Saddles and Sabers: The Fight for Middleburg
Confederate and Union Soldier’s Belt Buckles
In June 1863, General Robert E. Lee launched his second invasion of the North, moving the Confederate Army of Northern Virginia through the Shenandoah Valley and into Pennsylvania. To screen this movement from Union detection, Lee relied heavily on the cavalry under Major General J.E.B. Stuart, who was tasked with protecting the army’s right flank and maintaining the element of surprise.
The Union Army, under Major General Joseph Hooker, sought to pierce this cavalry screen and gain intelligence about Lee’s position and intentions. To this end, Union cavalry forces under Brigadier General Alfred Pleasonton launched a series of aggressive reconnaissance missions in Loudoun County.
The town of Middleburg became the focal point of intense cavalry fighting between June 17 and June 19. On June 17, Union cavalry under Colonel Alfred N. Duffié made a bold and ill-fated advance toward the town. Despite initial success in entering Middleburg, Duffié’s force was quickly overwhelmed by a superior Confederate presence under Stuart and was forced to retreat with heavy losses.
The fighting intensified on June 18 and 19, as additional Union cavalry brigades—particularly those under Brigadier General David McM. Gregg and Brigadier General John Buford—clashed with Stuart’s troopers along the Ashby Gap Turnpike and surrounding ridgelines. The skirmishes were marked by aggressive charges, dismounted fighting, and shifting control of strategic ground, particularly high ground west of the town.
Though the Confederates managed to hold Middleburg initially, they were gradually compelled to withdraw westward under mounting Union pressure, ultimately falling back toward Upper Ville to continue the delaying action.
While tactically inconclusive, the Battle of Middleburg achieved its immediate objective for the Confederacy—delaying Union cavalry and obscuring the location of Lee’s infantry, which continued its march into Pennsylvania. For the Union, however, the battle marked a growing effectiveness of its cavalry arm, which had struggled earlier in the war but now demonstrated greater coordination, aggression, and resilience.
The Middleburg engagement, together with the related battles at Aldie (June 17) and Upper Ville (June 21), formed part of a broader cavalry campaign known as the Loudoun Valley engagements, which significantly shaped the operational landscape of the Gettysburg Campaign.
Though often overshadowed by the monumental clash at Gettysburg that followed just weeks later, the Battle of Middleburg remains a vital episode in Civil War history. It exemplifies the increasing importance of cavalry in reconnaissance and screening operations, highlights the tension between mobility and intelligence in wartime strategy, and offers insight into the maneuvering that preceded one of the most decisive battles of the war.