The Battle of Upperville took place in Loudoun County, Virginia on June 21, 1863, during the Gettysburg campaign of the American Civil War.
The Union cavalry made a determined effort to pierce Confederate Maj. Gen. J.E.B. Stuart's cavalry screen. Stuart had been fighting a series of delaying actions in the Loudoun Valley, hoping to keep Union General Alfred Pleasonton's cavalry from discovering the location of the main body of Robert E. Lee's Army of Northern Virginia, much of which was in the Shenandoah Valley just west of the small village of Upperville. Stuart had slowed the Federals in fighting at Aldie and Middleburg, using ravines, creeks, and stonewalls to his advantage as he slowly withdrew westward. He made another determined stand near Upperville and succeeded in preventing the Federal cavalry from entering the Shenandoah Valley.
Following the fighting at Middleburg on June 19, a heavy rainstorm during the night had soaked the Loudoun Valley, ending a six-week drought. In the downpour, Wade Hampton's brigade of Confederate cavalry had reinforced J.E.B. Stuart and was deployed near Beverly Robertson's brigade along the Ashby's Gap Turnpike. John R. Chambliss's brigade moved northward and joined "Grumble" Jones near Unison, Virginia. Thomas T. Munford's brigade was still farther north, guarding access to the Snickersville Gap. John Mosby's partisan rangers scouted the Union positions and provided much needed intelligence on their movements.
Union cavalry commander Alfred Pleasonton, frustrated by Stuart's excellent usage of dismounted cavalry hiding behind stone walls, on June 20 asked for and received infantry support from Maj. Gen. George G. Meade's V Corps. Pleasonton had still not located Lee's main body, a task that the War Department continued to prod him to accomplish. Trying to maneuver Stuart out of position, Pleasonton sent Judson Kilpatrick's brigade along the Ashby's Gap Turnpike, supported by Col. Strong Vincent's brigade of infantry, with David McM. Gregg's cavalry division in reserve. John Buford's division would try to turn the flank.
Stuart, determined to rest his weary men on the Sabbath, did not get his wish, as Federal artillery opened up on his position around 8:00 a.m. on June 21. After initially holding off Kilpatrick's cavalry, Stuart, effectively using stone walls and steep ravines and creeks, began to fall back under pressure from the Union infantry. He made a stand west of the hamlet of Rector's Crossroads along the stone bridge over Goose Creek, where for two more hours he was able to withstand repeated Federal attacks from mounted cavalry, as well as the 16th Michigan Infantry, which sent skirmishers and sharpshooters forward to pick off the Confederate gunners.
The American Civil War (1861–1865) was the deadliest conflict in American history, killing an estimated 620,000 to 750,000 soldiers and an unknown number of civilians. The Confederate States of America, formed by eleven seceding Southern states, faced the Union in four years of warfare across 23 states and territories. Major engagements included First and Second Bull Run, Antietam (the bloodiest single day in American history, September 17, 1862), Chancellorsville, Gettysburg (July 1–3, 1863), Vicksburg (surrendered July 4, 1863), and Sherman's March through Georgia and the Carolinas (1864–1865). President Lincoln issued the Emancipation Proclamation on January 1, 1863, transforming the war's stated purpose to include the abolition of slavery and enabling the enlistment of approximately 180,000 Black men in the United States Colored Troops. Confederate General Robert E. Lee surrendered to Ulysses S. Grant at Appomattox Court House on April 9, 1865. The war resolved the question of secession and ended American slavery, though Reconstruction would face sustained resistance in its attempt to secure civil rights for formerly enslaved people.
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