Second Battle of Winchester

In June of eighteen sixty-three, Robert E. Lee set his Army of Northern Virginia in motion northward for the second time, aiming for Pennsylvania. To reach the Potomac he needed to clear the Shenandoah Valley, and standing in the way was a Union garrison of about seven thousand men under the stubborn, flamboyant Major General Robert Milroy, a man who had already received multiple orders to retreat and ignored every one of them.

Milroy had fortified the hills around Winchester with a ring of earthworks: West Fort, Star Fort, and a main redoubt he modestly called Fort Milroy. He believed his position was impregnable. He was wrong about the enemy heading toward him. The force bearing down was Lieutenant General Richard Ewell's Second Corps, Stonewall Jackson's old command, now under new management but no less dangerous. Ewell outnumbered Milroy by more than two to one.

On June thirteenth, eighteen sixty-three, Ewell's men began enveloping the Union fortifications. Jubal Early took a division on a flanking march that swept around to the west and overwhelmed West Fort in a sharp evening assault on the fourteenth, capturing its guns and shattering Milroy's confidence along with his defensive ring. Milroy ordered a nighttime withdrawal, but Ewell had anticipated that. Major General Edward Johnson moved a division to block the Martinsburg Pike, the only practical escape route, and when Milroy's retreating column collided with that blocking force at Stephenson's Depot before dawn on June fifteenth, the result was a rout. Roughly thirty-five hundred to four thousand Union soldiers were captured. Confederate casualties numbered only two hundred sixty-nine.

The Second Battle of Winchester was one of the most lopsided Confederate victories of the entire war. It swept Federal presence from the Valley and opened the door for Lee's northward march, the campaign that would end, three weeks later, at a Pennsylvania crossroads called Gettysburg.