This essay examines representations of maroons and marronage in nineteenth-century African American literature. It argues that maroons – enslaved people who fled from bondage and self-exiled to remote places like swamps, forests, and mountains – complicate the familiar notion of the U.S. South as a place of unfreedom for African Americans during the era of slavery. Like maroons themselves, whose lives necessitated concealment, marronage has often been overlooked in nineteenth-century African American literature because it does not comport with a teleology of freedom-seeking that originates in the South and moves unidirectionally toward the supposed beacons of freedom in the North and Canada. It reveals that enslaved people who participated in acts of marronage created spaces of freedom within the slaveholding South, spaces that linked them to diasporic traditions of enslaved resistance via marronage throughout the further souths of the Caribbean and Latin America.