Winchester History

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Historical Highlights

Winchester, founded in 1744, is the oldest Virginia city west of the Blue Ridge Mountains. Located at the northern entrance of the Shenandoah Valley, the City encompasses 9.3 square miles and is the medical, industrial, commercial and agricultural center for the surrounding areas. The City has a population of approximately 28,000 residents.

Winchester is a community with a rich heritage and a dynamic future. It is the home of General Stonewall Jackson's Headquarters, occupied by General Jackson during the winter of 1861-62. George Washington's Office where he spent much of his time in Winchester from 1748 till 1758, and the home of the country singing legend Patsy Cline (celebratingpatsycline.org). The area is replete with historical sites and visitor attractions.

Click here for the list of Winchester's Historical Highlights.

History Coloring Book

Stories by Tim Y the History Guy

Listen to interesting stories about Winchester's history from City of Winchester Planning Director and local historian Tim Youmans. These stories were included in the City's bi-monthly Rouss Review Podcast during the Winchester 101 segment. Listen to the entire podcasts at www.winchesterva.gov/rouss-review


City-Owned Museums

The City owns four local history museums (open April-October):

  1. Abrams Delight (1340 South Pleasant Valley Road) - Winchester’s oldest home, built in 1754 by the Hollingsworth family, served as the area’s first Quaker meeting house.
  2. Hollingsworth Mill (1340 South Pleasant Valley Road) - Located next to the Abram’s Delight house, was built in 1833 by David Hollingsworth, the great-grandson of Abraham Hollingsworth, Frederick County’s first settler. A restored and furnished log cabin completes this historic site.
  3. Stonewall Jackson's Headquarters (415 N. Braddock Street) - This 1854 Hudson River Gothic Revival style house has been restored much as it was when Jackson used it as his headquarters. The house contains the largest collection of Jackson memorabilia and also personal objects from members of his staff. 
  4. George Washington's Office (32 W. Cork Street) - An 18th century log and stone building interpreting the early years of Washington’s life, through its exhibit “George Washington and the West.” Washington used this office while he was building Fort Loudoun in Winchester. 

Click here for a complete list of area historic attractions and museums.


history quiz

Inside Historical Winchester Quiz

Winchester, VA is full of such rich history that is passed by without recognition everyday. Through this short quiz, several of those spots will be featured, and hopefully, you’ll learn something and gain a greater appreciation for your city.

Click here for the quiz and answers.

Rouss City Hall

Rouss City Hall

Rouss City Hall was built in 1901 thanks to a generous donation by Charles Broadway Rouss. Learn more about the interesting history of City Hall which has served many different purposes, other than government offices, over the years.

Click here for details.


Historical Figures

Charles B. Rouss

Charles B. Rouss

​Rouss biographer A.V. McCracken wrote in 1896: “There are bands, baseball clubs and every sort of organization in old Winchester which bear the name of the New York merchant…The name Charles Broadway Rouss will go down to unborn generations of Winchesterians as a synonym of all that is charitable, good and benevolent.”

Click here to read more.

Spottswood Poles

Spottswood Poles

A Winchester native, Spottswood Poles was a decorated WWI veteran (Harlem Hell Fighters) and legend in the Negro League (baseball). 

Click here to read more

Daniel Morgan statue

Daniel Morgan

Morgan was involved in many phases of the Revolutionary War between 1775 and 1781. He was famous for leading a 600-mile Beeline March in 21-days from Winchester to Boston in 1775. He commanded the Frederick Militia nicknamed ‘Morgan’s Riflemen’, which included the esteemed contingent of German soldiers from Winchester known as the "Dutch Mess". From there, Morgan, then a Captain, would head to Quebec where he would be forced to surrender after taking over command from a wounded Col. Benedict Arnold. He was jailed until freed two years later in a prisoner exchange.

Click here to read more.

Women in Winchester History

From a country music legend to civil rights advocates to government leaders, Winchester is home to many history-making women.

Click here to read more.


Street Naming History

The streets in the Old Town area of the city were named by Colonel James Wood back when he, as Winchester’s first Clerk of the Court for Frederick County, created the original 30-lot plat for Winchester in 1744. Lord Fairfax also created many of the streets in Old Town in the late 1750s. Dr. Garland Quarles, in his book “The Streets of Winchester, VA, The Origin and Significance of Their Names” provides an explanation for what these original streets were named for.

Click here for an overview.


Industrial Heritage

There is a rich industrial heritage in Winchester. You may know something about the apple industry (the Winchester area was once touted as the "Apple Capital"), but you may not have a good knowledge of Winchester as an early exporter of wheat. Likewise, you may not realize how much early and mid-Twentieth Century industry was downtown in the form of textiles.

Click here to read more.


More Winchester history coming soon:

  • Winchester's Historical Figures: George Washington, Stonewall Jackson, Judge John Handley and more
  • Wars in Winchester: French & Indian, Revolutionary, Civil War
  • Old Town Winchester