The developmental shifts encountered by boys during adolescence can have long-term implications for mental health. This paper describes a holistic approach to wellbeing and development (the On Queenslea Drive, or OQD, program), which draws upon a traditional Rites of Passage framework to support the development of boys during this period. This approach draws upon a boy's entire community to help him reflect and learn the skills needed to empower him to take his next steps in life. To provide a preliminary evaluation of this approach, 12 staff members involved in implementing the program in one school reflected upon their experiences and their perspectives on its impact on boys' development. Data were collected via regular journal entries and a survey. Results indicated that the program was perceived to have a positive impact in several areas, including relationships with parents, relationships with peers, and relationships and understanding of young women in the community. The program was also seen to increase independence through teaching the boys essential life skills. Boys' social and emotional vocabulary was noted also to grow while they were engaged in the program. Implications for enhancing the efficacy of the program long-term, and extending it to other context are considered.