Outdoor programs often intentionally provide a different culture and the challenge of working out how to adapt. Failure to adapt, however, can cause symptoms of culture shock, including homesickness, negative personal behavior, and interpersonal conflict. This article links cross-cultural and outdoor programming literature and provides case examples in order to illustrate the importance of facilitating outdoor participants' cultural adaptation. Based on cross-cultural literature, successful adaptation is more likely to occur when there is adequate preparation for the new environment, understanding of the new cultural norms, and an appreciation of typical stages of cultural adaptation (i.e., honeymoon, crisis, adjustment, and resolution). These individual stages of cultural adaptation are interwoven with the typical stages of group development. By proactively using models of cross-cultural adaptation and group development, outdoor programs can better facilitate participants' cultural adjustment skills.