Outdoor adventure education (OAE) research has long aimed to explain and understand the inner workings of its programs. However, many questions remain, and the search for sharper methodological tools with which to deepen our understanding of OAE continues. This article is a collaborative autoethnographic investigation of the unpredictable and difficult to measure nature of wilderness educational expeditions (WEEs). It is a reflexive journey of storytelling and critical analysis that demonstrates the power of story-based research as method. The findings indicate that conventional approaches to WEE research are limited in their capacity to fully understand and explain the inner workings of WEEs. We argue that practitioners need to "trust the journey" to elicit learning that comes from responding to encounters with people and place. Furthermore, we suggest that quests for a sequenced "journey recipe" are unrealistic and do not honor the philosophical and pedagogical foundations of OAE. Finally, a case is made for alternative, rigorous research approaches to be embraced to gain richer and more nuanced understandings of the wonderfully diverse experiences that make up WEEs.