Ten thousand Confederate troops filled the small town of Winchester, Virginia, early in the summer of 1861. Soldiers were quartered in almost every building. Then, in mid-July, a call came to stop a Federal advance on Manassas, and the town quickly emptied. The streets grew quiet.

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Two days later the quiet was broken by the clatter of horse-drawn wagons carrying wounded and dead soldiers back from the First Battle of Manassas. Five of the dead were townsmen. 'I saw the rough farm wagons that brought them back in rough boxes through the straw in the bed of the wagon,' wrote resident Robert T. Barton. 'We had begun to realize what war was.' And the next four years wouldn't let them forget.

No town heard more of the war's rumblings than Winchester. Several major engagements were fought in the vicinity, including the namesake First, Second, and Third Battles of Winchester in May 1862, June 1863, and September 1864. There were also dozens of smaller skirmishes and raids. All this action has led some local historians to claim that military control of the town switched hands nearly 100 times, though a recent tally of formal changes of possession sets the number at 14.

Winchester was a prosperous commercial center of 4,400 people that lay at the junction of several roads, including the macadamized Valley Pike. The main street through town featured an imposing Greek Revival courthouse, gas lights, solid brick shops, taverns, and the two-story Taylor Hotel. The inhabitants were hard-working, sociable churchgoers. The surrounding fields of fertile limestone soil supported lush wheat crops. Abundant pastures fattened the valley's cattle and sheep, and gave the people a diet rich in meat.

The town's location determined its fate in the war. Tucked in the northern stretches of the Shenandoah Valley, the town lay on a natural transportation corridor used first by nomadic American Indian tribes, then by westbound settlers, and finally by Confederate armies, which found it advantageous to march north behind the barrier of the Blue Ridge Mountains to the east. Both Confederate invasions of the North followed this route. Winchester was also close to key military sites. About 70 miles from the U.S. capital, Washington, D.C., and 20 miles from the important Baltimore & Ohio Railroad at Harpers Ferry in western Virginia, the town was a natural jumping-off point for Confederate army campaigns.

Another geographic feature would magnify in importance during the war: Winchester was surrounded on all sides by low hills that hid the approach of armies. Occupiers found it almost impossible to mount a defense, so they usually had to flee quickly, sparing the town from prolonged, destructive sieges.

The irony of Winchester's experience is that the townspeople were reluctant to go to war. Established in the 18th century by Scottish and German settlers from Pennsylvania, the town and its surrounds were populated mostly by small-scale farmers, artisans, and merchants, who had little use for slaves and who retained strong ties to the North. Thus they had sharp political and cultural differences with the slaveholding tobacco planters of eastern Virginia who dominated the statehouse.

When Virginia held its secession convention in April 1861, Winchester sent Robert Y. Conrad, a level-headed businessman and lawyer who ended up leading the Unionist faction. Conrad, along with many other representatives, fought hard against secession with the hope that the North and South could reconcile. On April 4 the convention voted 89 to 45 to remain in the Union. But when secessionist forces bombed Fort Sumter, South Carolina, on April 12 and President Abraham Lincoln called three days later for 75,000 volunteers to fight 'the insurrection,' the tide began to turn. 'Lincoln's awful proclamation has made secessionists of all,' one Winchester woman wrote. The representatives voted again, on the 17th, and everyone had changed his mind except Conrad and six other delegates from the northern Shenandoah Valley. Nonetheless, Conrad and most of Winchester accepted the decision to secede. Conrad's four sons would serve with the Confederacy.

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