By the time of the Civil War, the Natchez Trace had lost its significance as a national road. One of the sections ran from Port Gibson toward Jackson but the route veered from the original Trace to reach Raymond. In the spring of 1863, General U.S. Grant marched his Union Army over this route after crossing the Mississippi and taking Port Gibson. On May 12, Grant's forces drew fire from a Confederate brigade, commanded by Brigadier General John Gregg, located on the southern edge of Raymond three miles east of here. After a day of bitter fighting, the Confederates retreated toward Jackson leaving their wounded in the county courthouse. This set-to convinced Grant of the need to take Jackson in order to assure the success of his forthcoming siege of Vicksburg.
