"One result of incalculable importance certainly did follow this battle, - it made the Federal cavalry. Up to that time confessedly inferior to the Southern horsemen, they gained on this day that confidence in themselves and in their commanders which enabled them to contest so fiercely the subsequent battle-fields of June, July, and October." - Major Henry B. McClellan, JEB Stuart's adjutant general

In early June 1863, the Confederate Army of Northern Virginia occupied Culpeper, Virginia, and after their victories at Fredericksburg and Chancellorsville against armies twice their size, the Confederate troops felt invincible and anxious to carry the war north into Pennsylvania. One of the proudest was iconic cavalry leader JEB Stuart, who had filled in admirably for the mortally wounded Stonewall Jackson the previous month at Chancellorsville. Back in command of the cavalry, Stuart bivouacked his men near the Rappahannock River, screening the Confederate army against surprise Union attacks.

Buoyed by his recent successes, Stuart held a field review on June 5, but when Lee couldn't attend that one, he held another one in Lee's presence on June 8. During that one, the Confederates paraded nearly 9,000 mounted troops and four batteries of horse artillery for review, which included mock battles near Brandy Station. Some of the cavalrymen and newspaper reporters at the scene complained that all Stuart was doing was "feeding his ego and exhausting the horses", and he was referred to as a "headline-hunting show-off". Meanwhile, Union Army of the Potomac commander Joseph Hooker interpreted Stuart's presence around Culpeper as a precursor to a raid on his army's supply lines.