Aldie was a strategic location; it was where two macadamized turnpikes diverged, one leading to Ashby’s Gap in the west, the second northwest to Snickers Gap, both of which were main crossings of the Blue Ridge.
On June 17th, 1863, Gen. J.E.B. Stuart directed Col. Thomas Munford to take his 2,000-strong Confederate cavalry to Aldie, while Maj. Gen. Joseph "Fighting Joe" Hooker, commanding general of the Army of the Potomac, directed Brig. Gen. Alfred Pleasanton, Brig. Gen. David McMurtrie Gregg, and Brig. Gen. Judson Kilpatrick to lead an advance of about 1,200 troopers to Aldie. Skirmishes on Adam Farm, the Furr Farm, Ashby’s Gap, and along the Snickersville Turnpike led to a technical win for Kilpatrick’s and Gregg’s troopers, but Pleasanton had little to show for the victory, as Federal casualties for the day were severe - 305 were killed, wounded, and missing. The Confederates lost about 120 men, and Munford’s stubborn defense of the turnpikes fulfilled the spirit of his mission and bought Stuart valuable time to move in and concentrate his brigades in Loudoun Valley.