In the Western Theater of the Civil War, Major General U.S. Grant began his thrust against Vicksburg, Mississippi, by sending dispatches from his forward headquarters in Oxford, Mississippi, to execute his plans.
Orders were dispatched from General Grant to his chief of cavalry, Colonel Theophilus Lyle Dickey of the 4th Illinois Cavalry, 13th Army Corps. These orders would begin a raid on the Mobile and Ohio Railroad.
Unknown to both, this raid not only would hinder the Confederate war effort, but also would have severe implications on Grant's strategy upon Vicksburg. Failure of communications would allow Confederate Major General Earl Van Dorn to raid Grant's critical supply depot at Holly Springs, Mississippi.
Camped a few miles east of Water Valley, Col. Dickey received his orders from General Grant on the night of December 13, about 11 p.m. His orders were to take part of his division of cavalry and destroy the Mobile and Ohio Railroad as far south as possible. At 9 a.m. on Sunday the 14th, Col. Dickey picked a small escort from Company F, 4th Illinois Cavalry. Also included were Colonel Edward Hatch's detachment of 800 men from the second Iowa Cavalry and the seventh Illinois Cavalry. Dickey then set out on his expedition traveling the road for Okolona by way of Pontotoc.
On the march to Pontotoc, the Federals encountered small scouting parties of Confederates, which Dickey's command captured. The command reached Pontotoc at 9:30 on Monday morning after a 45-mile march in a gentle rain.
Citizens informed Dickey that a body of infantry from Bragg's army was encamped nearby. One group was reported to be camped 5 miles east of Pontotoc on the road to Tupelo, and another body camped near Tupelo.
Dickey sent a small reconnoitering party dashing on the Pontotoc-Tupelo road. After splashing on the road 5 or 6 miles, the party found no enemy and returned to Pontotoc.
While at Pontotoc the gentle rain changed into a violent storm and the roads became sodden. At this time, Colonel Dickey ordered all of the ambulances and prisoners sent back under an escort of 100 troopers. Two wagonloads of leather with the Federal Government surveys and township maps of the State of Mississippi were included.
From Pontotoc, Major Datus E. Coon of the 2nd Iowa Cavalry, accompanied by 100 men armed with Colt revolving rifles, destroyed Coonewah Station, the telegraph line, railroad, and the railroad bridge north of Okolona.We are currently offering the following pieces from the Mobile & Ohio Railroad Company: