Date: June 21, 1863
Troops Engaged: 5,500 US; 6,000 CS
Casualties: 209 US; 180 CS
The Battle of Upperville began where the Battle of Middleburg left off. Stuart formed his line on high ground but after the Union troops attacked, Stuart retreated and lost a piece of artillery—the first he lost in the war. The Confederates withdrew further along the turnpike and formed another line to prevent Federals from crossing Goose Creek. For several hours the Confederates held off their opponents but were finally forced to withdraw further west. The Confederates staged an admirable fighting withdrawal, making stands at Vineyard Hill, just east of Upperville, and Trappe Road, just west of town. Although pushed back considerably, Stuart fell back to and held Ashby Gap in the Blue Ridge Mountains. Lee’s infantry remained secure in its march north.
UPPERVILLE, MIDDLEBURG, AND ALDIE TODAY
These three battles occurred along the Ashby Gap Turnpike, or modern Route 50. Many of the landmarks and structures from these battles are still standing and utilized today. A historic stone bridge in Aldie still spans the Little River on Route 50, and the Adam, Furr, and Bittersweet farms are also standing and occupied today. Across the street is a cemetery in which are buried some of the casualties of the Battle of Upperville, including native resident, J. Warren Brent. You can also still visit the natural resources from the battles. Mount Defiance, Stuart’s initial defensive position at Middleburg, is located just west of town. Goose Creek, much fought over during the Battle of Upperville, still runs nearby today. And Routes 50 and 17 will take you through Ashby’s Gap in the Blue Ridge Mountains.