As Lee's army moved into Pennsylvania, Stuart's cavalry screened his movements, thereby engaging in the more traditional cavalry roles, but it's widely believed that he was still smarting over the results of June 9. As a result, many historians think it likely that he had already planned to remove the negative effect of Brandy Station by duplicating one of his now famous rides around the enemy army, much as he did to McClellan's Army of the Potomac during the Peninsula Campaign in 1862. This time, however, as Lee began his march north through the Shenandoah Valley in western Virginia, it is highly unlikely that is what he wanted or expected.

To complicate matters even more, as Stuart set out on June 25 on what was probably a glory-seeking mission, he was unaware that his intended path was blocked by columns of Union infantry that would invariably force him to veer farther east than he or Lee had anticipated. Ultimately, his decision would prevent him from linking up with Ewell as ordered and deprive Lee of his primary cavalry force as he advanced deeper and deeper into unfamiliar enemy territory. According to Halsey Wigfall (son of Confederate States Senator Louis Wigfall) who was in Stuart's infantry, "Stuart and his cavalry left [Lee's] army on June 24 and did not contact [his] army again until the afternoon of July 2, the second day of the [Gettysburg] battle."

As it would turn out, Lee's army inadvertently stumbled into Union cavalry and then the Union army at Gettysburg on the morning of July 1, 1863, unaware of the force in their front. From July 1-3, Lee's army tried everything in its power to decisively defeat George Meade's Union Army of the Potomac, unleashing ferocious assaults that inflicted nearly 50,000 casualties in all. Lee would try and fail to dislodge the Union army with attacks on both of its flanks during the second day and Pickett's Charge on the third and final day.