Lee's initial strategy was to descend in force on Harrisburg, and ANV generals Games Longstreet and A.P. Hill had already been ordered to march their respective corps in that direction, and had to be redirected to Cashtown.

General Henry Heth's division, of A.P. Hill's First Corps, arrived at Cashtown on June 29. Heth directed Brigadier General James Pettigrew to proceed with his brigade to Gettysburg on the morning of the 30th to secure supplies. Pettigrew discovered that federal forces were moving into the area, and returned to Cashtown.

On July 1, Heth ordered his entire division to advance to confront the Union cavalry that had dug-in on McPherson's Ridge and Willoughby Run, firing the first shots of the battle at retreating Union pickets just west of Willoughby Run on the Chambersburg Road.

Cashtown would also play a role in the aftermath of the battle. The inn not only served as a Confederate hospital during the battle, but as a focal point for the wagon train of wounded to guide on during the Confederate withdraw. About 4 p.m. on July 4, a column 17-miles in length, composed of wagons bearing all of the wounded, interspersed with artillery units, mounted infantry and cavalry troops, began their withdrawal through Cashtown and over South Mountain.