The Loneliest Road


Northern Virginia’s largest city, Winchester (pop. 28,108) 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, $10) near downtown. She’s buried in Shenandoah Memorial Park, a mile (1.6 km) southeast of town.


Located at the heart of northern Virginia’s “Hunt Country,” where senators, ambassadors, and aristocrats mix at multimillion-dollar country estates, Middleburg (pop. 841) is a small but immaculate town with a four-block business district packed with antiques shops, art galleries, and real estate agencies.

Many of Middleburg’s brick- and stone-fronted buildings date from colonial times, including the Red Fox Inn and Tavern (2 E. Washington St., 540/687-6301 or 800/223-1728, $189 and up), on US-50 at the center of town. Originally built in 1728 as a coach inn and tavern, it’s now a comfortable and upscale B&B and restaurant. There are a couple of other good places to eat, including the Upper Crust Bakery (4 N. Pendleton St., 540/687-5666), a local favorite offering cookies and sandwiches among the usual array of baked goods.

East of Middleburg, US-50 winds through gently rolling farmlands for a dozen mi (19.3 km) before hitting the outlying suburbs of Washington DC.

Map of the Loneliest Road through Virginia.
Map of the Loneliest Road through Virginia.

Related Travel Guides