This article examines the relevance of humor to student engagement in outdoor education. A sociocultural framework is applied to this examination, based on a view of learning as constructed, cognitive, embodied, and affective. A set of affordances of outdoor education as a contextually situated learning activity is identified along with related abilities of adolescent students to interact with these characteristics. The argument, advanced through an examination of the literature, is that outdoor education provides teaching and learning affordances that are different from traditional school-based education, and the ability of students to engage with these affordances is influenced by a range of affective factors. Furthermore, humor acts as an influential variable in learning environments, thus providing a trigger for increasing students' emotional engagement with the immediate task or topic. The primary proposition is that a capacity to knowingly perceive and productively engage with humorous moments can provide a pedagogical trigger for the emotional engagement of participants. In particular, we outline how humor is likely to influence student-student, student-teacher, and individual-context learning-related interactions.