This study examines how and why peoples of African descent access and utilize community-based pedagogical spaces that exist outside schools. Employing a theoretical framework that fuses historical methodology and border-crossing theory, the researchers review existing scholarship and primary documents to present an historical examination of how peoples of African descent have fought for and redefined education in nonschool educative venues. These findings inform the authors' analysis of results from an oral history project they conducted into how Black Bermudian men utilized learning spaces outside schools, such as the family, Black church, and athletics clubs, to augment their personal and scholastic development. Based on their historical and empirical research findings, the authors argue that educational actors (including teachers, administrators, policy makers, and researchers) focused on school-based issues like the academic achievement gap would do well to recognize the impact learning spaces outside of schools may have on student scholastic success, particularly for minority men. (Contains 2 notes.)