Virginia Wine Country
280 miles round-trip from D.C.
East of the Blue Ridge Mountains, the Piedmont region of Virginia still has the same rolling hills and fields that captivated Thomas Jefferson and James Monroe—only now it lures the likes of locals John Grisham and Robert Duvall. Country lanes wind through villages of trim clapboard structures and around pastures framed by white fences. Recently, progressive farms and serious wineries have blossomed, but life continues at a blissfully slow pace.
Lay of the Land
JFK and Jackie may have put Middleburg in the national spotlight when they chose it for their weekend escape from D.C., but it’s long been loved by the horsey set for its polished, hunt-country style. Dignified estates, where the paddocks and barns are as well kept as the houses, ring the compact, low-key downtown. Tucked away from busy Route 211, tiny Washington (69 miles from Washington, D.C.) still occupies the same five-block by two-block grid laid out by the first president himself. The neat-as-a-pin brick municipal buildings would seem out of a period movie if the town weren’t so vibrant. The Inn at Little Washington draws a well-heeled crowd that has helped turn the community into an impressive hotbed of culture, with two theaters and a clutch of excellent galleries. In the past two decades, the Main Street of Culpeper has gone from run-down Americana relic to lively commercial hub. On the town’s southern outskirts, Chuck Miller turns corn into Virginia Lightning, using an old family recipe and one of the state’s only legal moonshine stills. Moseying speed is best for sampling the area’s small burgs. On a stroll through Madison, on rural Route 231, you’ll find an old wooden church converted into a quilt shop, a diner where high school teams gather postgame to wolf down fried cheesecake, and front porches meant for lingering. Charlottesville may be best known as home to the University of Virginia, but much of the action revolves around the pedestrian mall, where a free-speech monument—a massive slate wedge with chalk for passersby to scrawl their thoughts—was just unveiled in front of City Hall. Our founding fathers would be proud.
Washington, D.C. to Middleburg: 42 miles
Middleburg to Washington, Va.: 43 miles
Washington, Va. to Charlottesville: 58 miles