It is hard to overstate the importance of shoes to the Confederate soldiers, who suffered as their bare feet hit the macadam highways of the North. The Confederates, also, were impressed, even awed, by the relative prosperity of southern Pennsylvania. Here was a society that possessed no slaves, yet where all the work seemed to get done. Numerous Confederates admitted they had never seen such fine-looking houses and barns as those they passed.

The shoes reared their head on June 30, 1863, when Major-General Henry Heth, of the Confederate forces saw an advertisement for fine shoes and boots from a Gettysburg store. That afternoon, Brigadier-General James Johnston Pettigrew set out with a few hundred men to investigate; as they came close to Gettysburg, along the Chambersburg Pike, they saw their first Federals. These were just a few companies of blue-coated cavalry, but Pettigrew followed his instructions—which came from Lee—to the letter. No engagement was to be entered until the Army of Northern Virginia had consolidated. Pulling back to Cashtown General Pettigrew was scolded a little by General Heth for his timidity, whereupon Heth decided to take his division of Confederates to Gettysburg the following day.