Outdoor orientation programs (OOPs) use wilderness or adventure experiences as a transition of incoming first-year students to college and university settings. We explored resilience and flourishing outcomes from two OOP trips in Virginia and North Carolina using the Brief Resilience Scale, the Mental Health Continuum Short Form, and a thematic analysis of participant responses to open-ended survey items. Results illustrate a statistically significant, large effect size difference in flourishing between pre- and post-trip responses (d = 0.89), and the thematic analysis of open-ended post-trip questionnaire items illustrated the attainment of each of the program's OOP objectives. These results mirror previous findings evidencing the continued importance of this form of experiential learning to engender student success in higher education settings and further justify OOPs' inclusion within a high-impact practices framework.