This chapter explores the roles played by family, church, and community in the Black Underground Railroad movement. By mapping Black settlements, it clarifies and exposes the relationship between African American churches, settlements, and historic Underground Railroad routes. It shows how Black families sustained an important family organizational structure that drove the Underground Railroad. It explains how African American communities connected through family relations and intermarriage, church organizations, benevolent societies, and the fraternal structure of the Prince Hall Masons. It considers how maintaining family connections motivated escape from slavery, particularly when imminent sale threatened to break up the family. Finally, it highlights the ways that Black churches and their ministers helped free Blacks, or self-liberated men and women, to succeed in winning freedom for themselves and their loved ones.