Learners thrive when they have the capacity to regulate interest and goal direction. Through direct experiences that are interesting and goal-relevant, learners can internalize and better understand their own agency in the learning process. This article further examines this premise in an outdoor adventure education (OAE) context through two interrelated studies. The aim of the first study was to investigate the potential of OAE to afford more frequent experiences that are interesting and goal-relevant. The aim of the second study was to build on the findings from the first study and determine if exposure to OAE programs might lead to more self-directed learning. The results partially support the premise that OAE can foster experiential self-regulation.