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Winchester is an independent city located in the extreme northwestern portion of the Commonwealth of Virginia in the USA. The city's population was 23,585 according to the 2000 U.S. Census. Winchester is the county seat of Frederick County and the principal city of the Winchester, Virginia-West Virginia Metropolitan Statistical Area, which is a part of the Washington-Baltimore-Northern Virginia, DC-MD-VA-WV Combined Statistical Area. The Bureau of Economic Analysis combines the city of Winchester with surrounding Frederick county for statistical purposes. Winchester is the home of Shenandoah University.

Around 1000 A.D. early native population included Cacapon, Opequon, Shawnee and Tuscarora tribes. By the Middle Ages, the natural north-south conduit of the Great Appalachian Valley made Winchester a likely place for tribal warfare as bands of Catawba, Cherokee, Delaware, Iroquois, and Shawnee marauded the valley plains for hunting grounds. The first tribe with real control of the valley were the Susquehannocks, who were then raided and expelled by Iroquois around 1600. Supposedly the Iroquois allowed the Shawnee tribe to either village or establish transient campsites here at Shawnee Springs from about 1694 to the mid-1700s, overlapping with the arrival of early Quaker settlers and homesteaders. The father of the historical Shawnee chief Cornstalk had his court here.


French Jesuit expeditions first entered the valley as early as 1606 resulting in a crude map drawn in 1632 by Samuel de Champlain, but the first confirmed exploration of the northern valley was by explorer John Lederer who viewed the valley from the current Fauquier and Warren County line on August 26, 1670. This was followed by more extensive exploration and mapping by Swiss explorer Louise Michel in 1705 and then Governor Alexander Spotswood in 1716.

In the late 1720s Governor William Gooch promoted settlement by issuing large land grants and, subsequently Robert "King" Carter", manager of the Lord Fairfax proprietorship, acquired 200,000 acres (800 km²). This combination of events directly precipitated an inrush of settlers from Pennsylvania and New York, made up of a blend of Quakers and various German and Scots-Irish homesteaders.


The settlement of Winchester began as early as 1729, when Quakers like Abraham Hollingsworth migrated up the Great Valley along the Indian Path (later known as the Great Wagon Road) from Pennsylvania and began to homestead on old Shawnee campgrounds. The first German settler appears to be Jost Hite in 1732, who brought ten other families including some Scots-Irish. Though an Anglican colony, Governor William Gooch had a tolerant policy on religion, and throughout Virginia, the availability of land grants brought in many religious families, who were often given 50-acre (200,000 m2) plots through the sponsorship of fellow religious grant purchasers and speculators. As a result, the Winchester area became home to some of the oldest Presbyterian, Quaker, Lutheran and Anglican churches in the valley. The first Lutheran worship was established by Rev. John Casper Stoever Jr., and Alexander Ross established Hopewell Meeting for the Quakers. By 1736, the Opequon Presbyterian Church in Kernstown was built. A legal fight erupted in 1735 when Thomas Fairfax, Sixth Lord Fairfax, came to Virginia to claim his land grant, which included "all the land in Virginia between the Rappahannock and the Potomac rivers", an old grant from King Charles II, and which overlapped and included Frederick county.


By 1738 these settlements became known as Frederick Town. The county of Frederick was then carved out of Orange County, and the first government was created consisting of a County Court as well as the Anglican Frederick Parish (for purposes of tax collection). Colonel James Wood, an immigrant from Winchester, England, was the first court clerk, laid out 26 half-acre (2,000 m²) lots around 1741, and constructed his own residence, Glen Burnie. Finally, the County Court held its first session in 11 November 1743, where James Wood served until 1760. Lord Fairfax, understanding that possession is 9/10ths of the law, built a home here (in present-day Clarke County) in 1748. By 1750 the Virginia House of Burgesses granted the fourth city charter in Virginia to Winchester as Frederick Town was now re-named after Colonel Wood's birthplace of the old Saxon capital of Wessex, and later of England, Winchester. In 1754, Abraham Hollingsworth built the local residence called Abram's Delight, which served as the first local Quaker Meeting house. George Washington spent a good portion of his young life in Winchester helping survey the Fairfax land grant for Thomas Fairfax, Sixth Lord Fairfax, as well as performing surveying work for Colonel Wood. In 1758 Colonel Wood added 158 lots to the west side of town, and then Thomas Fairfax contributed 173 more lots to the south and east.

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