1606History
French Jesuit expeditions may have first entered the valley as early as 1606, as the explorer Samuel de Champlain made a crude map of the area in 1632.
1670Military
The first confirmed exploration of the northern valley was by the explorer John Lederer, who viewed the region from the current Fauquier and Warren County line on August 26, 1670.
1671Infrastructure
The explorers Batts and Fallam in 1671 reported the Shawnee were contesting with the Iroquoians for control of the valley and were losing.
1705Government
In 1705, the Swiss explorer Louise Michel and in 1716 Governor Alexander Spotswood did more extensive mapping and surveying.
1729History
=== 18th century ===
By the time Anglo-European settlers arrived in the Shenandoah Valley around 1729, the Shawnee were the principal occupants in the area of the Shenandoah Val...
1732History
The first German settler appears to have been Jost Hite in 1732, who brought ten other families, including some Scots-Irish.
1735History
A legal fight erupted in 1735 when Thomas Fairfax, Sixth Lord Fairfax came to Virginia to claim his land grant.
1736Architecture
By 1736, Scots-Irish built the Opequon Presbyterian Church in Kernstown.
1737History
He contracted for his own home Glen Burnie homstead around 1737, and it may have been used for early government business.
1738History
By 1738, these settlements became known as Frederick Town.
1743History
The County Court held its first session on November 11, 1743, where James Wood served until 1760.
1744History
Wood laid out 26 half-acre (2,000 m2) lots in 1744.
1748Architecture
Lord Fairfax, understanding that possession is 9/10ths of the law, built a home here (in present-day Clarke County) in 1748.
1751Architecture
The Ridge Road built before 1751 leading north from town was renamed Apple Pie Ridge Road.
1752Government
In February 1752, the Virginia House of Burgesses granted the fourth city charter in Virginia to 'Winchester' as Frederick Town was renamed after Colonel Wood's birthplace in En...
1753Military
In 1753, on the eve of the French and Indian War (Seven Years' War), messengers came to the Shawnee from tribes further west, inviting them to leave the Valley and cross the All...
1754History
The father of Shawnee chief Cornstalk had his own court at Shawnee Springs, near today's Cross Junction, Virginia, until 1754.
1755Civil Rights
General Edward Braddock's expeditionary march to Fort Duquesne crossed through this area in 1755 on the way to Fort Cumberland.
1756Military
In 1756, on land granted by James Wood, Colonel George Washington designed and began constructing Fort Loudoun, which ultimately covered 0.955 acres (3,860 m2) in present-day do...
1758History
In 1758 Wood added 158 lots to the west side of town.
1759History
In 1759 Thomas Lord Fairfax contributed 173 more lots to the south and east.
1763Military
Following the war, from 1763 to 1774 Daniel Morgan served in Captain Ashby's company and defended Virginia against Pontiac's Rebellion and Shawnee Indians in the Ohio valley (th...
1775Civil Rights
He led the 96 men of "Morgan's Sharpshooters" from Winchester on July 14, 1775, and marched to Boston in 21 days.
1797History
House of Representatives (1797–1799).
1861History
"Stonewall" Jackson's defense of the Shenandoah Valley in 1861, Jackson's Valley Campaign of 1862, the Gettysburg campaign of 1863, and the Valley Campaigns of 1864.
1862Military
Winchester served as a major center for Confederate medical operations, particularly after the Battle of Sharpsburg in 1862 and the Battle of Gettysburg in 1863.
1870History
This period lasted until January 26, 1870.
1917Infrastructure
In 1917 the Winchester and Western Railroad connected Winchester with Rock Enon Springs, moving both vacationers and supplies to the resort that is now Camp Rock Enon with far g...
1924Culture
== Arts and culture ==
=== Historic sites ===
=== Shenandoah Apple Blossom Festival ===
Winchester is the location of the annual Shenandoah Apple Blossom Festival, which has...
1968Economy
Capitol Records Distribution Corporation announced in 1968 the purchasing of land in Winchester, Va for a new record processing plant.
1969Economy
In 1969 Capitol Records' Pressing Plant in Scranton began phasing out its vinyl manufacturing in favor of the new Winchester plant.
1982Architecture
Apple Blossom Mall opened in 1982.
1983Economy
In 1983, a tire dump in the area containing over seven million tires burned for nine months, polluting nearby areas with lead and arsenic.
2005Culture
These apples were created in 2005 by occupants of the city and were placed at a specific location at the artists' request after being auctioned off.
2006Infrastructure
While the council began as a 13-member board, it transitioned from 13 to 9, beginning in 2006 and ending in 2008.
2008Infrastructure
However, in 2008 the city swung strongly into the Democratic column to support Barack Obama.
2012History
Even though Obama lost ground in 2012 and only carried the city by 148 votes, it has nevertheless stayed Democratic-leaning ever since.
2013History
The street was repaved with brick and landscaped in 2013.
2016Infrastructure
According to the City's 2016 Comprehensive Annual Financial Report, the top employers in the city are:
=== Record manufacturing ===
Winchester was home to Capitol Records' Eas...
2020History
As of the 2020 census, 100.0% of residents lived in urban areas, while 0.0% lived in rural areas.