Winchester History

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Chronological 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 quiz

Inside Historical Winchester Quiz

Winchester, VA is full of such rich history that is passed by without recognition everyday. Through a weekly game, 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.


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 for more information about Charley Rouss.


 

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.

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.


More Winchester history coming soon:

  • Celebrities & Public Figures
  • Judge John Handley
  • French & Indian War/George Washington
  • Revolutionary War/Daniel Morgan
  • Civil War/Stonewall Jackson
  • Industrial Heritage
  • Old Town Winchester