LONELIEST ROAD
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Follow the
LONELIEST ROAD through:

MIDDLEBURG

Located at the heart of northern Virginia’s “Hunt Country,” where senators, ambassadors, and aristocrats mix at multi-million-dollar country estates, Middleburg (pop. 632) is a small but immaculate town with a four-block business district packed with antique 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 ($150–175; 540/687-6301 or 800/223-1728), at 2 E. Washington Street, 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’s a couple of other good places to eat, including the zesty Italian cooking at the Backstreet Cafe (540/687-3122) at 4 E. Federal Street; and the Upper Crust Bakery (540/687-5666) at 2 N. Pendleton Street, 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 miles before hitting the outlying suburbs of Washington, D.C.

US-50: Winchester to Washington D.C. map

US-50 Route Detail: Winchester to Washington D.C.

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