Winchester History
Once 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.
1744
Town of Winchester founded by Col. James Wood on land granted to Thomas, Lord Fairfax.
1748
George Washington makes his first trip to Winchester at age 16 as a Land Surveyor.
1752
Town of Winchester chartered by the Virginia General Assembly.
1754
Abram's Delight built- oldest known remaining house in the City is now a house museum.
1756
Fort Loudoun erected in City under guidance of George Washington during French & Indian War.
1758
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.
1775
Daniel Morgan leads riflemen on famous bee-line Revolutionary War march to Boston.
1808
Central water system installed in Winchester- one of the earliest public water systems in US.
1821
Public Market House/Town Offices built- early rules for sanitary meat, produce sales & handling.
1823
Agricultural Society of the Valley organized- Winchester area serves as major wheat producer.
1826
Medical School of the Valley of Virginia founded- produces the first graduating class in Virginia.
1836
Valley Turnpike macadamized- private toll road Company opens Valley for economic prosperity
1837
Winchester and Potomac Railroad completed- opens faster market route to Baltimore ports
1840
Frederick County Courthouse built- excellent Greek Revival structure, now a Civil War museum
1843
Mt. Hebron cemetery organized- early community cemetery. Chateauesque Gatehouse built in 1902
1859
Trial of John Brown presided over by Judge Richard Parker from Winchester. Also, the 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.
1862-1864
Civil War- Winchester changes hands approx. 70 times between Union & Confederate occupation.
1862
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.
1862
First Battle of Winchester (May 25)- Jackson’s Army soundly defeats Union forces in Winchester.
1863
Second Battle of Winchester (June 13-15)- Confederate victory was a prelude to Gettysburg.
1864
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.
1864
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.
1866
Stonewall (Confederate) Cemetery dedicated within boundary of Mt. Hebron Cemetery.
1866
National (Union) Cemetery dedicated- a “stone’s throw” away from confederate cemetery.
1874
Town of Winchester becomes City of Winchester, independent of the surrounding County
1884
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.
1895
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.
1900
Rouss City Hall built- Native Charles Broadway Rouss, who goes pennies-to-riches with NYC dept store chain contributes half the funding of City Hall. Turns blind and too sick to see building completed. Rouss also donates Rouss Fire Hall & public water works in City and Rouss Hall at Univ. of Va.
1903
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.
1913
Handley Library opens- considered finest example of Beaux-Art structure in Virginia
1923
Willa Cather, local County resident, wins the Pulitzer Prize
1923
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.
1924
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.
1925
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.
1929
Admiral Richard E. Byrd's first Antarctic mission. Credited with first flight to North Pole also.
1930
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.
1944
German POW's housed in City during WW II. Work to help local industry while U.S. servicemen overseas.
1960
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.
1964
Preservation of Historic Winchester (PHW) founded- grassroots nonprofit spearheads preservation of numerous properties in Old Town. Promotes establishment of Historic District established in 1967.
1973
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. Buried just outside Winchester.
1984
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 joint projects undertaken between the two local governments.
1991
Kurtz Cultural Center opens- historic structure saved from wrecking ball in 1988 becomes home to a variety of community functions over the years including PHW, Chamber of Commerce, and Old Town Development Board.
(Based upon chronology prepared by Rebecca Ebert at the Handley Archives and available at the Winchester-Frederick County Economic Development Website)











