Northern Virginia’s largest city, Winchester (pop. 24,750) is a surprisingly quiet and very pleasant small city, best known for the extensive apple orchards that fill the surrounding countryside, producing some 250 million pounds of fruit each year. The I-81 freeway, complete with the usual sprawl of shopping malls and fast-food franchises, cuts across US-50 along the east side of Winchester, but the downtown district is eminently strollable, especially the pedestrianized Old Town area around Loudon Street, between Piccadilly (US-50) and Cork Street, where you can visit George Washington’s office or Stonewall Jackson’s Civil War headquarters.
After apples and American history, Winchester is probably most famous as the hometown of Patsy Cline, the inimitable country singer who died in a plane crash on March 5, 1963, at age 30. Cline, whose greatest hits include “Crazy,” “Sweet Dreams,” and “Walking After Midnight,” lived in Winchester from age 3 to age 16 in a small house at 608 S. Kent Street near downtown, and dropped out of high school to earn money making milk shakes at Gaunt’s Drug Store, south of downtown at Loudon Street and Valley Avenue. She’s buried in Shenandoah Memorial Park, a mile southeast of town.
Other sites associated with Patsy Cline are included in the handy brochure “Celebrating Patsy,” available inside the Kurtz Cultural Center (daily; free; 540/722-6367), in Old Town Winchester at 2 N. Cameron Street, which also has extensive displays on local and Civil War–era history and culture.
US-50 crosses our Appalachian Trail route near 1,100-foot-high Ashby Gap,
15 miles east of Winchester.
