In the fall of 1862 Ulysses S. Grant and the Union Army set their sights on Vicksburg. Grant formulated a plan to march his thirty-one men from Grand Junction, Tennessee, south into the interior of Mississippi and approach Vicksburg from the rear. He would supply his army by repairing the Mississippi Central Railroad. He ordered his trusted subordinate, Maj. Gen. William Tecumseh Sherman, to advance simultaneously from Memphis with a column of infantry and rendezvous at Oxford.
The Union Army advanced into Mississippi during the first week of November 1862. Lt. Gen. John C. Pemberton’s twenty-four thousand Confederate forces, positioned near Holly Springs, quickly fell back behind the Tallahatchie River. Pemberton considered giving battle at this new position. However, a strong Union contingent under Gen. Alvin Hovey landed near Greenville and advanced inland to threaten the Confederate railroad supply line near Grenada in Pemberton’s rear. Although Hovey never seriously damaged the railroad, the movement caused Pemberton to move his forces farther south. By the first week of December, Confederate forces had retreated to the Yalobusha River.
During this period, political intrigue began to surface in the Union high command. One of Grant’s subordinates, Maj. Gen. John A. McClernand, used his political clout to obtain permission to organize an independent army to capture Vicksburg. In the fall of 1862, McClernand recruited and organized new regiments and forwarded them to Memphis. By early December, the majority of McClernand’s command had arrived in Memphis, while the ambitious general remained in Illinois eagerly awaiting orders to proceed downriver.
Grant decided to break the stalemate. He ordered Sherman to return to Memphis to take command of the forces assembled there, embark downriver, and capture Vicksburg. In essence, Grant ordered Sherman to take McClernand’s army. Throughout Sherman’s movement, Grant’s army would maintain pressure on Pemberton’s forces. On 20 December Sherman’s forces departed from Memphis.
Pemberton ordered a counteroffensive. He ordered Gen. Earl Van Dorn to capture the main Union supply depot at Holly Springs. With three brigades numbering roughly thirty-five hundred cavalrymen, Van Dorn’s column departed from Grenada on 16 December. Van Dorn’s men moved east toward Houston, Mississippi, and arrived at the town around noon on 17 December. Turning his men north, he reached Pontotoc the next day. To deceive the Federals, the Confederate column continued north through New Albany before turning west off the Ripley Road toward Holly Springs. By the evening of 19 December, his column rested between twelve and fifteen miles from Holly Springs.
On 20 December, Union troops were billeted in three major concentrations in Holly Springs. Union infantry occupied the courthouse area and railroad depot in town, while six companies of Union cavalrymen lay encamped near the city limits. The three concentrations were not in ready supporting distance of each other. Col. Robert Murphy, the Union commander at Holly Springs, failed to heed warnings from Grant about enemy activity and, as a result, his five hundred men lay in camp as dawn approached.
A Confederate officer later recalled Van Dorn’s plan of attack: “The first or head of the column was to dash into and capture the infantry camped in front of us; the second, following immediately after the first, was to sweep by the encampment, move straight into the town until it reached the street leading north to the fair grounds, then wheel to the right and charge the cavalry camp; the third . . . was to dash through the town, disregarding everything until it struck the infantry occupying the public square.” The attack ended in a complete success. Confederate cavalrymen rode roughshod over the infantry camp. The second column sent toward the Union cavalry camp found the soldiers in line for morning inspection. Although startled, the Union cavalrymen managed to mount a brief defense before being overwhelmed and forced to surrender.
The fight had ended by eight o’clock in the morning. Van Dorn’s men captured supplies worth $1.5 million, according to estimates by the Confederate commander. Rebels quickly broke open food stores and supplied themselves with new arms. Van Dorn consigned all the remaining stores to fire, and by day’s end the Union supply depot lay in ashes.
In the aftermath, Van Dorn’s command rode into West Tennessee before returning to Pemberton’s army and receiving a hero’s welcome. After the destruction of his main supply base, Grant retreated to Tennessee. Sherman landed north of Vicksburg at Chickasaw Bayou and suffered a bloody repulse. Grant’s first attempt to capture Vicksburg had ended in failure.
- Edwin C. Bearss, The Vicksburg Campaign, vol. 1, Vicksburg Is the Key (1985)
- Arthur B. Carter, The Tarnished Cavalier: Major General Earl Van Dorn, C.S.A. (1999)
- Robert G. Hartje, Van Dorn: The Life and Times of a Confederate General (1967)