This study examined student experiences participating in a peer-led three-day wilderness canoe excursion in Northern Ontario, Canada. This program is a mandatory outdoor experience program (MOEP) for third-year students and is the final course in a progressive series of outdoor experiences offered at the beginning of the first, second, and third year. Guided by principles of realist evaluation, the written reflections from consenting students in the 2015 MOEP cohort were analyzed to identify the contexts and mechanisms associated with enjoyment or lack of enjoyment of their trip. These findings will help improve the MOEP program and have implications for similar intentionally led outdoor programs offered at other higher education institutions.