Census data indicates people with higher levels of education are leaving Appalachian Kentucky as they do in other rural areas. Aside from anecdotal information and primarily qualitative community studies, there is little quantitative evidence of the factors which may influence these migration decisions. State policies and regional efforts to increase educational attainment of people in the region have focused on producing more college degrees however may be contributing to the out-migration of those with higher levels of education. The study incorporates community level data with demographic, academic, and employment data from a cohort of 2005-06 college graduates from Appalachian Kentucky. The study includes an analysis of migration rates for a variety of different types of graduates and a set of three complimentary logistic regression models developed to understand the impact of individual demographic and academic factors, factors about the communities where these graduates came from, and the factors related to the communities where they went after completing their degrees and credentials to predict likelihood of migrating. This study builds upon previous efforts by providing extensive, externally validated data about a large population of individuals. It leverages sociological, demographic, and neoclassical microeconomic research methods and leverages data from Kentucky's statewide longitudinal data system to serve as an illustration for how these systems can be used for complex statistical analyses.