The Outdoor Pursuit Center at Miami University, Ohio, has provided an outdoor orientation experience for incoming first-year students since 1995. The experience provides an environment that is effective in easing the transition into higher education settings. Student trip coordinators, student facilitators, faculty, and professional staff use situational leadership models to develop an atmosphere that addresses anxieties, excitement, and a sense of belonging. Student challenges include environmental physical situations, mental problem solving, group dynamics, and cognitive skill utilization. A supportive environment is provided through staff efforts, daily event processing, shared responsibilities, and safety precautions. The framework of the program consists of situating the learning experience, validating student concerns, and mutually constructing meaning. Pre- and post-activity debriefings, coupled with daily reviews and processing initiatives, thoroughly investigate student feelings and apprehensions about participating in adventure activities and help to transfer participant outcomes and insights to academic life. The most effective tools in the program for summative, qualitative, and quantitative evaluations of the transition experience are group journals and focus groups. Lessons learned in formulating and implementing the program relate to developing collaborative goals, designating responsibility, determining resources, determining type of trip, and communicating with students. (SAS)