The purpose of this study is to examine the impact attending an extended outdoor orientation program has on first-year students at a mid-size public institution in the Southern US. The study sought to strengthen and contribute to existing research by comparing the experience of students who just completed their first year of college within an institution utilizing a measure of sense of belonging in addition to other indicators such as retention and academic success. The researcher requested participation in a survey of all students who entered as new students during summer 2018, creating a study group of students that attended outdoor orientation, and a comparison group of students who did not attend. Academic success was measured quantitatively through comparing the following data across both groups (students who participated in an outdoor orientation program versus those who did not): 1) Self-reported and institutional data on GPA, 2) Self-reported information including approximate hours spent studying during the academic semester and missed classes. Belonging was measured quantitatively through an instrument based on Hoffman et al. Sense of Belonging Scale (2002). Student retention data was provided by the Office of Institutional Research during the Fall of sophomore year based on enrollment status. Open-ended responses were also utilized to create a narrative of the student experience of attending outdoor orientation. Statistical analysis and data disaggregation found no statistically significant difference between groups across sense of belonging or academic success indicators, but showed an increase in retention of students who did attend the outdoor orientation program. Student feedback provided a useful narrative to further contextualize and understand their perceived impact of attending outdoor orientation. Implications for future research and student affairs practitioners working directly with orientation and first year transition programs are discussed in light of the findings from the statistical analysis.