Focusing on a cohort of high school students from a Midwest metropolitan region, this study combines multiple sources of data and uses a multinomial logistic regression to model student postsecondary choices with respect to whether and where to attend college. Specifically, we examined the enrollment patterns by proximity to the home region and factors associated with these college decisions. The results suggest that these students' college choices were a process influenced by both precollege individual characteristics and social contexts. The findings also supported our hypothesis that acquisition of various types of capital and academic success of the school district (as one of several indicators of a college-going culture) were negatively related to student preferences for college proximity. These findings highlight the interplay between individual, family, community, and school at different levels as it influences college decisions of students from the deindustrialized Midwest region and regions alike.