The city of Winchester, Virginia, and the surrounding area were the site of numerous fights during the American Civil War as both contending armies strove to control that portion of the Shenandoah Valley.
Ties between Winchester and the American Civil War are considered to begin with the involvement of the city in the suppression of John Brown's Raid in 1859. Colonel Lewis Tilghman Moore of the 31st Virginia Militia of Frederick County assembled 150 militia men from the Marion Guards, the Morgan Continentals, and the Mount Vernon Riflemen in October, 1859 and moved them by the Winchester and Potomac Railroad to Harper's Ferry. Ironically, the first death of Brown's raid was Heyward Shepard, a free black from Winchester, who was buried in Winchester with full military honors. Following the raid, Judge Richard Parker of Winchester presided over the trial of John Brown, sentencing the insurrectionist to hang. One of the sons of John Brown and two other raiders (John Anthony Copeland and Shields Green) were later examined at the Winchester Medical College in Winchester as cadavers for medical training, an action for which the Federals later burned the college to the ground.
Neither Winchester, nor the commonwealth of Virginia were particularly fond of secession from the Union. Virginia was not a cotton state, and the Valley's economy and culture centered around small family owned farms producing wheat and cattle. However pro-Union sentiment was often conditional. Historian William A. Link writes:
On December 14, Robert Young Conrad, subsequently the Unionists' leader at the Richmond secession convention, composed resolutions adopted by a Frederick County meeting in Winchester. Although Northerners had launched an "insane war"against southern institutions, Frederick citizens regarded slavery "as perfectly consistent with civilization, humanity, and piety." Virginians would not "tamely submit" to any limitations of their rights. The resolutions appealed to the North to repeal obnoxious laws regarding fugitive slaves and to suppress abolitionists' activities that led "to invasions of other States, seducing slaves to abscond, harboring runaways, and otherwise disturbing the peace of sister States."