Pre-trip anxiety is a critical yet understudied factor influencing participation and engagement in Outdoor Experiential Education (OEE) programs. Anxiety can serve as both a motivator and a barrier, shaping participants' willingness to engage in challenging activities. This study examines the sources, predictors, and temporal progression of pre-trip anxiety among OEE participants, with a focus on experience level, gender differences, and activity type. Using a cross-sectional design, data were collected from students and staff at two Midwestern universities across three time points leading to an OEE program. Measures included the State-Trait Anxiety Inventory (STAI) and a course-specific worry scale assessing concerns such as physical ability, social dynamics, and environmental risks. Results indicate that experience level can predict anxiety, with less experienced participants reporting higher levels of concern. Gender differences were also observed, with female participants exhibiting greater pre-trip anxiety, particularly in water-based activities. However, anxiety remained relatively stable across time intervals, suggesting that interventions may be effective at multiple stages before a program begins. These findings have practical implications for OEE design, including targeted pre-trip interventions, adjusted program marketing, and tailored support strategies to reduce barriers to participation and enhance student preparedness.