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Maj. Gen. Robert Milroy was convinced his Winchester forts were impregnable. He was wrong.

WHEN UNION MAJ. GEN. ROBERT H. MILROY marched his division of approximately 7,000 men into Winchester, Va., on New Year’s Day 1863, he saw the unseasonably warm weather as an omen he had been ordained to enforce the Emancipation Proclamation and “clear way the storm and tempests of war occasioned by that mighty curse, slavery.” In addition to enforcing emancipation, however, Milroy had another mission in the strategically situated, oft-contested community of Winchester: protecting the Baltimore & Ohio Railroad. Milroy initially believed the best way to perform his duties as part of Maj. Gen Robert Schenck’s Middle Department was to move south, up the Shenandoah Valley, and secure as much territory as possible. But Milroy’s immediate superior, Brig. Gen. Benjamin F. Kelley, disagreed. Convinced any significant movement south might provoke a Confederate assault, Kelley requested that Milroy “make no aggressive movement, but fortify as best you can and hold Winchester.”

Although Milroy was aggressive, as evidenced by his conduct during fighting at McDowell and Second Bull Run, he concurred with Kelley’s view. “The Gray Eagle”— the affectionate nickname Milroy’s men had given him— believed strengthening Winchester’s defenses would send a clear signal to Confederate sympathizers, as well as to area Unionists and African Americans who benefited from his occupation, that the United States “Government had firmly re-established its power” in the region.

Milroy and his officers realized the city could not be easily guarded. An Ohio officer in his command wrote: “Winchester…presents no front to the enemy but can be approached from any or every direction…I would rather be on the outside.” Regardless of the difficulties, Milroy knew Winchester must be protected. Nearly two weeks after the general’s arrival Captain Albert S. White, commanding the Independent Company of Engineers, arrived in Winchester at Kelley’s behest to assist him. On January 17, White inspected the town’s defenses and commented that the “works already erected for the defense of said town…are of great strength, and command the town and approaches.” Despite White’s overall positive assessment, however, he recommended that some of the defenses be repaired, strengthened and expanded.

White recommended that Milroy focus his construction efforts on three fortifications—Fort Garibaldi, the West Fort and the Star Fort. Fort Garibaldi, renamed Fort Milroy (and sometimes also referred to as the Flag Fort or the Main Fort), had been constructed earlier in the war by troops under Maj. Gen. Nathaniel P. Banks and only needed repairs. The West Fort, northernmost of the fortifications, would be new, as would the Star Fort—which would be built on the site of a series of gun emplacements earlier constructed by Confederate troops and dubbed Fort Alabama.

As Milroy and his engineers were considering improving Winchester’s defenses, he decided the commanding ground occupied by Fort Alabama offered a prime setting to create a star fort—a fortification style the general believed, thanks to his education at Captain Partridge’s Military Academy in Norwich, Vt., was “the most useful and safest kind.” One of Milroy’s veterans observed that the ground upon which the new fort would stand “overlooked the lower hills and ridges…from Star Fort there was a wide and beautiful prospect over the town; over the fields and woodlands to the north.”

By the third week of January, Milroy’s troops had begun working on the fortifications. He established a seven-day rotation, where his men spent three days on guard duty, three days performing camp chores and one day each week laboring on the defenses. This meant each day approximately 1,000 men were at work on the fortifications. Despite Milroy’s attempts to lighten their load, the soldiers found the construction grueling and physically exhausting. A veteran from the 18th Connecticut explained that it was “severe duty…working on the fort and rifle pits, with axe, pick, and shovel…[at] the Star Fort. Many of the boys had never used or handled that kind of tool. It was hard work.”

Building the Star Fort proved to be a doubly rewarding project for Milroy. In addition to strengthening Winchester’s defenses, the new fortification would be constructed using limestone from Selma, the home of Senator James Mason, author of the controversial 1850 Fugitive Slave Law. On January 20, 1863, Milroy—an ardent abolitionist—ordered the house, which had already been significantly damaged during Banks’ occupation, pulled down and the stone from it used in constructing the new structures, including the gun platforms in the Star Fort. “Today the walls of Mr. Mason’s house were pulled down,” wrote Winchester resident Cornelia McDonald, adding, “They have taken the stones of Mr. Mason’s house…to build the fortifications.” Preliminary archaeological investigations at the Star Fort—today the best preserved and the only publicly accessible defenses built under Milroy’s command—have revealed significant quantities of cut limestone that presumably came from Mason’s home.

To many of Winchester’s residents, fortifications such as the Star Fort symbolized Milroy’s oppressive regime, but to Unionists and African Americans living in the area they offered security and the hope of permanent Union control. For Milroy and some of his men the forts also inspired a sense of invincibility. “The position…[was] very well chosen and formidable,” recalled one Ohio veteran. In Milroy’s own estimation, the improved defenses offered him the opportunity to defeat a Confederate force at least three or four times his division’s strength.

Milroy might have possessed limitless confidence in Winchester’s defenses, but Union General in Chief Henry Halleck did not. Beginning early in the spring of 1863, Halleck feared for Milroy’s safety, and he urged both Milroy and Schenck to evacuate the town, warning them, “that is no place to fight a battle.” Halleck’s anxiety increased as General Robert E. Lee’s Army of Northern Virginia marched north after its smashing success at Chancellorsville. Reports from Milroy’s scouts also stirred consternation, since intelligence sources indicated the lead elements of Maj. Gen. Richard Ewell’s Second Corps were preparing to strike Milroy on June 10.

 Milroy was certainly not prepared to give up Winchester without a fight. General Schenck supported Milroy’s decision to remain, but told him to make preparations for a withdrawal and remain alert. In the days leading up to June 10, Milroy ordered all the trees around the forts cleared, to improve visibility. Commenting on Milroy’s preparations in early June, Winchester resident Mary Greenhow Lee noted, “The Yankees are in a panic; the horses are kept to the guns…ready to go at any moment; Milroy is in a rage.”

June 10 came and went without incident, perhaps lulling Milroy into a false sense of security. But on June 12 the van of Ewell’s Corps appeared about 10 miles south of Winchester in Middletown. The following day Ewell’s command pressed Milroy’s brigades from Kernstown to Winchester’s southern outskirts. After nightfall on the 13th—during a terrible storm that interfered with telegraph communications with Baltimore and Washington, D.C.—Milroy ordered his command to take refuge inside the three fortifications they had built.

Throughout the day on June 14, the Union forces waited for Ewell to attack. After a flanking maneuver of approximately 10 miles, Confederates from Maj. Gen. Jubal Early’s Division prepared to strike the smallest of Milroy’s three fortifications, the West Fort. Following a 45-minute artillery barrage from the 20 cannons of Lt. Col. Hilary P. Jones’ Battalion that started around 5 p.m., Brig. Gen. Harry T. Hays’ Louisiana Brigade spearheaded an assault that captured the West Fort.

After Hays’ success, Jones’ gunners opened fire, initially focusing mostly on Fort Milroy—which contained the bulk of Milroy’s division and served as the general’s headquarters throughout that day. This puzzled the Union artillerists from Captain Frederick W. Alexander’s Baltimore Light Artillery who were defending the Star Fort. One gunner noted: “In the early part of the fight the enemy seemed to ignore the Star Fort occupied by our battery, and…concentrated their fire on other parts of the field.” But once the artillerymen fired a shot that struck one of Jones’ guns, the Confederate batteries turned their attention to the Star Fort.

The incessant artillery barrage against Alexander’s men, which included “an allotment of railroad iron,” prompted them to fire rapidly, even while Rebel shells burst over the gunners’ heads and crashed, as one artillerist recorded, “against the opposite side of the parapet” or burrowed “in the earthworks at our front.” Artillerist Frederick Wild recalled: “Our little Lieutenant Peter Leary…whom the boys did not think much of…took a hand in loading and firing a cannon in his shirt sleeves; cheering and hurrahing at every successful shot; and there were many.”

The cannoneers’ accuracy—which compelled the Confederate gunners in West Fort to pull back from their position three times during the artillery duel—inspired Milroy’s men. A Union veteran from Colonel Andrew McReynolds’ brigade recalled: “The guns in the Star Fort greeted them with shell after shell planted among them with astonishing precision, and each one as it burst in the ranks of the enemy was followed by exulting cheers from the Union troops.”

While most of Alexander’s fire struck the Confederates in the West Fort, some of their shots landed short of the para pet walls and hit property adjacent to that fortification—including houses. Among those damaged was a home built of limestone belonging to Dr. William Fahnestock and his wife Mary, who were caring for wounded soldiers from both sides. Chain shot from the cannons in the Star Fort tore through the roof of the stately dwelling.

The Union artillerists had to cope with incessant fire from Jones’ guns, which took a terrible toll on the battery’s horses. Wild noticed that a piece of Confederate shrapnel tore out a piece of a “beautiful black wheel horse[’s]… throat.” Knowing that nothing could be done to save the animal, Wild led the horse out of the fort, along with several other wounded horses, “where the leaden hail soon finished them.”

 As darkness descended, the Confederate artillery fire slackened. During that lull the 6th Maryland Infantry—which had spent much of the day in the rifle pits around the Star Fort with the 67th Pennsylvania—entered the fortification to provide additional support to the Union guns. No sooner had the 6th gotten into position than the Federals spied what they believed were preparations for a Rebel infantry assault (Confederate accounts don’t mention such a planned attack that night). In response, the Yankee cannon belched forth “grape and canister” while the infantry blazed away in what one of the Federal veterans regarded as a splendid “display of pyrotechnics, that was, awfully! Terribly, grand!” After the defenders eliminated any threat of a potential assault, real or imagined, both sides ceased fire for the night.

By that time Milroy had realized the fruitlessness of defending Winchester. During a late-night council of war the Gray Eagle told his division to evacuate, ordering the guns to be spiked and all efforts made, in the words of Captain Alexander, “to retire” and maintain “the most perfect silence and secrecy.” Shortly after 1 a.m. the remainder of Milroy’s division quietly set out for Martinsburg. Several miles north of the fortifications, however, Maj. Gen. Edward “Old Alleghany” Johnson’s division surprised Milroy’s veterans, cementing Ewell’s success in the Second Battle of Winchester.

Winchester’s Confederate civilians reveled in Ewell’s victory, delighted to see Federal prisoners—along with some Unionist civilians—held captive in the same fortifications that had once enabled members of Milroy’s division to feel as if they were “in a safe place.” Mary Greenhow Lee confided in her diary, “it is glorious for us now.”

Mary Lee’s euphoria would be brief. The Confederate Army suffered a crushing blow at Gettysburg the following month. Less than three weeks after writing she was “almost painfully happy” with Ewell’s success at Winchester, she faced the grim reality that General Lee’s defeat in Pennsylvania ensured Winchester’s Confederates would likely “be again left to the fury of the Yankees.”


Jonathan A. Noyalas is director of the Center for Civil War History at Lord Fairfax Community College. He also recently served as the Hugh and Virginia McCormick Visiting Chair in Civil War History at Shenandoah University.

Originally published in the December 2014 issue of Civil War Times. To subscribe, click here.