Upperville
Drama at Vineyard Hill
This site, known during the war as Vineyard Hill, commands a clear view of the road, stone walls, and fields in front of you where 10,000 cavalry and infantry clashed in the Battle of Upperville on June 21, 1863. It was the fifth day of attack and counterattack along present-day U.S. Route 50 and in the towns of Aldie, Middleburg, and Upperville. Union Gen. Alfred E. Pleasonton pushed west towards 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 Battle of Upperville was the largest of these engagements, and the most dramatic aspects of that encounter took place at Vineyard Hill. From here Stuart fought to prevent the Federals from seizing the village of Upperville behind you and the critical intersection at Ashby’s Gap Turnpike (Route 50) and Trappe Road, to allow his embattled forces to reach the safety of the Blue Ridge Mountains at Ashby’s Gap.
Here Stuart directed two of his brigades as they resisted the advance of three Federal brigades. The fighting near here was desperate and often hand-to-hand, the men wielding sabers and pistols. As Stuart’s line gave way on the left, he rode among his troopers restoring order and fighting “with the men like a common soldier.” Charge and countercharge carried the men and horses back and forth across these fields under the deadly fire of artillery.
Less than a mile to your left, and visible to the men on the high ground around Vineyard Hill, four other brigades clashed, leading one Federal participant to conclude, “the panorama was one of the finest and most animating ever beheld.” Once the Confederates extracted themselves there and reached Ashby’s Gap Turnpike, Stuart ordered the last of his men to retire from Vineyard Hill.
Marker is on John S. Mosby Highway (U.S. 50), on the right when traveling east.
Courtesy hmdb.org
