Rosemont Plantation is the ancestral home of the Cunningham family beginning in 1769, when Patrick Cunningham moved from Virginia to Laurens County and what would become known as Rosemont plantation. The Cunningham (formerly Cuningham) family was originally from Scotland. His brother, Robert, also moved from Virginia to the 96 District, where the two received land grants. At this time, the head of a family could apply for a land grant of 100 acres plus 50 acres for each dependent. Dependents could include family members, servants, and slaves. Both brothers fought on the side of the British during the Revolutionary War. When the fighting ended, Patrick was permitted to return to South Carolina, paying 12% of his holdings to satisfy requirements of the Confiscation Acts. Robert's petition to return to South Carolina, however, was denied. He lived out his remaining years in the Bahamas.

Prior to the Revolutionary War, Patrick received multiple land grants totaling 600 acres. Records indicate that Cunningham then purchased around 1400 additional acres during his lifetime. At the time of his death, Cunningham owned 46 slaves. This would have been sufficient for working a portion of his land, but likely much remained wooded and in its natural state. 

Upon Patrick Cunningham’s 1796 death, his property, including the plantation and enslaved workers, was left to his wife Ann and his three sons, John, William, and Robert. His son Robert controlled the plantation in the 1840s, at its peak, during which time it included several thousand acres. Based on census records and an inventory of the plantation at the time of Robert Cunningham’s 1859 death, the number of enslaved workers on the plantation ranged from 101 in 1830 to 155 in 1859, with his wife, Louisa, reported to own around 140 enslaved persons in 1960. The plantation's main crops were indigo, cotton, and tobacco.

Louisa Cunningham was a lover of plants and flowers, and an avid gardener. This may have led to the name of Rosemont for the plantation, whose grounds included 7 acres of gardens at the time. These gardens, however, could not be kept up following the Civil War. Ann Pamela Cunningham was born to Robert and Louisa Cunningham in 1816. Ann Pamela Cunningham would live at and manage the plantation during the Civil War, despite being bedridden following a horseback riding injury in her late teens.

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