The Union occupiers made their own contributions to the tense atmosphere. For instance, officers forced residents to sign an oath of allegiance to the United States as a condition of free movement and other privileges. Some refused to sign, even later when obtaining necessities such as food and firewood was contingent on the oath.

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Of course, not every interaction between occupier and occupied brimmed with such hostility. The women who carried food to the many hospitals fed both Northern soldiers and Southern prisoners, and Federal officers sometimes detailed guards to homes whose residents had been harassed. Some Unionist women even married Northern soldiers (though a few would later discover that their new husbands already had wives and families in the North).

The town's first occupation came to abrupt end in late May, when 17,000 hard-marching troops under Stonewall Jackson suddenly stormed out of the Luray Valley to the south. Most of Banks's force was in nearby Strasburg, leaving only 6,000 men in Winchester. Banks backpedaled his main contingent furiously and had barely got his men into position on the south hills when the boom of Jackson's artillery at dawn on May 25 opened the First Battle of Winchester. The Federal lines soon broke, and civilians watched with glee as their occupiers fled through the streets panic-stricken. A few townspeople took potshots at the retreating Federals, including a woman who leaned out a window to fire a pistol at a galloping cavalryman.

The dramatic liberation was the high point of the war for Winchester. Jackson's troops were welcomed as conquering heroes. Even dour Jackson was swept up in the celebration. The people'seemed nearly frantic with joy,' he wrote his wife. 'Our entrance into Winchester was one of the most stirring scenes of my life.'

But jubilation turned to sorrow in some homes as news of deaths arrived. At the Barton home on Market Street, the family gathered around the body of Marshall Barton, a handsome artillery officer who had been killed by a shell.

The town's Unionists were shocked by the rout of their troops and the riotous cheering of the secessionists. 'Oh, what an awful day this has been!' wrote Julia Chase. 'God grant I may never see the likes again. The citizens in town have become demons almost. It is said that Rev. Norval Wilson fired upon a Federal soldier. God have mercy on this town.'

The secessionists' celebration was short-lived. Jackson's bold foray in the valley wrecked Union plans to link Major General George B. McClellan's Army of the Potomac, positioned east of Richmond, with another force under Brigadier General Irvin McDowell, marching south from Washington, for a concerted drive on the Confederate capital. Now the Northern capital seemed threatened, and Lincoln set three separate forces into motion to trap Jackson. After seizing a hoard of Union supplies at Harper's Ferry, Jackson moved back south through the valley, eluding and defeating his pursuers. Winchester was left deserted, exposed, and grief-stricken over the loss of cherished hero Turner Ashby, a cavalry commander killed in a rearguard action near Harrisonburg in early June, just two weeks after a promotion to brigadier general.

With memories of their treatment in Winchester just two weeks before still fresh, returning Federal troops were not in a forgiving mood. They searched and looted homes, ransacked stores, and roughed up citizens. The situation got so bad that Banks ordered his army out of town and sealed off the flow of mail and contraband. Federal artillerymen practiced their trade by firing wooden cannonballs over the town. A few fell short and hit houses, suggesting the damage that could occur with live ammunition.

After a long and difficult summer, Winchester braced itself for another battle as General Robert E. Lee marched his Army of Northern Virginia into the valley after the Second Battle of Manassas in August 1862. Once again the town was spared when the heavily outnumbered Federals fled without a fight, but the Union troops sent a bolt of terror through the population by burning several warehouses and detonating a powder magazine with a blast that shook every house to its rafters and broke many windows.

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