This study extends W.E.B. Du Bois’s theory of abolition democracy by exploring the political thought of Black women in and around the city of Philadelphia, Pennsylvania between 1850 and 1880. As the historical site of the nation’s founding, the U.S. abolitionist movement, and the largest concentration of Blacks in the United States at the end of the 19th century, Philadelphia is central to the American democratic imaginary, yet Black women’s contributions to the city, the nation, and that imaginary, even by those exploring black political thought, remain largely unexplored. By returning to how Sarah Mapps Douglass, Harriet Jacobs, Harriet Tubman, Frances Ellen Watkins Harper, Fanny Jackson Coppin, and Gertrude Bustill Mossell negotiated and transgressed the newly drawn boundaries of the expanding city, the “splendid failure of Reconstruction” that Du Bois documented in Black Reconstruction takes on gendered and urban dimensions. Attending to these Black women as they adapted to global trends of enclosure, industrialization, and urbanization, I find that the political concept of fugitivity that spurned the democratic movement for the abolition of slavery retains theoretical significance beyond the antebellum period. Having a history in Black political thought, fugitivity is a paradigm through which people in their everyday practices escape the capitalist impulse to confine, detain, and commodify their existence as both capital and labor. Black women as political thinkers complicate the spatialized reality and romantic idea of “home” that underpinned both the hunting and freeing of fugitives in the years leading up to the U.S. Civil War. Their work raises the following question: what does democracy mean when the nation is built from and by those deemed “homeless”?