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After the Battle of Brandy Station on June 9, Gen. Robert E. Lee completed his plans to invade the North for the 2nd time. He sent Maj. Gen. Ewell's II Corps, Army of Northern Virginia, across the Blue Ridge Mountains to clear the lower Shenandoah Valley of Union troops and open a supply line to the Valley before the army crossed into Maryland. Ewell's columns converged on Maj. Gen. Robert H. Milroy's 6,900-man garrison at Winchester. The divisions of Maj. Gens. Edward "Allegheny" Johnson and Jubal A. Early approached the town from the south, while Maj. Gen. Robert Rodes's Division marched to Martinsburg by way of Berryville to hit the B & O Railroad.
After fighting on the afternoon of the 13th and the capture of West Fort by the Louisiana Brigade on the 14th, Milroy abandoned his entrenchments at 1:00 a.m. to escape a Confederate trap and attempted to retreat toward Charles Town. Johnson's division conducted a night flanking march and before daylight of the 15th cut off Milroy's retreat just north of Winchester at Stephenson's Depot. Almost 4,000 Federals surrendered after a desperate fight on the 15th.
Ewell's first victory as a corps commander demonstrated his tactical proficiency. This victory cleared the Valley of Union troops and opened the door for Lee's 2nd invasion of the North