Oakland Plantation was founded on a 1785 Spanish-era land grant by Jean Pierre Emanuel Prud'homme, and a small enslaved work force first grew tobacco and indigo there. The skills and strengths of enslaved Africans, from domestic and agricultural labor to crafts such as blacksmithing, carpentry, and masonry, were vital to the plantation's survival. After the cotton gin was invented in 1793, Emanuel Prud'homme purchased a mechanical gin, and cotton became the plantation's main crop as textile mills increased demand and the use of enslaved labor grew. By the Civil War, nearly 150 enslaved people labored there. After the Civil War and into the 20th century, life continued to revolve around cotton as descendants of enslaved workers remained as tenant farmers and sharecroppers and new families moved there for work. The legacy of families including Helaire, Metoyer, Williams, Toussaint, Shields, and others remains, with many descendants still living nearby. The plantation survived the Civil War, Reconstruction, boll weevils, and the Great Depression, but increasing mechanization, beginning in the 1930s and accelerating after World War II, brought the plantation era to an end. The last tenant family left in the early 1960s. The main house, built in 1821 and updated over time, remained the Prud'homme family home until the National Park Service acquired it in 1998. For nearly two centuries, generations of owners and workers, enslaved and tenant, lived and worked there and kept the plantation in operation.