Gaineswood was designed and built in 1843 by General Nathan Byran Whitfield, a cotton planter from North Carolina. He had moved to Marengo County, Alabama in 1834 and bought a 580-acre property from George Strother Gaines, the younger brother of Edmund P. Gaines, in 1842.
During that time, George Gaines owned the property as a US Indian Agent and is said to have met with Chief Pushmataha of the Choctaw Nation under an old oak tree on the property. There, they negotiated the terms of a treaty that would remove the Choctaw from the land and move them to a reservation. The tree became known as the Pushmataha Oak, named after the chief.
In 1843, Whitfield named the estate Marlmont, but renamed it Gaineswood in 1856 in honor of its former owner. General Whitfield sold the house to his son, Dr. Bryan Watkins Whitfield, in 1861. His daughter, Mary Foscue Whitfield, inherited the nearby Foscue-Whitfield House in 1861 upon her father's death.
The Whitfield family sold Gaineswood in 1923. In 1966, the state of Alabama purchased the residence from long-time owner Dr. J. D. McLeod. It was later turned into a house museum. It is said to be haunted by members of the Whitfield family. Evelyn Carter, the sister of General Whitfield's second wife, is one such ghost that haunts Gaineswood. She died of an unknown disease, and because she passed away in the middle of winter, she was kept in a sealed pine box beneath the cellar stairs until the ground thawed out in spring.
Apparently, this upset her spirit, as activity began shortly after this occurred. After she was buried, there were still paranormal occurrences, such as footsteps in the halls, the sound of her voice singing her favorite songs, and the feeling of her presence. She still haunts the mansion today.