Between 1845 and 1863, slaves of General Nathan Bryan Whitfield, builder of Gaineswood, constructed a drainage canal to prevent water from overflowing and flooding his plantation. Water from 2,070 acres south and east of Gaineswood had originally followed a 17 mile course to reach the Tombigbee River. The canal, approximately 1 mile long and in some places more than 30 feet deep, quickly diverts this surface water into the river at Demopolis.