Whether and where students begin college after high school profoundly affects their degree completion and ultimate educational attainment. Students' college access is influenced not only by individual characteristics, but also by economic, social, and schooling contexts. Accordingly, using data from the Educational Longitudinal Study, 2002 (ELS:2002), we conducted three-level hierarchical generalized linear modeling (HGLM) to explore how student and family, high school, and state contextual characteristics are associated with high school graduates' college enrollment in 2-or 4-year higher education institutions. We paid particular attention to the unique role of race/ethnicity in college enrollment, along with other demographic and academic, social, and cultural capital factors. Findings indicate significant challenges in college access for Latino students, and for students from low-income and first-generation backgrounds. Habitus and different forms of capital, and elements of high school's college-going culture also appear to be critical in college enrollment. This study affirms that a high school student's enrollment trajectories should be understood from a holistic perspective that considers how individual students' college enrollment is affected by the high school they attended and the state where they lived. Implications for future research, policy, and practice, particularly those that relate to recruiting a racial/ethnic and socioeconomically diverse college-student population, are discussed.