The Shenandoah Valley was Shawnee hunting ground in the early eighteenth century, contested before that between Iroquoian-speaking Senedo peoples and Algonquian-speaking newcomers from the north. The first English-speaking settlers came south down the Great Wagon Road from Pennsylvania in 1729 - Abraham Hollingsworth, the Quaker from Maryland, was among the first. Jost Hite arrived in 1732 with ten German families and some Scots-Irish. Governor William Gooch, despite Virginia's official Anglican establishment, pursued a tolerant religious policy that drew Quakers, Lutherans, Presbyterians, and Reformed settlers in numbers that would shape the valley for generations. James Wood, an English surveyor born in Winchester, England, laid out 26 half-acre lots in 1744 around a settlement first called Frederick Town. The House of Burgesses chartered the town as Winchester in 1752 after Wood's birthplace. The Iroquois ceded their nominal claim to the valley in the Treaty of Lancaster in 1744. The Shawnee, whose chief Cornstalk had his court at Shawnee Springs just outside the modern city, moved west across the Alleghenies in 1754 under pressure from the same conflicts that became the French and Indian War.

When the French and Indian War broke out, 23-year-old Colonel George Washington made Winchester the base of his operations. Edward Braddock's expedition to Fort Duquesne marched through Winchester in 1755 with Washington as Braddock's aide-de-camp; Daniel Morgan, a future Revolutionary War general and future U.S. Congressman who lived in the town, marched with Braddock as a wagoner. In 1756 Washington designed and began building Fort Loudoun on James Wood's land in what is now downtown Winchester. The fort was completed in 1758 and remained occupied until the Revolution. While the fort was being built, Washington was elected at age 26 to represent Frederick County in the House of Burgesses. Winchester held him through three terms. Local Quakers who refused to pay war taxes were imprisoned in the town jail during this period - one of the long collisions between Quaker pacifism and Virginia's military expectations that would, by the mid-nineteenth century, leave the original Quaker majority a minority in their own founding town.

During the Civil War, Winchester sat at the strategic apex of the lower Shenandoah Valley. Seven major battles were fought within or near the city: First and Second Kernstown, First, Second, and Third Winchester, Cool Spring, and Cedar Creek a few miles south. Stonewall Jackson made it his base for the Valley Campaign of 1862. Robert Milroy held it through the winter of 1862-1863 until Richard Ewell took it back during the Gettysburg Campaign. Philip Sheridan finally broke Confederate control in September 1864 at the Third Battle of Winchester and held the town until February 1865. Confederate surgeon Hunter McGuire - Stonewall Jackson's personal physician - worked in Winchester's military hospitals and later helped draft the foundations of the Geneva Conventions on medical treatment in war. The town was a Confederate medical center after both Sharpsburg in 1862 and Gettysburg in 1863. At least 1,400 soldiers who died in Winchester hospitals are buried at Mt. Hebron Cemetery. Future presidents William McKinley and Rutherford B. Hayes both fought there. So did the grandfather of George S. Patton.

The Hessian prisoners of war held at Winchester during the Revolution used to walk to the high ridge north of town to buy apple pies from the Quaker farmers, and the ridge has been called Apple Pie Ridge ever since. The orchards stuck. The Shenandoah Apple Blossom Festival has run every spring since 1924, holding a parade, fireworks, and the coronation of an Apple Blossom Queen on the first weekend in May. Local schools and businesses close on Festival Friday. In a less obvious twentieth-century chapter, Capitol Records opened its East Coast Pressing Plant in Winchester in 1969. The plant pressed Talking Heads's Remain in Light, Yoko Ono's Fly, the Dead Boys' Young, Loud and Snotty, and thousands of other LPs before it closed in 1988. Born in Winchester in 1932, Virginia Patterson Hensley grew up to become Patsy Cline, the country singer who recorded Crazy and Walkin' After Midnight before her death in a 1963 plane crash. She is buried at Shenandoah Memorial Park just outside the city. Admiral Richard E. Byrd, the polar explorer, was also born in Winchester.

From the air Winchester reads as a compact city of about 28,000 people sitting at the natural gap where Interstate 81 and four U.S. routes converge in the lower Shenandoah Valley. The historic district is small and dense, with the 1828 Christ Church spire, the brick mass of the Robert Mills-designed Frederick Parish church, and the stone of Abram's Delight all visible within a few blocks. The pedestrian Loudoun Street mall runs three blocks through the downtown. North of the city, the Mt. Hebron Cemetery and the Winchester National Cemetery sit adjacent to each other, separated only by a stone wall, holding Union and Confederate dead from the seven battles. Apple Pie Ridge runs along the western horizon. The Blue Ridge rises about ten miles east; the Allegheny Front about fifteen miles west. The Shenandoah Valley opens south from the city like a long green tongue. Winchester is the smallest of the Virginia independent cities, but it has held its position at the valley's mouth for nearly three hundred years.