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As environmental concerns grow, obesity rates rise, and people become further distanced from nature, some activists and public health advocates are encouraging the use of more physical modes of transportation over driving. The limited literature on commuters’ transit decisions mainly focuses on adults living in urbanized environments while paying scant attention to driving-aged teenagers, despite the importance of their daily commutes to school. Because this group is at a pivotal point in the transition to adulthood, it is likely that their decisions and behavior at this stage of life will have long-term implications for their routines concerning exercise, diet, health, transportation, and regard for the environment. Using quantitative and qualitative data from questionnaires, focus groups, and public sources, as well as Levels of Traffic Stress mapping models, this study examines the factors that shape high school students’ methods of transportation to and from school. The researcher found that infrastructure and perceptions of safety are highly associated with high school students’ mode use, while environmental concern and self-esteem are not. The article concludes with other possible motivators of mode usage and ideas for future research.