Battle of Middleburg: The Cavalry Screen Before Gettysburg

In the second week of June eighteen sixty-three, Robert E. Lee's Army of Northern Virginia was moving north toward Pennsylvania. To conceal that movement, J.E.B. Stuart's Confederate cavalry screened the Blue Ridge Mountain gaps while Union cavalry under General Alfred Pleasonton probed eastward trying to determine where Lee's infantry was and where it was headed.

The result was a week of nearly continuous cavalry combat across the rolling farms and small villages of Loudoun County, Virginia. Middleburg, a small crossroads town on the Ashby's Gap Turnpike, sat directly in the path of this screening action. On June seventeenth, eighteen sixty-three, a Union cavalry brigade under Colonel Alfred Duffie pushed into Middleburg and tangled with Confederate horsemen. The following two days saw sharp fighting as Union forces under General David Gregg pressed against Stuart's screen, trying to pierce it and locate Lee's main body. Stuart's troopers gave ground grudgingly but did not break.

The skirmishing around Middleburg continued through June nineteenth. Union cavalry suffered significant casualties in repeated charges against Confederate positions on the ridges surrounding the village. Stuart's men were eventually pushed back to Upperville, where the fighting continued on June twenty-first before the Union advance was finally checked at Ashby's Gap itself.

The significance of these engagements, Middleburg, Aldie, Upperville, was strategic rather than tactical. Stuart successfully maintained the screen. Union cavalry never penetrated far enough to locate Lee's infantry columns marching north through the Shenandoah. Lee reached Pennsylvania without the Union high command having a clear picture of his army's position or strength. Three weeks later, both armies met at Gettysburg.

The farmland and stone walls around Middleburg look much as they did in eighteen sixty-three. The village has largely escaped the suburban expansion that consumed much of northern Virginia, and several of the ridges where cavalrymen fought across stone fences remain in agricultural use. The Civil War Trust has preserved portions of the battlefield.