Peer mentorship is an effective approach for delivering health promotion programs that may be particularly useful among underrepresented populations. Advancing the peer-led approach, the Indigenous Youth Mentorship Program (IYMP) is a communal-led program rooted in Indigenous values aimed at the promotion of healthy lifestyles in children and youth. The program includes layers of multi-age mentoring (i.e., elementary students, high school student mentors, and young adult health leaders [YAHLs]) and incorporates three core components: physical activity, healthy eating, and cultural teachings. The purpose of this study was to qualitatively explore elementary student, mentor, and YAHL experiences in an urban IYMP offering. Eleven sharing circles were conducted; six with elementary students (n = 23; grade 4 and 5 students), two with mentors (n = 3; students enrolled in a grade 10 wellness girls class), and three with YAHLs (n = 6; undergraduate university students). Focus groups were also held with respective school teachers and principals. An inductive content analysis generated three themes that represent the perceived impacts of this urban IYMP offering: (1) Fostering Wellness, (2) Strengthening Meaningful Connections, and (3) Exploring Leadership. Findings are positioned within a communal mentorship framework that is circular and multi-directional. By bringing together Indigenous and non-Indigenous peoples, this program offering supports Indigenous cultural relevance in an urban-based wellness program.