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Rural students lag behind their urban and suburban counterparts in both college enrollment and completion, and parents may play a particularly important role in shaping students’ post-secondary aspirations and, if they go to college, their college transitions. This study uses boundary theory to examine how the parents of rural, first generation students matriculating at a highly selective liberal arts college understand the value of this education, influence their children’s aspirations, and experience their children’s transitions to college. Findings suggest that, despite these parents’ faith in the value of a college education, the perceived “elite” status of the college generated some fears and created unique challenges for many parents, possibly heightening the costs of rural college-going.