Winchester History

At one time a Shawnee Indian camping ground, Winchester was founded in 1744 by Colonel James Wood and is the oldest city in the Commonwealth west of the Blue Ridge Mountains. Below is a condensed chronological history of Winchester compiled by the City's Planning Director, Tim Youmans.

Additional information about the history of Winchester can be found at the Winchester-Frederick County Historical Society website.


Town of Winchester founded by Col. James Wood on land granted to Thomas, Lord Fairfax.


George Washington makes his first trip to Winchester at age 16 as a Land Surveyor.


Town of Winchester chartered by the Virginia General Assembly.


Abram's Delight built- oldest known remaining house in the City is now a house museum.


Fort Loudoun erected in City under guidance of George Washington during French & Indian War.


Geo. Washington first elected to public office as local rep. to Virginia House of Burgesses. At his death in 1799, Washington would be attended by three physicians, one of whom was Dr. Craig from Winchester.


Daniel Morgan leads riflemen on famous bee-line Revolutionary War march to Boston.


Central water system installed in Winchester- one of the earliest public water systems in US.


Public Market House/Town Offices built- early rules for sanitary meat, produce sales & handling.


Agricultural Society of the Valley organized- Winchester area serves as major wheat producer.


Medical School of the Valley of Virginia founded- produces the first graduating class in Virginia.


Valley Turnpike macadamized- private toll road Company opens Valley for economic prosperity


Winchester and Potomac Railroad completed- opens faster market route to Baltimore ports


Frederick County Courthouse built- excellent Greek Revival structure, now a Civil War museum


Mt. Hebron cemetery organized- early community cemetery. Chateauesque Gatehouse built in 1902


Trial of John Brown presided over by Judge Richard Parker from Winchester. Cadaver of John Brown’s son Owen was brought to Winchester by med school students. Ironically, the first casualty of Brown’s raid on Harper’s Ferry Arsenal is depot manager, Heywood Shepherd, a free black man from Winchester.


Civil War- Winchester changes hands approx. 70 times between Union & Confederate occupation. A number of Winchester women function as spies for the north and south. Mary Greenhow Lee and Cornelia Peake McDonald keep detailed diaries of troop movements sympathetic to the Confederate cause. Rebecca Wright, a Quaker working with African-American Slave Thomas Law, provide critical information about Confederate forces to the Union Army days before the decisive Third Winchester Battle that would represent the last occupation of the Confederacy in Winchester.


First Battle of Kernstown (March 23)- Gen. Thomas ‘Stonewall’ Jackson’s only battle loss, but was a strategic victory for the Confederacy because it diverted Union reinforcements from Peninsula Campaign along the eastern shore of Virginia. Jackson’s personal physician, Dr. Hunter Holmes McGuire of Winchester later would amputate Jackson’s arm and attend to him until his death later that year. McGuire was credited with originating the custom of immediately releasing medical officers upon their capture during war. This would later be incorporated into the Geneva Convention.


First Battle of Winchester (May 25)- Jackson’s Army soundly defeats Union forces in Winchester.


Second Battle of Winchester (June 13-15)- Confederate victory was a prelude to Gettysburg.


Second Battle of Kernstown (July 24) – Union Army badly defeated by Gen. Jubal Early. The First and Second battles of Kernstown were on approximately the same ground. The City of Winchester and County of Frederick assisted the local non-profit Kernstown Battlefield Association to acquire most of the core battlefield site straddling the City-County line in the late 1990’s.


Battle of Cedar Creek (Oct 19)- just south of Winchester. Major Union victory seals Lincoln’s reelection and leads to Gen. Sheridan’s burning of the Shenandoah Valley.


Stonewall (Confederate) Cemetery dedicated within boundary of Mt. Hebron Cemetery.


National (Union) Cemetery dedicated- a “stone’s throw” away from confederate cemetery.


Town of Winchester becomes City of Winchester, independent of the surrounding County


John Kerr School opens- first “modern” public school named for local childless cabinet-maker John Kerr, whose will provides for funding education of poor children of Winchester.


Judge John Handley's bequest- Pennsylvania Judge loves “southern City” and bequeaths funding for Handley High School, Handley Library, School for Black Students, and ongoing private endowment for Winchester public schools. City school children still march to his grave at Mt. Hebron to honor him in May of every year.


Rouss City Hall built- Charles Broadway Rouss, who goes pennies-to-riches with NYC dept store chain contributes half the funding of City Hall. Rouss also donates Rouss Fire Hall, public water works, and Mt. Hebron Cemetery fencing in City among other projects. All benefactor of Rouss Hall at University of Virginia.


Winchester Memorial Hospital opens- moves to suburban campus in 1990 and becomes one of seven largest medical centers in Virginia. Now represents largest employer in the region.


Handley Library opens - considered finest example of Beaux-Art structure in Virginia.


Willa Cather, local County resident, wins the Pulitzer Prize for her book ‘One of Ours.’


Handley High School opens- architecture inspired by Jefferson’s Univ of Va. Grounds in front of the school designed by nationally renowned Olmstead Brothers including elements incorporated into Frederick Law Olmstead’s plan for Central Park in New York City. School basement served as a secret vault for the Corcoran Art Gallery in Washington, D.C. and housed over $1 Million worth of art treasures during WWII.


Spottswood (Spotsy) Poles, born in 1886 in Winchester, retired from a notable professional baseball career in the Negro Leagues. He was known as the "Black Ty Cobb" given his speed, batting average, and bases stolen.


First Shenandoah Apple Blossom Festival- grand marshal’s have included: Bob Hope, Lucille Ball, Bing Crosby, Robert Wagner, Hal Linden, and Dan Akroyd. Sport’s Marshal’s have included Hank Aaron, Willie Mays, Sugar Ray Robinson, Tony Dorsett, and Joe Theismann.


Local native Harry F. Byrd, Sr. elected governor of Virginia. Famous as a conservative “pay-as-you-go” democrat. Goes on to become U.S. Senator. Winchester resident Harry Byrd, Jr. follows in father’s footsteps. Byrd “Machine” considered one of the strongest ever in US state government.


Douglas School opens for African-American children of Winchester to replace overcrowded facility in Old Stone Presbyterian Church. The school is named in honor of abolitionist Frederick Douglass. All City schools were integrated in 1966 at which time it became an intermediate school. Today it is known as the Douglas Learning Center.


Admiral Richard E. Byrd's first Antarctic mission.


Winchester-Frederick County Historical Society formed- refurbishes oldest house and operates 3 museums in historic structures: Abrams Delight; Stonewall Jackson HQ; and Geo Washington Office.


John Kirby, famed Black Jazz musician raised in Winchester, performed with Chick Webb and Fletcher Henderson Bands in New York City. Went on to become a famed recording artist on Columbia, Decca, and RCA Victor labels including performances with Benny Goodman.


German POW's housed in City during WW II. Work to help local industry while U.S. servicemen overseas.


Last regularly scheduled passenger rail serving Winchester ends with final B&O rail service to Baltimore.


Shenandoah College (now University) relocates to Winchester – City businessmen convince small music conservatory to move and build new campus. Aggressive growth leads to prominent university offering undergraduate and graduate business School, extensive health profession studies, arts, and general studies for over 2400 students today.


Preservation of Historic Winchester (PHW) founded- grassroots nonprofit spearheads preservation of numerous properties in Old Town. Promotes establishment of Historic District established in 1967.


Interstate 81 is completed along the eastern boundary of Winchester leading to the creation of multiple industrial parks and the expansion of industry in the area including Rubbermaid Products.


Winchester annexes nearly 6 square miles of Frederick County enlarging former 3.4 square mile City one year after City/County consolidation referendum passes in City, but fails in Frederick County.


Patsy Cline (b. 1932) elected to the Country Music Hall of Fame- local soda fountain waitress sings her way to Nashville and on to international fame even after tragic plane crash in 1963. Married on steps of home in downtown Winchester (now a public museum). Buried just outside Winchester.


Loudoun Street pedestrian mall is created when two blocks of Loudoun Street are closed to vehicles two years after City constructs first parking garage and implements Special Tax Assessment Districts.


Winchester National Register Historic District is established covering a 45-block area downtown.


Joint Judicial Center dedicated- Winchester City and neighboring County of Frederick consolidate court facilities in new downtown building 14 years after contentious annexation. Spirit of cooperation is further strengthened in mid-1990’s with agreements that keep County offices in downtown Winchester. Numerous other joint projects are undertaken between the two local governments in subsequent years.


Museum of the Shenandoah Valley, design by internationally acclaimed architect Michael Graves, opens to the public on the grounds of Glen Burnie (the ancestral home of Winchester founder James Wood).


One-way portions of Cameron and Braddock Streets converted to two-way traffic downtown.


Loudoun Street Mall renovated and splash pad, public restroom and arches at entry ways added.

(Based upon chronology prepared by Rebecca Ebert at the Handley Archives)

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