General Earl Van Dorn, a Confederate officer famed for daring raids of both military and domestic natures, demonstrated the former in December of 1862 here in Holly Springs.
Earlier that year, Union General Ulysses S. Grant had begun moving munitions and supplies down the Mississippi Central Railroad toward Vicksburg, a key fortification on the Mississippi River. Grant’s army swept into Holly Springs, where the General set up his headquarters at the gothic antebellum mansion named Airliewood, while installing his wife and son in the town’s most lavish mansion, Walter Place. By the middle of November, he had established a supplies and munitions depot in Holly Springs before moving on to establish headquarters in Oxford, some thirty miles further south.
On December 20, 1862, Van Dorn led a cavalry force of 3,500 into Holly Springs, surprising the slumbering Federal forces there. Although few died—1,500 Union soldiers were captured and quickly paroled—the destruction of supplies was massive. Fires lit the skies and smoke clogged the air. Thousands of bales of cotton, intended for sale to finance Grant’s army, were burned; railroad car after railroad car packed with bacon was torched, great pools of fat spreading out beneath. Estimates at the time set the damages at $1 million for the loss of medical supplies alone.
Many structures in Holly Springs were lost, including the courthouse, the railroad depot, and a majority of the town square; but the humiliating loss to Grant set his Vicksburg campaign back three months and raised Van Dorn to heroic status.
Markers have been erected throughout Holly Springs describing crucial events and places where the raid took place. (You can pick up information on the Van Dorn Raid, as well as a map of the markers at the Tourism Bureau.)