Postsecondary educational attainment is an important determinant of future economic opportunity and social mobility. However, sizable gaps in educational attainment exist within communities and across sociodemographic lines. The goal of this research is to develop processes and methodologies that could be applied across a variety of geographic areas to better understand why postsecondary attainment varies across communities. Academic persistence is influenced by factors that go beyond the individual student, to include contextual and institutional influences. We developed a study of 21 high schools within two distinct geographic regions of Virginia: Richmond City and surrounding rural counties and the Roanoke and Appalachian region. We used nearly 70 publicly available administrative, survey, and opportunity datasets from across multiple organizations to characterize the high schools, the student body, and the communities. These data informed predictive models and statistical analysis for exploring factors that influence student outcomes after high school. We found that influencing factors varied by student characteristics (e.g., economically disadvantaged) and high school location (urban versus rural). We must account for the unique characteristics of the student and the communities to develop targeted strategies that encourage postsecondary enrollment.