A Skirmish at Anderson’s Cross Roads on October 2nd 1863 was a part of Wheeler’s October 1863 Raid, fought between October 1st and 9th 1863 a Confederate raid made in southeastern Tennessee.
Following the Union defeat at the Battle of Chickamauga, Major General William S Rosecrans pulled his army back into the city of Chattanooga, Tennessee. Confederate General Braxton Bragg placed the Union troops under a siege. The Union army was forced to bring in supplies on a 60 mile wagon route from Bridgeport, Tennessee by way of Walden’s Ridge. Bragg saw a way of disrupting Rosecrans’ supplies and communications, sending his cavalry to Walden’s Ridge.
Confederate General Joseph Wheeler left on October 1st 1863 with the divisions of Brigadier General Frank Crawford Armstrong, and Major Generals William T Martin and John A Wharton. They broke through the Union screen of Brigadier General George Crook at Decatur, Tennessee and moved on toward Walden’s Ridge.
Reaching Anderson’s Cross Roads on October 2nd 1863 the Confederate Cavalry hit a train of 800, six mule team wagons, plus some sutler’s wagons. Wheeler’s men quickly captured the wagons and following orders began destroying them, killing about 1,000 mules, burning wagons and pillaging clothing and the whiskey found in the sutler’s wagon. While this was going on Union cavalry under Colonel Edward M McCook arrived. Wheeler’s pickets were driven in on both flanks by the Union troopers, but they held their position for eight hours, until after dark. The Union men recaptured many of the mules and wagons, and caused 270 casualties among Wheeler’s men.
The raid continued until October 9th 1863 when Wheeler’s men crossed the Tennessee River at Rogersville, Alabama. They had been pursued by Union troopers for over 57 miles and took heavy losses, it was said that Wheeler’s “once proud command all but wrecked."