Although the assumption of character development through outdoor adventure education (OAE) programs is long held, increasing scholarship questions the tenability of the supposition. Addressing this impasse, this article draws upon doctoral research I conducted into character development through OAE programs (Stonehouse, 2011) and a presentation I made on the moral worth of wilderness education (Stonehouse, 2012). I focus here on a theme that frequently surfaced throughout the investigation: the strong similarities between the structure of monastic communities, who order their time and space to nurture moral formation, and analogous structures experienced on wilderness expeditions. In likening expeditions to "traveling monasteries," I identify wilderness education as a positive locus for cultivating virtue and thus character. Although the context of this study is OAE, its aim, to identify educational environments conducive to character development, is broadly generalizable beyond the outdoors.