Wheeler ' s October 1863 Raid Wheeler ' s October 1863 Raid ( October 1 – 9 , 1863 ) was a large cavalry raid in southeastern Tennessee during the American Civil War . Maj . Gen . Joseph Wheeler ' s Confederate cavalry scored a great initial success , but subsequently was roughed up by Union cavalry during its withdrawal south of the Tennessee River . Background . After being defeated in the Battle of Chickamauga , the Union Army of the Cumberland , commanded by Maj . Gen . William S . Rosecrans , withdrew into the city of Chattanooga , Tennessee , and was besieged by Gen . Braxton Bragg ' s Army of Tennessee . The Federals held a railhead at Bridgeport , Alabama , but because Bragg ' s army occupied Lookout Mountain , they had to bring supplies into the beleaguered city by wagon . The routes along the Tennessee River were easily harassed by the Confederates , so Rosecrans had to bring most of his supplies into Chattanooga from Bridgeport along a 60 - mile wagon route across Walden ' s Ridge . Bragg ordered Wheeler to take the bulk of his cavalry corps and disrupt Rosecrans ' s communications across Walden ' s Ridge . Anderson ' s Cross Roads . Wheeler set out on October 1 with the divisions of Brig . Gen . Frank Crawford Armstrong and Maj . Gen . William T . Martin , plus part of Maj . Gen . John A . Wharton ' s division . He quickly broke through the screen of Brig . Gen . George Crook ' s 2nd Cavalry Division near Decatur , Tennessee , and rode toward Walden ' s Ridge . On October 2 at Anderson ' s Cross Roads , Wheeler surprised a train of 800 mule - drawn wagons , plus sutler ' s wagons . The Southern horsemen easily overwhelmed the few guards and began to carry out their orders to " kill the mules and burn the wagons . " Soon , whiskey was discovered in the sutler ' s wagons and Wheeler ' s men began pillaging the wagons for new clothing and other booty . The officers were either unwilling or unable to stop what became an eight hour orgy of plundering . Soon , Col . Edward M . McCook arrived with his brigade of Union cavalry . In a series of skirmishes , McCook lost 70 men while recapturing 800 mules and a few wagons and inflicting 270 losses on the tipsy Southerners . Wharton rode to McMinnville , Tennessee , which was captured with a loss of 388 Federals and 23 Confederates . Meanwhile , Crook was able to deflect Wheeler ' s main body away from the supply base at Murfreesboro , Tennessee . Farmington . By October 7 , Brig . Gen . Robert Byington Mitchell concentrated McCook and Crook at Shelbyville , Tennessee . That day , Crook mauled Henry B . Davidson ' s brigade of Wharton near Farmington , losing 75 Federals while inflicting a loss of 310 . The pursuit continued in foul weather as some elements of Union cavalry rode as many as 57 miles . Wheeler escaped across the Tennessee River on October 9 at Rogersville , Alabama , but not before another 95 of his horsemen were overwhelmed near Pulaski , Tennessee . Aftermath . Wheeler inflicted significant damage to the Army of the Cumberland ' s supply line . He destroyed 500 wagons by Rosecrans ' s estimate and claimed killing 1 , 000 mules . However , during the pursuit , his command was badly roughed up by the Union horsemen , " his once proud command all but wrecked . " In the face of the aggressive Northern cavalry , Brig . Gen . Phillip Roddey cut short his follow up raid . Another planned cavalry raid by Maj . Gen . Stephen D . Lee was canceled after he found out that Wheeler ' s command was no longer in the field .