The Second Battle of Winchester
Before Gettysburg came the preparation of the route north. After the victory at the Battle of Chancellorsville, Robert E. Lee decided to move north to secure provisions for his increasingly ragged troops. As well as this practical matter, Lee hoped the move would encourage the peace activists of the north by threatening Washington, Baltimore, and Philadelphia from the west. Whilst encamped in Culpeper, Virginia with his infantry (LG Richard Ewell’s and Longstreet’s two Corps), Lee’s cavalry under J.E.B. Stuart met a large Federal Cavalry force led by Alfred Pleasanton near Brandy Station on 9 June 1863. This ended up being the largest cavalry battle of the entire war. It ended in a tactical draw, but had two significant outcomes. First, Stuart was successful in screening Lee’s force in Culpeper and the Union left the field not knowing where Lee was, but suspected he was amassing a large army on its doorstep. Second, the aggressive fighting of the Federal cavalry marked the end of Stuart’s domination of the cavalry field in the eastern theatre. The legend of the southern cavalry had been broken by excellent cavalry leaders, such as John Buford. Regardless of who won at Brandy Station, Lee’s army was still in Northern Virginia and on the move northward with determination to cause havoc.
Lee sent Ewell’s II Corps to clear the Winchester area of the Shenandoah Valley of known Union emplacements there. This was to be the route north and Lee wanted nothing slowing him down when he began his big gamble. The Union forces at Winchester were commanded by BG Robert Milroy and were significantly smaller than Ewell’s numbers. The emplacements were made up of the the “Star” fort to the west of Winchester and the main fort in the town itself. Because of the general havoc created by the advancing Confederates and the Union’s shallow numbers, Milroy had been ordered to withdrawal from Winchester to Harpers Ferry. However, after skirmishing all around Winchester on the 13th, Milroy decided to try to hold the town. This decision would later get him relieved of command, but the Confederates would relieve him of many of this troops before then.
On the 14th of June, Ewell began in earnest by sending Jubal Early’s Division to take the Star Fort during the day and increasing pressure on the main fort into the evening. As the Confederates closed on Winchester, Milroy was starting to think better of his option of withdrawal. After a quick counsel of war, he decided to retreat to the north. However, Ewell had anticipated this and sent Edward “Allegheny” Johnson’s division to cut him off. Johnson’s forces met Milroy’s retreat in the early morning hours of the 15th at Stephenson’s Depot on the Harpers Ferry road to the north of Winchester. Johnson created chaos around the Federals and Milroy’s command collapsed in panic. Milroy and some of his cavalry got away, but virtually all of the remaining infantry were killed or captured along with a great number of artillery, horses and supplies. By the morning of the 15th, all that was left was to mop up the stragglers.
The road was now clear for Lee to march northward with the mountains and Stuart’s cavalry as a screen. Gettysburg and destiny awaited.
Second Battle of Winchester Ride Recommendation
I’m writing about the Second Battle of Winchester, because I never miss a chance to recommend a ride in the Shenandoah Valley, especially any part of the Skyline Drive. I’ve also included some lesser known roads in West Virginia that are worth the ride. The Skyline Drive ends near Front Royal which is where Ewell staged from before the Second Battle of Winchester.
Map Credit:By U.S. War Department, The War of the Rebellion: a Compilation of the Official Records of the Union and Confederate Armies, U.S. Government Printing Office, 1880–1901. (U.S. War Department,) [Public domain], via Wikimedia Commons
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