Littlestown played a vital part in the Civil War and during the Battle of Gettysburg. A band of Confederates entered Littlestown on the morning of June 26, 1863, the advance of Early’s Division, Ewell’s Corps, the Army of the Northern Virginia, which was crossing the Maryland line into Pennsylvania. On June 29th , General Kilpatrick’s Division of Union Cavalry camped for the night around Littlestown. Kilpatrick and General George Custer, of the Little Big Horn fame, lodged at the Barker House. The next morning, the division of five thousand men took part in a cavalry engagement with six hundred Confederates under General Jeb Stuart at Hanover.
General Pleasanton, commanding the Cavalry Corps of the Army of the Potomac, headquartered at the Barker House, where he received the word of Stuart’s defeat at Hanover. Slocum’s Corps of thirteen thousand infantry entered into Littlestown during the evening and were dispatched to Gettysburg the next day. General Sedgewick’s Sixth Army Corps of fifteen thousand also passed through Littlestown on their way to the Battle of Gettysburg.
After the battle, hundreds of wounded soldiers were brought in ambulances from Gettysburg and placed on the railroad cars at Littlestown. General Daniel E. Sickles, who had lost a leg at Round Top during the Battle of Gettysburg, was among the wounded treated in Littlestown. The land around the town was used as camping grounds by the soldiers and many fences were burned, crops destroyed, livestock confiscated, and fields damaged.