Men from the town and surrounding Frederick County left their dinner tables and plows, and headed to Harpers Ferry to seize the Federal armory there and guard the northern approaches to the Shenandoah Valley. Local volunteers formed four companies of what would eventually become the renowned Stonewall Brigade. They and the other enlistees from the valley would harden into resilient but highly individualistic soldiers. Their cavalry especially was notoriously undisciplined. These valley men would spend much of the war on familiar ground. 'In few wars have the soldiers maintained as intimate contact with their homes and with the community from which they came as did the valley soldiers,' one historian writes.

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In March 1862 Winchester experienced its first enemy occupation. Major General Thomas J. 'Stonewall' Jackson's 3,500 Confederates, who had held the town since the previous summer, retreated after a sharp clash with Brigadier General James Shields's 9,700 Federals at Kernstown, to the south. Six more local men were dead, and the streets of Winchester were suddenly crowded with blue uniforms. The Union commander, Major General Nathaniel P. Banks, imposed a strict curfew on the townspeople, and food, hay, and grain were confiscated to feed the Northern troops and horses. Daily life was ruled by provost marshals. The strictures of the occupation hardened secessionist sentiment and tipped many fence-sitters to the Southern cause.

The Battle of Kernstown provided the townswomen with their first exposure to the grisly aftermath of combat. Diarist Cornelia McDonald described how she hurried to the courthouse to help tend the wounded, avoiding the bodies of several dead soldiers on the steps. Inside she found 'many, many poor sufferers, some so dreadfully mutilated that I was overcome by the sight.' When a doctor asked her to wash the wounds of a soldier whose eyes and nose had been shot away, she became faint. 'I could only stagger towards the door,' she wrote. On her way out, her dress brushed against a pile of amputated limbs.

Some of the occupying soldiers made the mistake of trying to ingratiate themselves with the Confederate women of the town. 'We are glad to hear that they are very much disappointed in their reception here,' Laura Lee wrote in her diary. 'They say they were never treated with such scorn as by the Winchester ladies.' One trooper commented to an elderly black woman about the beauty of the town's young women. 'Honey,' she replied, 'they could just cut your hearts out.'

The women noticed a change in themselves as they struggled to keep their households afloat and hold their own against a military rule that paid scant attention to their constitutional rights. Accustomed to being treated as delicate feminine ornaments, they found they had a tougher side. 'I take it out in cussing,' wrote 18-year-old Kate Sperry in her diary. 'Have become reckless–stonehearted and everything, hard and pitiless.'

'My contempt of the Yankees is so great that I cannot feel afraid of them,' wrote Mary Greenhow Lee, who fought a one-woman war against the Union occupiers and recounted it in a voluminous diary, the most detailed account of wartime civilian life in Winchester. 'I know I can cow them and make them afraid of me whenever we come into collision.'

Women would cross the street or step off sidewalks into the mud to avoid brushing up against Federal soldiers or walking under a U.S. flag. Mary Lee described how she would watch a Federal officer approach her, intending to speak, and then turn her back just as he opened his mouth. Unionist Julia Chase described the 'Jeff Davis bonnets' worn by secessionist women to hide their faces from Federal soldiers. 'They put on many airs and frowns and sneers, and try in every way to put down the Union people,' she wrote. 'They are certainly very bold and impudent.' U.S. Secretary of War Edwin M. Stanton summed up his impression of the town after a brief visit: 'The men are all in the army,' he wrote, 'and the women are the devil.'

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