Black activists Frances Ellen Watkins Harper and Harriet Tubman, during the height of their involvement in the antislavery movement, lived as unmarried women amid a mid-nineteenth-century culture that ostensibly devalued singleness. This essay examines nineteenth-century newspapers and William Still’s social history The Underground Rail Road (1872) to reveal how antislavery culture wavered in its representation of single black women. On one hand, antislavery rhetoric emphasized black marriage as the epitome of civic freedom, while on the other hand admitting that women such as Tubman and Watkins Harper could lend their time and finances to abolitionism largely because they were not married. Eluding popular stereotypes of single black women as criminals and deviants, Tubman and Watkins Harper instead etched out more favorable reputations through the rhetoric of single blessedness, which considered single women’s vocations and charity as indirectly supporting heteronormative marriage rather than challenging it. Reading through the lens of black feminist scholarship and recent research in singleness studies, this essay traces how the period of mid-life singleness for Tubman and Watkins Harper became a productive, but contested, stage of their public activism.