A group involving Métis and Indigenous graduate students from the University of Manitoba and inner-city Indigenous youth developed and participated in an outdoor adventure-based canoe trip in Quetico Provincial Park. The five-day trip was steeped in Métis, Voyageur and Indigenous history and ceremony. This ensuing paper focuses on what is at stake when taking a decolonizing approach toward land-based education involving both Indigenous and non-Indigenous participants that aspires to (re)introduce Indigenous practices, environments and ceremonies. Inspired by recognizing the complexities involved in creating physical activity and sport programming for Indigenous youth under colonial structures within and outside of the academy, we seek to both illuminate and deconstruct the possibilities of measuring the transformative effects that such a trip has on all those involved, including the youth, mentors, and researchers. Drawing on the results of a qualitative study using both Indigenous and Western approaches, we present community-based research focusing on the impacts these experiences have on community building, identity, and decolonization.