While college is perceived as a given for many middle- and upper-income students graduating from high school, the transition from secondary to higher education is a much more complicated one for low-income students, particularly poor and working-class students of color. This article focuses on the critical juncture--one that is under-explored in both the literature on secondary schools and higher education--that these students arrive at when they graduate from high school, and their decision-making processes about whether or not to attend college. What are students worried about? Who are they receiving help from? What do they already know and not know about colleges and the differences between them? How are they making choices about where to apply, and then where to go? What stumbling blocks do they encounter, what are their doubts and fears? Drawing on research conducted at three small urban public schools over the course of a year, this article offers an important lens on the ways that social class shapes students' developmental experiences and choices, paving some roads and obstructing easy access down others.