On June 3, 1863, Gen. Robert E. Lee quietly pulled his Army of Northern Virginia out of its position behind the Rappahannock River and headed west toward the Blue Ridge Mountains, intent on using the Shenandoah Valley to move north toward Pennsylvania. Maj. Gen. J.E.B. Stuart’s cavalry successfully screened the Confederate infantry as it marched north behind the sheltering mountain ridge. The Union army commander, Maj. Gen. Joseph Hooker, had lost contact with Lee. For two anxious weeks, Hooker did not know what Lee was up to. Ordered to uncover the location and movements of Lee and his army, Hooker sent Brig. Gen. Alfred Pleasonton and his Army of the Potomac cavalry into the Virginia counties of Loudoun and Fauquier. Where was the Confederate infantry? Were the Confederates headed back towards Richmond, or were they being transferred to the Western Theater? Or was Lee headed toward the Potomac and another invasion of the North?
On the afternoon of June 17, Pleasonton’s troopers clashed with Stuart’s cavalry near the small mill town of Aldie, where the lead Union brigade of Brig. Gen. Judson Kilpatrick encountered Col. Thomas T. Munford’s Virginia cavalry troopers. At Aldie, two turnpikes led west to Ashby's Gap and northwest to Snickers Gap, while the Carolina Road, a strategic north-south transportation route, was located just to the east. Union control of the mountain gaps beyond Aldie would reveal Lee’s infantry. A furious fight erupted near the William Adam family farm, at first in favor of Munford as Federal charges were stopped and forced back by the withering volleys of dismounted sharpshooters behind stone walls. The 1st Massachusetts Cavalry was trapped on a blind curve on the Snicker's Gap Turnpike and was nearly destroyed, losing 198 of 294 men. The momentum shifted as Kilpatrick gained strength with reinforcements in the late afternoon, so Munford withdrew westward toward Middleburg, five miles to the west.
That same day, Pleasonton ordered a patrol to Middleburg. There, 280 men of the 1st Rhode Island Cavalry, under the command of French-born Col. Alfred Duffié, brushed aside the pickets outside of town and almost captured Stuart and some of his staff, who were unaware of the approach of the Federal cavalry. The Rhode Island troopers, following orders to hold the town, ambushed Confederate reinforcements sent there, but by the next morning they were overwhelmed by the 4th and 5th North Carolina Cavalry regiments. The isolated Rhode Island regiment lost 225 out of 280 men in the fight at Middleburg.
On June 19, Col. J. Irvin Gregg’s brigade of Federal cavalry was ordered to retake Middleburg and continue westward up the Ashby Gap Turnpike. Gregg’s men drove off the Confederate forces in town, but then stopped one mile to the west at a new Confederate defensive line astride the turnpike at Mount Defiance. Stuart’s position atop Mount Defiance was a strong one. Not only were the 3,200 men in the brigades of Brig. Gen. Beverly Robertson and John R. Chambliss positioned upon the high, commanding ridge, but the line was augmented by the placement of several horse artillery batteries.
By mid-morning Brig. Gen. David McMurtrie Gregg, J. Irvin Gregg’s cousin and superior, had ordered an attack upon Stuart’s position. Supported by additional cavalry forces from Kilpatrick’s brigade and Federal artillery, Gregg’s forces began their attack after a brisk artillery duel.
Cavalry troopers from the 4th and 16th Pennsylvania Cavalry engaged in a “carbine assault” against the green 4th and 5th North Carolina cavalry regiments south of Mount Defiance. Troopers from the 1st Maine and 10th New York attacked up the Ashby Gap Turnpike. The powerful Union assault led to the momentary capture of the Confederate guns near the summit, but a quick counterattack by the 9th Virginia Cavalry drove back the Federal troopers.
On the Confederate southern flank, the hard-pressed North Carolinians began to give way and Stuart and several of his staff officers rode amidst the retreating troopers. As they emerged from a wood line, the group was taken under fire and Maj. Heros von Borcke, Stuart’s popular Prussian staff officer, was grievously wounded in the neck and taken from the field. With the arrival of three regiments of U. S. Army Regular cavalry under Brig. Gen. John Buford threatening his left flank, Stuart smartly pulled his forces back to another ridge line along the Ashby Gap Turnpike, nearer the town of Upperville just eight miles away. Despite the intensity of the fighting at Middleburg, total casualties for both sides over two days of fighting were less than 400 men.
On June 21, Union cavalry made another determined effort to pierce Stuart’s cavalry screen. Two days after skirmishing in and around Middleburg, Brig. Gens. Wade Hampton and Robertson’s brigades made contact with Gregg’s division at the turnpike bridge over Goose Creek, four miles east of Upperville. Gregg called for infantry support, and received the brigade of Col. Strong Vincent from the Fifth Corps.
Vincent's infantrymen pushed the Rebel troopers back to Vineyard Hill outside Upperville, and his 16th Michigan Infantry captured an artillery piece from Stuart's fleeing men. John Buford’s column detoured to attack the Confederate left flank and supply train north of Upperville along the Trappe Road, but encountered Brig. Gens. William E. “Grumble” Jones and Chambliss’s cavalry brigades. Meanwhile, Gregg and Kilpatrick’s brigades advanced toward Upperville from the east along the turnpike. After furious mounted fighting, Stuart withdrew to Ashby’s Gap in the mountains.
Over the next few days, as the cavalry skirmishing around Aldie, Middleburg and Upperville diminished, Stuart asked for and received Lee's permission to strike east and make a circuit of the Union army as it followed the Confederates toward Gettysburg. While Union attacks against Stuart’s cavalry along the turnpike were generally successful, Stuart’s expert parrying of various Federal probes prevented Pleasonton’s forces from directly observing or interdicting the movement of the Army of Northern Virginia towards Maryland. In five days of fighting, both sides counted about 1,400 casualties.
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