With a history dating back to the first Quaker settlers arriving around 1729, historic Downtown Winchester provides more than 40 block of history. Also called Old Town, the narrow cobblestone roads and colonial architecture lead past elegant boutiques and cafes. The pedestrian mall along Loudoun Street provides charming sidewalk cafes and shops in a beautiful setting. Downtown Winchester is very walkable and the destinations are plentiful.

Fort Loudoun Historic Site served as George Washington's headquarters during the French and Indian War, George Washington's Office Museum dates back to 1755, and Stonewall Jackson's Headquarters Museum was used by the general during the winter of 1861. Other historic landmarks include the Patsy Cline Historic House, the Francis Barton Event Center, the Museum of the Shenandoah Valley, and the Shenandoah Valley Civil War Museum.

Living in Downtown Winchester isn't just about the history.