Winchester History


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 ( The area is replete with historical sites and visitor attractions.

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.”


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.

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