Road Trip Into Virginia's Piedmont

In which I drive deep into the heart of American history, from Washington, D.C., into Virginia’s Piedmont.

The rolling foothills of Virginia’s Blue Ridge mountains are some of the most consequential acreage in American history, birthing presidents (four of them), nurturing democracy, housing the capital of the Confederacy, and surviving the ravages of the Civil War. All this occurring in a landscape so bucolic locals routinely call it “God’s country.” And conveniently located within a few hours’ drive from the nation’s capital. This 320-mile loop starts in Washington, D.C., and hits Middleburg, Charlottesville, and Richmond. You can drive it in just over six hours, but y’all are in the South, honey, so take it slow and give it seven days. Any time of year works, but spring and fall bring special treats: the District’s famous cherry blossoms (a gift from Japan) in April, and turning leaves and apple harvests in the fall.

(A version of this article was first published in the September 2018 issue of Preferred Travel magazine.)

Day 1-2: Washington DC 

Check in to the stately Jefferson, a 1923 Beaux-Arts former apartment building turned luxury hotel, situated on 16th Street, a half-mile from the White House. A 2009 top-to-bottom renovation transformed it into one of the city’s most sought-after hotel addresses. The hotel’s interior evokes a Parisian elegance favored by the hotel’s namesake, founding father Thomas Jefferson.

D.C. in a day requires making tough choices. If you haven’t been, the monuments and Smithsonian museums of the Mall are a given, and free. The tidy townhome neighborhoods of Georgetown, Capitol Hill, or Dupont Circle make for perfect strolling and shopping. Not your first visit? Check out the latest: the Smithsonian’s eye-opening National Museum of African American History and Culture; the District Wharf, which has transformed the formerly dingy waterfront into a newly minted magnet for strollers, diners, and shoppers

As for dinner? It’s a delicious conundrum; the District garnered its own Michelin guide, only the fourth American city to do so, cementing its foodie status. There are 13 starred restaurants, from the Jefferson’s own Plume, to hometown hero José Andrés’s Minibar. Or, pick up some D.C. street cred and order a classic chili half-smoke at the counter at the original Ben’s Chili Bowl at 12th and U Streets.

Before departing the Jefferson, tuck into the library filled with books printed in the late 1700s and early 1800s; read the framed letters in the lobby, signed by Jefferson; and note the parquet floor at the Quill bar (you’ll see it again later).

Day 2-3: Middleburg

Suburban sprawl characterizes the first 30 miles of the drive west of Washington (though leave before noon to avoid the worst traffic). But thanks to the persistence of preservationists, fields, forests, and farms appear, against the backdrop of the Blue Ridge Mountains in all their purple majesty. You’ve entered a 180-mile long, 75-mile wide congressionally designated National Heritage Area known as the Journey Through Hallowed Ground

Middleburg is just one of 57 historic towns and villages in the historic swath that ranges from Gettysburg, Pennsylvania to Charlottesville, Virginia, but it is the toniest. The indubitable capital of the horse-and-hound set, it could just as well be in the English countryside as in Virginia’s. The always busy Middleburg Tack Exchange sells flasks and hunting horns, and in the quaint three-block downtown, jodhpurs are as common as yoga pants. It was Jackie Kennedy who put this place on the map in the early ’60s, escaping here with the kids for riding weekends when JFK was president. In the late ’70s, Elizabeth Taylor lived on a cattle farm here with her seventh husband, former Virginia senator John Warner. The Red Fox Inn, the oldest building in town, has received them all, and George Washington, too (in 1748 when the president-to-be was a young surveyor); duck in for a Virginia Gentleman bourbon on the rocks. Prefer vino? Wineries dot the area, including Boxwood and Greenhill Vineyards

Just outside town, the Salamander Resort’s 340 green acres beckon, with rooms facing the lawn or the hills, a sumptuous spa, and an “Equispective” program in which horses teach humans to communicate better with each other. One of the town’s best restaurants, Harrimans Virginia Piedmont Grill, is here; try the fried local chicken with buttermilk biscuits and honey sourced from the estate’s beehives.

Day 3-5: Charlottesville

Don’t program the GPS toward Charlottesville just yet. It’s less direct, but you won’t regret taking Skyline Drive, a scenic two-lane byway in Shenandoah National Park, with hiking paths (keep an eye out for white-tailed deer, wild turkey, and black bear) and numerous scenic outlooks to the Blue Ridge Mountains, the Shenandoah Valley, and the Piedmont. Skyline Drive ends in Waynesboro and it’s a short 20 miles to Charlottesville, home of Thomas Jefferson.

The country’s third president may not have literally built the town, but he conceptualized and designed its most famous landmarks, the University of Virginia and Monticello, his marvelous and quirky estate outside of town—together a UNESCO World Heritage Site. Stroll the Lawn at Jefferson’s vision for an “academical village,” lined with student rooms and classrooms and dominated at one end by a grand Rotunda housing a library. Walk to The Corner, the hub of student social life and grab a pizza slice at the Mellow Mushroom or a beer at the Virginian. For pricier fare, head to the Downtown Mall, where options include the C&O Restaurant and Alley Light.

Jefferson the brilliant but flawed genius is best understood at Monticello, where you can tour the house filled with inventions such as an ingenious copying machine and a revolving bookstand; check out the parquet floor of the parlor (it should look familiar if you were paying attention at the Jefferson Hotel back in D.C.). Visit the gardens where the Renaissance man experimented with figs from France and peppers from Mexico. Most important, learn about the enslaved people who worked the estate; at the African-American graveyard at Monticello, ponder the paradox of the slave-owning writer of the words, “All men are created equal.”  

You’re in the neighborhood, so pop into another presidential home—Highland, the more modest farm of fifth president James Monroe. From there, it’s a 20-minute drive to Keswick Hall, a lavish estate and golf resort formerly owned by Sir Bernard Ashley, the widower of designer Laura Ashley. The hotel reopens in 2019 after an extensive renovation, though the stunning Pete Dye golf course remains open.

Virginia is for Lovers, goes the state tagline, but in these parts, it is definitely for wine lovers. Thomas Jefferson was the first to recognize the potential of the terroir, and today more than 30 wineries produce some of the best bottles in the East Coast, including Jefferson Winery (on land Jefferson’s Italian winemaker partner owned) and Blenheim (founded by musician and native son Dave Matthews).

Day 5-6: Richmond

It’s a straight shot to the capital of Virginia and the former capital of the Confederacy. Here, Patrick Henry uttered his famous revolutionary cry, “Give me liberty or give me death!” Steeped in centuries of sometimes controversial history, the River City has nevertheless managed to balance its reverence of the past with a hip and modern sensibility. 

Your headquarters is the The Jefferson, opened in 1895, the unapologetically opulent grande dame of Richmond hotels in the heart of downtown, with its gilded and glass-domed lobby (with marble pools that once held live alligators). Rooms are spacious and reminiscent of a downtown pied-à-terre (there’s even a doorbell outside each room).

Richmond is one of the darlings of the New South, a quirky mix of hipster and history. Its food scene sources from the regional bounty and injects creative flair into southern food ways. Thanks to a new batch of aquaculture farmers, the Chesapeake oyster has made a comeback, and there’s no better place to get it than Richmond (try Rappahannock Restaurant). Oh, and to wash it down, there’s a hopping brewery, distillery, and cidery scene (try Ardent Craft Ales).

There’s more than enough to do within the 60-ish square miles of the city. Explore the restored warehouses and taverns of Shockoe Slip, check out the medley of architecture in the Fan District, go vintage shopping in Carytown, raft the rapids of the James River. Whatever you do, don’t miss the White House and Museum of the Confederacy, part of the American Civil War Museum. Christy Coleman, its female, African-American director, is breaking down barriers and ensuring stories are told from a variety of perspectives. 

Day 6-7: DC

Back in the city, check into the Watergate. Yes, that Watergate. The hotel, part of a complex whose name became the definition of scandal underwent an overhaul by Israeli architect Ron Arad and reopened after a nine-year hiatus in 2016 with a mid-century mod vibe full of gleaming curves, colorful swoops, and a sly nod to its past notoriety (room key tags read “No Need to Break In”). There’s a whiskey bar and a cigar room and all the niceties, but on a clear day the place to be is the roof deck with views of the shimmering city and the Potomac River. 

DC has a thriving arts scene, and you’re just a short walk from the Kennedy Center, its premier performing arts center. Didn’t score tickets to mega-hit Hamilton (it runs through mid-September)?  Line up for same-day tickets to whatever else is playing, or catch a free performance every evening at 6pm at the Millennium Stage. Afterwards, take a walk along the river in the other direction to the venerable Georgetown neighborhood, with its tidy 19th-century row houses. Dine at celebrity haunt Café Milano, or for a fancier feast, try a tasting menu at the stalwart 1789.

This is a city that loves a boozy brunch on the weekends, so don’t dare depart without partaking of the tradition, perhaps at Café Leopold or Blue Duck Tavern in the West End. And whether it’s spring or not, pick up some of DC’s famous cherry blossoms for the folks back home. Stop by Georgetown Cupcake to pick up a six-pack of their pink confections.


A version of this article was first published in the September 2018 issue of Preferred Travel magazine. Landscape photo by Byron Johnson on Unsplash.