The vanguard of the Confederate Army of Northern Virginia, consisting of Lieutenant-General Richard Ewell’s Second Corps, was ready to attack the Federal garrison at Winchester in the Shenandoah Valley by the night of June 14. Ewell had two divisions, led by Major-Generals Edward “Allegheny” Johnson and Jubal Early, on the south, east, and west of the town. Ewell’s force numbered about 12,500 men.
Defending Winchester was a Federal garrison of less than 7,000 men under Major-General Robert H. Milroy. Milroy had been advised to abandon the town and move his force to Harpers Ferry, but he opted to stay and defend the three forts north and west of town, convinced that they were impregnable.
Johnson’s Confederates feinted from the south and east of Winchester, while Early positioned his troops to the west. The Confederates brought up 22 guns and started bombarding the forts at 6 p.m. At 6:45, one of Early’s brigades attacked the main fort to the west, while Johnson drove against the two to the north. Early’s men captured one of Milroy’s key earthworks, and the Confederates nearly surrounded the Federals by nightfall.
Meanwhile, Ewell had sent the rest of his corps, consisting of Brigadier-General Albert G. Jenkins’s cavalry and Major-General Robert Rodes’s infantry division, to attack the Federal garrison at Martinsburg, behind Milroy to the north. Jenkins’s horsemen came up first, and although the Federals held firm against their assault, they evacuated as many supplies as they could. By the time Rodes’s troops arrived, many of the Federals had escaped. But the Confederates still took 700 prisoners, along with five guns and a large amount of supplies.
Back at Winchester, Milroy held a council of war at 9 p.m. Surrender was not an option because the Confederate government considered Milroy an outlaw, subject to execution for his suppression of civilians and liberation of slaves. The officers agreed to try to escape northeast to Harpers Ferry, via Martinsburg, along the same route Milroy had used last year to elude Thomas “Stonewall” Jackson.
The Federals were to move out at 1 a.m., but before they left, they had orders to destroy all the wagons, guns, and supplies they could not take with them. The men began heading toward Stephenson’s Depot, on the Martinsburg Turnpike, four miles north of Winchester.
Ewell, who had served under “Stonewall” Jackson, anticipated Milroy’s plan and ordered Johnson to block the turnpike at Stephenson’s Depot. This maneuver, which was very difficult to execute in darkness, took five hours. Nevertheless, the Confederates reached the depot around 3 a.m., ahead of the retreating Federals.
During this time, messages were exchanged between President Abraham Lincoln and Major-General Joseph Hooker, commanding the Army of the Potomac. Lincoln asked incredulously, “Do you consider it possible that 15,000 of Ewell’s men can now be at Winchester?” He then asked if Hooker could somehow rescue Milroy. Hooker replied, “I do not feel like making a move for an enemy until I am satisfied as to his whereabouts. To proceed to Winchester and have him make his appearance elsewhere, would subject me to ridicule.”
Lincoln cited Hooker’s own message stating that the corps of both Ewell and Lieutenant-General James Longstreet had left Culpeper Court House. If Hooker was right, then, Lincoln wrote, “I should feel sure that Winchester is strongly invested.” Secretary of War Edwin M. Stanton then informed Hooker that Ewell’s corps was divided between Martinsburg and Winchester. But Hooker still would not move.
As Milroy’s Federals approached Stephenson’s Depot, they saw the Confederates blocking their path at a bridge. Milroy directed them to fight their way through, but rather than use his numerical advantage for one overwhelming assault, Milroy sent his men against the enemy piecemeal. The Confederates scattered the Federals with artillery, and as the sun rose, Milroy ordered them to disperse. They fled in all directions as the Confederates rounded most of them up.
The Federals sustained 443 casualties and lost over 4,000 taken prisoner. Milroy escaped. The Confederates also took 23 guns, 300 wagons, 300 horses, and enormous amounts of supplies while losing just 269 men (47 killed, 219 wounded, and three missing). Ewell’s victory at the Second Battle of Winchester was greater than Jackson’s victory over Nathaniel P. Banks in the first. According to the New York Herald, “not a thing was saved except that which was worn or carried upon the persons of the troops… all the artillery… all the commissary and quartermaster’s stores… the private baggage of the officers and men, all fell into the hands of the enemy…”
In just three days, Ewell had pushed the remaining Federals in the Shenandoah Valley into Harpers Ferry and opened the path for the rest of General Robert E. Lee’s Confederate army to move north. Ewell’s men were impressed by his debut combat performance as their corps commander; Captain Charles Blackford wrote, “Ewell won his right to Jackson’s mantle at Jackson’s game on Jackson’s ground. This success will give the corps more confidence in Ewell.”
A court of inquiry later investigated Milroy’s conduct at Winchester, including his insistence on holding the town and his claim that he could withstand any Confederate attack. The court absolved Milroy of any blame for the fiasco, but he never held a significant command again.
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