The Great Dismal Swamp, located on the border between Virginia and North Carolina, covered about two thousand square miles during its antebellum era. However, extensive canal draining efforts in the twentieth century reduced its size significantly. The swamp was named after its "dismal" characteristics, which included hot and humid temperatures, dense vegetation, dangerous animals, and insects, making it an unsuitable location for human settlement. Despite this, thousands of maroons found refuge in this impenetrable and dangerous landscape.

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The borderlands of the swamp were filled with industrial activity that provided many opportunities for maroons to escape. Maroons took advantage of the massive transportation projects that cleared tens of thousands of acres of swampland for major road, canal, and railroad projects. These extensive projects required a considerable amount of manpower, attracting a steady flow of local, free, and enslaved African Americans and white workers. Maroons likely worked alongside this interracial workforce as they cut down trees, prepared wood for shipment, and built major roads and waterways. While there is no direct evidence of maroon activity in the swamp, other traces of their existence can be found in archeological digs, firsthand accounts, and their glaring absence in employment books.

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Deep inside the swamp, maroon communities thrived in isolation for generations. These communities grew crops, gathered food, hunted, raised animals, and traded with others in the borderlands to survive. For the most part, they avoided almost all contact with the outside world by relying on available resources nearby and even recycling existing tools. These communities exemplify maroon resilience to slavery, as they accepted the risks and recognized the difficult work involved in preserving their freedom.