City Escape: Winchester, Virginia

Located an hour and a half from Washington, D.C., the roads surrounding Winchester, VA, provide a superb chance to roar away from the capital’s bustle on two wheels. Around the city, you’ll find astounding rural beauty, American history, and marvelous local eateries in equal measure.

Before you hit the road—or after your ride—poke around Winchester’s many historical sites. In addition to the Museum of the Shenandoah Valley (see below), you’ll find George Washington’s preserved office, the city’s oldest home dating to 1754, the Shenandoah Valley Civil War Museum in the historical downtown, and multiple Civil War battlefields and cemeteries.

Once the ride gets underway, rural Virginia quickly surrounds you with expansive farmland, interspersed with small, green woods. Cows and horses graze on pastures and fields that cover the gently undulating terrain.

This route consists of a mix of two-lane main roads and narrow single-vehicle country lanes with no centerlines. You’ll pop off the bigger roads for sections that meander along the Shenandoah River for beautiful water views or disappear into the forests separating the region’s farms.