The antebellum era is ripe with complex narratives of communal resilience and freedom. Yet, within this broader historiography, the experiences and agency of Black women have often been marginalized and overlooked. This project aims to illustrate the dynamic ways in which Black women living in ‘free’ cities of the antebellum era—namely Philadelphia, New York City, and Boston—crafted and asserted their own sense of meaningful freedom, despite, and often in direct protest of, the limitations imposed both by the law and white society. I argue that this was accomplished through their belonging to women’s philanthropic and social organizations, which utilized clothing, funerary politics, economic aid, and religion, and struggled against poverty, criminality, and perceptions of Black womanhood. My ultimate goal in this project is to offer insights which go beyond the traditional historical narratives of antebellum America and underscore the significance of daily, forgotten advocacy.