Screening Lee’s Advance to Gettysburg
The Cavalry Battles of 1863: Aldie, Middleburg, and Upperville
By June 17, 1863, a little more than a week after the epic cavalry battle at Brandy Station, General Robert E. Lee’s Confederate Army of Northern Virginia had managed to pass unseen into the Shenandoah Valley and begin its march north toward Maryland and Pennsylvania. General Joseph Hooker, commanding the Union Army of the Potomac, wanted desperately to learn Lee’s whereabouts and the direction of his movements. To this end, he ordered General Alfred Pleasonton to move his cavalry corps into the passes of the Blue Ridge Mountains to find the missing Confederates. “Drive in his pickets,” Hooker ordered. “It is better that we lose men than to be without knowledge of the enemy.”
To counter Union scouting attempts, General J.E.B. Stuart entered the Loudoun Valley with his cavalry, determined to deny access to the passes to his Union counterpart. The highway of most concern to him was the Ashby’s Gap Turnpike (modern Route 50), which ran from Fairfax to the Shenandoah Valley by way of southern Loudoun and northern Fauquier counties. At the same time, however, he had to block the approaches to Snicker’s Gap to the north. The fact that the best roads leading from the south to both gaps intersected in Aldie made this quiet little mill town a vital piece of real estate for both armies.
Judson Kilpatrick’s brigade of Union cavalry reached Aldie around 2:30 on the afternoon of June 17 to be met by pickets from the 6th Virginia Cavalry who had been ordered to guard the intersection of the Little River Turnpike and the Carolina Road (modern Routes 50 and 15, which intersect at Gilbert’s Corner). The brief exchange of gunfire was a shock because Pleasonton thought Stuart was west of the Blue Ridge; nevertheless, Kilpatrick quickly ordered two companies of the 2nd New York Cavalry to attack and drive the enemy through the town. As the New Yorkers galloped through the village, they were met by Col. Thomas Rosser and the 5th Virginia Cavalry coming from the other direction. After a short, but nasty, saber fight, both sides withdrew to assess the situation. Neither had expected to fight in Aldie.
Col. Thomas Munford, once again commanding a brigade in Fitzhugh Lee’s absence, positioned his men astride both turnpikes, the 1st, 4th and 5th Virginia and James Breathed’s artillery battery on a ridge blocking the Ashby’s Gap road, and the 2nd and 3rd Virginia to the north guarding the road to Snicker’s Gap. Munford went with the latter, leaving Colonel Williams Wickham in command of the troops on the right flank. The first phase of the battle began to play out when Rosser posted Capt. Reuben Boston and approximately 50 men of the 5th Virginia along a ridge some 600 yards in front of the main Confederate line. They immediately came under fire from the guns of Capt. Alanson Randol’s combined Batteries E and G, 1st U.S. Artillery (the same guns that would open the Battle of Gettysburg two weeks later). For a short time, they were answered by two of Breathed’s guns posted in an orchard behind Boston’s position; but the Confederate guns soon pulled back to the more distant main position.
Boston was then attacked by the 2nd New York Cavalry, but easily repulsed them, inflicting heavy losses. Kilpatrick, who would commit his forces to the fight piecemeal all day, then sent the 6th Ohio to their assistance. After a bloody fight, the two regiments forced Boston’s small detachment to surrender. It was the first time a company-size body of Stuart’s troops had ever surrendered on the battlefield. Boston would spend nine months as a prisoner of war, only to face a court-martial when he returned to Virginia. The court, however, would find him innocent and rule that the blame for his surrender was Rosser’s for placing the men too far forward to be adequately supported by the rest of the regiment.
Boston’s surrender ended the fight along the Ashby’s Gap Turnpike. The action now shifted to the north, where dismounted Confederate sharpshooters posted behind stone walls awaited an attack by the 1st Massachusetts Cavalry. About the same time the New Yorkers first attacked Boston, Maj. Henry Higginson led a squadron (two companies) of the Bay Staters north on the Snickersville Pike. For the next three hours, the fighting along the road would see-saw back and forth as the 1st Massachusetts, later supported by the 4th New York and the 1st Maine, traded shots and saber blows with the 2nd, 3rd, 4th and 5th Virginia regiments and one of Breathed’s cannon. Attacking down a narrow road bordered on both sides by high stone walls, one Union squadron after another galloped around a blind curve only to find the road filled with dead and wounded men and horses. By the time it was over, the 1st Massachusetts had suffered more than 200 casualties, the severest losses experienced by any Union cavalry regiment on a single day in the entire war.
Munford always considered Aldie to be a Confederate victory, but as darkness began to fall that night, he withdrew from the field in obedience to an order from Stuart, who had problems of his own in Middleburg.