This article examines the impact of an outdoor orientation program (OOP) on a cohort of first-year university students who participated in a canoe trip facilitated by peer leaders. The curriculum included training for outdoor skills and transitional guidance to university life (i.e., strategies for time management, critical thinking, becoming independent, diversity, and information about interpersonal relationships and healthy living). Employing McMillan and Chavis’s (1986) community development model and a qualitative case study approach, data were collected via a structured focus group designed to investigate the impact of the OOP on students’ adjustment to university life. Results of the study revealed that the OOP experience favorably affected students through the development of a strong sense of community, the facilitation of knowledge transfer from the wilderness context to the university setting, and the generation of a definitive sense of commitment and institutional loyalty to the university.