = 2.46, Range = 6 to 14), 32 parents/guardians, and five Scoutreach leaders. Scouts demonstrated that they were cognitively, emotionally, and behaviorally engaged in Scoutreach, and these dimensions were related differentially to indicators of healthy development. Qualitative data elucidated key aspects of Scoutreach (e.g., camping, peer relationships) that were linked to youth engagement. We discuss limitations of the present study and implications for future research and practice.