In an era of heightened educational expectations, it can be difficult to discern why would-be first-generation college-going adolescents are less likely to enroll in college than non-first generation adolescents. This article draws from cultural sociology to interpret differences in the way that adolescents socially construct the transition into college. Our data come from focus groups with 37 boys and 43 girls conducted in a racially diverse school district in central Texas in the United States. We find that adolescents are generally highly ambitious in their educational expectations. However, adolescents who would be the first in their family to attend college have distinctive cultural frames related to the postsecondary transition compared to adolescents whose parents went to college. Would-be first generation adolescents perceive going to college as being a family pioneer rather than continuing the family legacy, which represents a point of departure from their family of origin. Identifying distinct cultural frames and the ways that school context shapes students’ cultural frames enhances our understanding of social class differences in the college-going behavior of American adolescents.