The Battle of Upperville

The idea of using all branches of the military in a coordinated, concerted fashion during offensive and defensive military operations is at the very heart of current American military doctrine. The idea of using terrain to one’s best advantage and trading ground for time, i.e. falling back or advancing depending on the ground and the opponent’s action; and fighting the enemy where he is weak rather than holding any particular piece of ground are fundamental concepts of maneuver warfare. Somewhat surprising is that these “modern” concepts were used by both Union and Confederate forces during a four day battle which raged up and down Route 50 between Aldie, Middleburg and Upperville in June 1863.

Beginning only seven days after Brandy Station, on 17 June 1963, Confederate cavalry clashed again with the Army of the Potomac’s cavalry along Route 50 between Aldie and Upperville during a running battle. J.E.B. Stuart’s horsemen had the mission of covering the Army of Northern Virginia’s movement north for Robert E. Lee’s second invasion of the Union. The Rebel cavalry, still smarting and recovering from their rough handling by the Yankees at Brandy Station, now determined to restore their pride and screen Lee’s army as it moved north, through the Shenandoah Valley. If the Southern cavalry screen failed, the Yankees could drive into Lee’s army and confront the Southern infantry corps piecemeal and destroy them in detail.

Early on the morning of the 17th, on orders from General Hooker, General Alfred Pleasonton, commanding the Army of the Potomac’s cavalry, deployed three brigades of General Gregg’s Second Division to Aldie, Virginia. The small crossroads village is strategically placed to cover the two roads to Winchester, the key to the Shenandoah Valley. One road passes over the Bull Run Mountains via Snicker’s Gap; the other, following Route 50, passes over Ashby’s Gap. At the time, Route 50 was called Little River Turnpike. The Yankee cavalry’s mission: Find the Rebel army. Gregg detached Colonel Duffie’s 275 man regiment with orders to follow the long way to Middleburg over the mountains via Thoroughfare Gap. Once in Middleburg, only four miles west of Aldie, Duffie would link up with Gregg, having swept the valley for signs of the Confederates.

General Pleasonton accompanied Gregg and the remainder of the command on the twenty-two mile march from the camps at Manassas. The fight began at about 2:30 p.m. when General Judson Kilpatrick’s Union Second Cavalry Brigade under Gregg, attacked General Fitzhugh Lee’s Virginians. The Southerners were temporarily commanded by Colonel Thomas Munford; Fitz Lee having been wounded at Brandy Station. Munford’s task was to guard Ashby’s Gap and its approaches. The lead regiment, Tom Rosser’s 5th Virginia, had only just arrived at Aldie and were setting up camp for the night. Confederate pickets were about one mile east of the town, when they were attacked by two companies of the 2d New York, Second Brigade. The Confederate cavalry withdrew initially and then Rosser counterattacked, bringing the action to a brief halt. Such a meeting engagement, as surprising as it was, turned rapidly into a brisk fight. However, General Gregg only had a third of his whole force available to deploy.

The lull in the action gave both sides time to deploy their available units. Munford’s Virginians set up their defense on the Adams farm west of Aldie, bringing up artillery in support on high ground to their rear. Judson Kilpatrick deployed his three regiments in attack formation, supported by artillery on high ground north of the village.

As Kilpatrick gave the order to charge the Rebels, a young Captain carrying a message from Pleasonton to Kilpatrick, joined in the cavalry charge. Riding ahead of the brigade commander, Captain George Armstrong Custer literally led the charge, shouting, “Come on boys!” As the two mounted forces met, Custer kept on riding, right into Munford’s camp. The Rebels, seeing his outlandish uniform, were unsure of which side he was on and made no attempt to capture him. Custer rode on back into Union lines without incident. Perhaps he would have been recognized had he come across his West Point roommate, Colonel Tom Rosser, commanding the 5th Virginia Cavalry, part of Munford’s command.

Munford’s dismounted Virginians used convenient stone walls, ditches and wooden fences as defensive positions against the charging Yankees. Such obstacles, a benefit to a defender, hampered the attacker making it difficult to deploy and bring up support for engaged units. The fight, reported Stuart, was one of the “most sanguinary” of the war. Despite their strong defensive position, the Confederate troopers on the Adams’ farm were open to flank attacks and were isolated from other Southern units posted further to the west. Part of Munford’s tactical challenge was to protect three roads without enough units to adequately do so. The result was that Company I, 5th Virginia was attacked on three sides by Federal cavalry. Faced with overwhelming superiority, the Virginians retreated.

Following the engagement at the Adams Farm, the Confederate cavalry took up defensive positions behind a stone wall on high ground a mile west of Aldie. The position guards the Snickersville Gap road as it climbs out of town. Supporting artillery was emplaced on the Furr farm, positioned so that it could cover not only the road, but the open sloping ground over which any deployed attacking force would have to advance. The 1st Massachusetts Cavalry regiment was decimated during this fight, channelled into a deadly killing zone with no room to maneuver and no avenue of escape. Munford’s victorious 3d and 5th Virginia troopers now had the opportunity to reverse the earlier defeat on the Adams’ farm and capture a Federal battery posted there.

After several hours, near dusk, Munford’s cavalry gave ground and fell back to Middleburg. While Union reports made the victory look easy, it was far from it. J.E.B. Stuart reported that it was Colonel Duffie’s flank threat from the south which forced Munford’s withdrawal, but more likely it was probably a combination of darkness and the remainder of Gregg’s division arriving in Aldie. The Southerners withdrew from the field to the west of Middleburg. Colonel Duffie’s cavalry arrived in Middleburg just in time to fight a brief skirmish with Munford’s rear guard.

The Union cavalry, running into stiff resistance, dismounted, using stone walls and barricades for defensive positions. Duffie dispatched a courier, Captain Frank Allen, to find General Kilpatrick at Aldie and bring reinforcements. At 9 p.m., on reaching Aldie, after extreme difficulty, Allen briefed Kilpatrick, who in turn conferred with his commander, General Gregg. Kilpatrick apparently asked Gregg to reinforce Duffie, since his own brigade was still recovering from their fight with Munford. But no reinforcements were coming. Duffie and his troopers were left on their own, for reasons which remain unclear.

That evening, Confederate Colonel Beverly Robertson’s cavalry brigade attacked Duffie’s regiment, forcing the Union cavalrymen to withdraw back south along the road which they had moved into Middleburg. But it was no rout. The Yankees put up such a stiff fight that they drew admiring comments from the enemy. Duffie’s regiment camped for the night south of Middleburg.

The next morning, near dawn, Duffie’s troopers awoke to find every route of escape blocked by Rebel troops. After trying to fight his way out to Aldie, Duffie turned back south again. Refusing to surrender, he ordered his regiment to disperse and make their way as best they could back to Union lines. At one thirty in the afternoon, an exhausted and dispirited Duffie made his way into Union lines at Centreville with four officers and twenty-seven men. The trip had been a long one. Colonel Duffie had come all the way via Hopewell to escape the Rebels. Over the next two days, five more officers and sixty men from his command made their way back to Union lines.

General Hooker, after hearing of the fight at Aldie, realized that behind Stuart’s cavalry had to be Lee’s infantry. He ordered his cavalry commander to find out where the Rebel infantry was. Pleasonton, possibly anticipating his commander’s intent, pushed his troopers on 18 June beyond Aldie on the roads towards Snicker’s and Ashby’s Gaps. The cavalry clashed all day long in a series of mounted and dismounted skirmishes, culminating in a fight for the town of Middleburg. Stuart’s cavalry gave ground and pulled back west of the town.

Stuart’s command remained dispersed, still guarding the mountain passes and screening the Army of Northern Virginia. Because he could not risk concentrating his forces and uncover one or more of the passes, the Southern commander determined to avoid a pitched battle, giving ground as needed, trading space for time.

On 19 June, the Union cavalry attacked Stuart’s cavalry west of Middleburg. General Gregg’s division, mauled at Brandy Station, suffered again at Confederate hands. The cavalry division lost 2/3 of its strength and Gregg was relieved of command, which now passed to Kilpatrick. During the battle, Union sharpshooters, possibly mistaking their target, shot Stuart’s aide, the flamboyantly dressed Stuart look alike, Heros von Borcke. Despite what appeared to be a mortal wound, von Borcke survived, but would not see action again.

J.E.B. Stuart’s troopers fell back again, despite inflicting heavy losses on the Yankees. Establishing another defensive line east of Upperville, the troopers used stone walls and wooden fences as defensive positions to meet the Union cavalry.

Generals Pleasonton and Gregg, knowing they had the elusive Stuart pinned down, with no infantry support, pressed the attack. On 20 June, Pleasonton asked General Hooker for infantry to support his cavalry and Hooker ordered General Barne’s division of Meade’s Fifth Corps to move up to Middleburg to support the horsemen. Pleasonton took the Third Brigade, under Colonel Strong Vincent, and five of his cavalry brigades forward to the west of Middleburg. The other two infantry brigades were left at Middleburg to secure Pleasonton’s line of communications and serve as a reserve.

What now developed on 21 June was a two pronged, combined infantry and cavalry Union assault on the dismounted Rebels. The fight at Upperville drove the Confederates west into Asby’s Gap. Pleasonton, savoring a tactical victory, did not press the attack and withdrew to Aldie. By trading space for time, Stuart’s cavalry had maintained an effective screen, allowing the Army of Northern Virginia to move unmolested towards another small crossroads town: Gettysburg.

The significance of this fight reflected a trend in military engagements. No longer were they one or two day affairs. The action was also not isolated, but a component of the overall campaign. The action further demonstrated how far the Union cavalry had come in terms of fighting ability. Also of note, General Pleasonton, a cavalry commander, leading regular infantry into battle, demonstrates how flexible the command structure of the Army had become. This is also representative of current military operations, reflecting a combined arms approach to operations and command.

Edwin Coddington, The Gettysburg Campaign, 76-7.

Samuel Carter III, The Last Cavaliers, NewYork: St. Martin’s Press, 1979, 161.

Coddington, 77.


Ibid., 78.

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