Colleges and universities have recently focused more attention on incorporating high-impact practices into their curricula, often under the auspices of the potential benefits such practices have for developmental growth and student success (Lange & Stewart, 2019). Outdoor adventure education represents an experiential practice where students can extend their learning beyond the more traditional, heavily structured classroom environment. However, due to access and inclusion barriers, students with one or more intersecting marginalized identities remain less likely to participate in these activities (Warren et al., 2014). This study investigated extreme cases of self-guided experiential learning by drawing on the experiences of three college students who took a semester's leave to backpack the entirety of the Appalachian Trail. The purposes of the exploratory study were twofold: (1) to more deeply understand developmental dynamics within self-authorship theory, particularly in how self-guided experiential learning opportunities might contribute to such development; and (2) to situate these insights by exploring what they might mean within more critical contexts.