In June 1863, Gen. Robert E. Lee led the Army of Northern Virginia through gaps in the nearby Blue Ridge Mountains and into the Shenandoah Valley to invade the North. Maj. Gen. J.E.B. Stuart’s cavalry corps screened the army from Federal observation. Union cavalry commander Brig. Gen. Alfred Pleasonton attempted to break through Stuart’s screen and fought three sharp engagements along this road: the Battles of Aldie on 17 June, Middleburg on 19 June, and Upperville on 21 June. Under Pleasonton’s pressure, Stuart fell back westward but kept the Federal cavalry east of the gaps.
