Johnson, cofounder of Black Entertainment Television, is one of the new Middleburg landowners: business barons who've been making an impression by thinking big and differently. Another, Cisco Systems cofounder Sandy Lerner, a philanthropist with an interest in animal rights, caused a stir when she purchased Ayrshire Farm and denied local fox hunters the right to pass through her land. (She sharpened the barb by opening a roadhouse tavern named the Hunter's Head, where a mounted huntsman's bust—sporting a riding helmet—overlooks the bar.)
But both Johnson and Lerner seem to have settled into their communities, and each offered an olive branch to her neighbors in the form of an excellent provisions store in downtown Middleburg: Lerner's Home Farm Store sells heirloom vegetables and rare-breed meats raised on her land; Johnson's Market Salamander is a prepared-foods mecca run by lauded D.C. chef Todd Gray. Both places happen to be just a stone's throw from Linda Tripp's—yes, Ms. Lewinsky's confidante's—German Christmas shop and Wursthaus.
Nevertheless, our first 15 minutes here proved that Middleburg's hunt-country bona fides remain intact. Like ski bums and surfers, Middleburg's equestrians have their own argot for discussing the sport's ripest conditions. We woke up one misty, bleak morning after our dinner in Paris to find the crowd at the Coach Stop, a diner along Middleburg's Main Street, raving about the excellent "scenting" and "footing" (for dogs and horses, respectively).
We tucked into a breakfast of country ham with grits and red-eye gravy and lingered with In & Around Horse Country (a bimonthly paper) until the sun burned off the fog. On the town green, the church bazaar was in full swing, offering items such as used jodhpurs and horse tack at fire-sale prices. One of us picked up a fern-gray custom-tailored riding blazer, and the other found a broken-in horse blanket, which had CHISHOLM embroidered on the flank in script, to picnic on. Then we shopped for fried-chicken box lunches at Market Salamander before heading to the Gold Cup.
The race takes place on the third Saturday in October, several miles south of Middleburg on a vast, impossibly green rolling plain called the Great Meadow. We drove along narrow asphalt back roads through fields—some trimmed with fence posts painted a deep black-green, others with stone walls stretching straight as plumb lines along their road frontage. In the fields, hay bales spotted the landscape with painterly irregularity.
The Gold Cup is a tough ticket, and at $55 per car and up to $11,000 for a railside tent, can be an expensive one, too. Families, frat boys and their girls, and people traveling on a budget tend to reserve the cheaper territory at the narrow ends of the roughly oval course. But the prime viewing spot is from Members Hill, a sloping green in front of the homestretch, and the most coveted places on the hill are the tailgating spots alongside the fence, where drivers of vintage wood-paneled Wagoneers and late-model Land Cruisers alike back up, open their doors, and party.
The race itself is visually stunning and perfectly paced for the attention of the tailgaters. At the crack of the pistol, all eyes watch as horses and their jockeys bolt out of sight. As the horses round the course, you see in the distance the jockeys' pastel jerseys flashing back into view now and again. That far away, their pace appears leisurely, languid even, and the tailgaters in their Lilly Pulitzer and wide-brimmed hats can relax, sip their juleps, nibble tea sandwiches, and primp the floral centerpieces on the table (or on the roof of the Mercedes). Then, several minutes later, the volume of voices along the track fence rises, and the crowd pivots to behold the pack of horses come thundering down the straightaway to the final jump and the finish line.
Compared with the plumminess of Members Hill, the wine-country experiences in this area have a neighborly informality. At Chrysalis, a winery founded in 1997 with the mandate to make the Norton, Virginia's native grape, viable for wine production, visitors are encouraged to cook out on the iron grills on the property. When the server conducting our tasting uncorked the winery's Petit Manseng—in our view, the house's finest wine, a Sauternes-like elixir and a superb match for foie gras—she volunteered, "Y'all, my girlfriends and I call this our hot-tub wine."