Confederate cavalry leader General J.E.B. Stuart loots Chambersburg, Pennsylvania, on a daring raid in the aftermath of the bloody Battle of Antietam in Maryland.

Stuart left Virginia on October 9 with 1,800 cavalrymen. At the time, the Union Army of the Potomac was still camped in western Maryland. Its commander, George McClellan, was reluctant to pursue General Robert E. Lee's Army of Northern Virginia back across the Potomac after Antietam on September 17.

Stuart was trying to gather information on McClellan's army and harass his supply lines. As the Rebels rode through Maryland, in an effort to keep their activities secret, they captured any male travelers they saw; Stuart refused to detain women. On the evening of October 10, the Confederate troopers entered Chambersburg. About half of the supplies for the Union army came through the rail center, and Stuart planned to destroy a railway bridge in the town. Local officials fled, and there were no Federal troops to be found when Stuart's men rode in on the evening of October 10. On the morning of October 11, they began cutting telegraph lines, seizing horses and any supplies they could carry, and destroying everything else. The railway bridge proved to be more than the Rebels could handle. Attempts to destroy the steel structure failed, and Stuart ordered his men to turn back to Virginia by the afternoon of October 11.

Stuart's men headed back through Emmitsburg, Maryland, where Stuart learned that a Federal cavalry force was waiting for him at Frederick, 20 miles south. Stuart used backroads and wove between two Union forces before crossing the Potomac River on October 12. The three-day raid covered nearly 130 miles, netted 1,200 horses, and captured 30 local officials to be exchanged for Confederate civil prisoners. Stuart also destroyed many machine shops at the rail center in Chambersburg. His force suffered just one man wounded and two missing.