During the Battle of Upperville on June 21, 1863, ten thousand cavalry and infantry clashed at Vineyard Hill, then known by that name, on the fifth day of attack and counterattack along present-day U.S. Route 50 and in Aldie, Middleburg, and Upperville. Union Gen. Alfred E. Pleasonton pushed west toward the Blue Ridge Mountains while Confederate Gen. J.E.B. Stuart fought to delay the Northerners long enough to conceal Gen. Robert E. Lee’s march through the Shenandoah Valley toward Pennsylvania. The largest of these engagements unfolded at Upperville, with its most dramatic fighting at Vineyard Hill, where Stuart tried to keep Federal forces from taking the village of Upperville and the critical intersection of Ashby’s Gap Turnpike, Route 50, and Trappe Road, buying time for his hard-pressed command to reach Ashby’s Gap. Stuart directed two brigades against the advance of three Federal brigades as desperate, often hand-to-hand fighting with sabers and pistols swept back and forth across the fields under artillery fire. When his left began to give way, Stuart rode among his troopers restoring order and fighting with them, while four other brigades clashed less than a mile away. After the Confederates extricated themselves there and reached Ashby’s Gap Turnpike, Stuart ordered the last of his men to retire from Vineyard Hill.