The old Whitesides Plantation home facing the old Aberdeen and Jacinto Public Road is located west of the Tombigbee River in Itawamba County below the old Woodlawn Post Office along Boguefala Creek. James Whitesides operated one of the larger plantations in the county. The home was built during the 1840's and was originally a two-story structure. During Reconstruction, the second floor of the home was removed to make the structure 1 1/2 stories.
James Whitesides was born during 1794 in York District, South Carolina, the son of Thomas and Isabella McTillion Whitesides. Before coming to Itawamba County during the 1840’s the family lived in Lawrence County, Alabama. James Whitesides married Sarah Guyton and their children (all born in Lawrence County, Alabama) included: Margaret (born September 22, 1822, married William P. McMasters), Thomas B. (born May 20, 1824, married Martha A. Keyes), Isabella (born March 31, 1826, married David Shumpert), Robert W. (born September 19, 1827), Catherine Edith Josephine (born December 17, 1830, married Nathaniel Ward), Major (born April 1, 1834, never married), Sarah Jane (born 1836, married Joshua W. Ward), James S. (born 1838, married Sarah E. Keyes) and Mary Ann (born March 25, 1841, married Alford R. Roberts).
James Whitesides died on December 4, 1860 on his plantation and was buried in the plantation cemetery.
During 1860, the plantation was the home to 74 slaves. An 1860 document dated December 26 of that year listed the slaves on the plantation at the time. The document enumerated the following: Amy and family, Samuel, Isom, John, Malverda, Linda and family, Ansi, Abb, Will, Elec, Adaline, Willis, Seth the younger, Emily, Lizie, Lindey the younger, Rob (Naris’s child), Jane and child, Seth, Lena, Andy, Ellen, Levi, Lamira, Visa, William, Caroline, Avizilla, Adison, Leonard, Lindsey, Hiram, Edney, Abb (Edney’s child), Clancy, Elic, Edney’s child, Shorlot, Jerry, Deanna, Jane (Shorlot’s girl), Elic (the blacksmith), Nancy, George (Elic’s boy), Elizabeth, Harriet, Lewis, Henry, George (Caroline’s boy), Sinthia, Easther, General, Mary and child, Burnel, David, Elvira, Foit, Farris, Bob, Jimberry, Donothon, Clark, White and Lucy.