Northern Virginia’s largest city, Winchester (pop. 26,203) is a surprisingly quiet and pleasant small city, best known for the extensive apple orchards that fill the surrounding countryside. 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 Loudoun Street, between Piccadilly (US-50) and Cork Streets, 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 in 1963 at age 30. Cline, whose greatest hits include “Crazy,” “Sweet Dreams,” and “Walkin’ after Midnight,” lived in Winchester from ages 3 to 16 in what’s now the Patsy Cline Historic House (608 S. Kent St., 540/662-5555, $8) near downtown. She’s buried in Shenandoah Memorial Park, a mile southeast of town.