Middleburg, Virginia

Less than an hour's drive from the nation’s capital, past the gridlock of Beltway traffic, past a smattering of tract housing, office parks, and strip malls, lies the heart of Virginia horse country. Just when you least expect it, the landscape unfurls, and you feel as if you’ve been parachute-dropped into the middle of the English countryside, only these are the lush foothills of the Blue Ridge Mountains. The sight of rolling pastureland, clapboard farmhouses, and stone fences slows your pulse to a resting rate. “Relax,” reads a sign with a sleeping fox at the entrance to Middleburg, and so you do.

Everybody wants a piece of this thirty-seven-acre town’s brand of rustic chic. To prove it, there’s a waiting list for post-office boxes with a prestigious Middleburg address. That’s probably why most of the 650 official residents are fiercely protective of their land and the town’s history, which extends back to pre-Revolutionary days when a young George Washington spent the night at the Red Fox Inn, an establishment that still anchors the main street. Locals may have deep pockets, but they shun glitz and relish living in a place where you can walk into restaurants in breeches and riding boots. For these reasons, rumors that Middleburg is on the verge of becoming the next Greenwich, Connecticut, send them running for cover.

Even if you’re not the scion of an old Virginia family, a privacy-seeking Washington powerhouse, or the owner of a farm with its own name, it’s easy to derive pleasure from a weekend visit to Middleburg. The antiques shops, vineyards, and horse stables have year-round allure, but the headline events are the spring and fall races and the annual Christmas in Middleburg celebration, which kicks off with a hunt parade down Washington Street.

Where to Stay
Book a room at the Goodstone Inn, a former estate and dairy farm a few miles from historic downtown. The Middleburg Hunt proceeds directly through the grounds, and there are stables for guests’ horses. The carriage house, built in the early 1900s, is the hotel’s hub and has been refurbished in true Middleburg style (read: English and French country plus antique flourishes), as have the guest cottages that dot the 265-acre property. The carriage house’s one-room restaurant, Hilltoppers, with its heart-pine floors, Palladian windows overlooking the woods, and seasonal menu, is a destination in itself.

Down the road, in Upperville, one of the many hamlets along John S. Mosby Highway, a charming Irish family has infused the Blackthorne Inn, once owned by George Washington, with a Gaelic flair. There’s a casual pub as well as an upscale restaurant, which is packed in the evenings.

In contrast to these sprawling countryside getaways, the Red Fox Inn sits on prime in-town real estate. As with most places in Middleburg, history seeps from its thick fieldstone walls. Built in 1728 as an ordinary that served travel-weary colonialists, the inn was later expanded and used during the Civil War as General Jeb Stuart’s headquarters and as a hospital for Confederate soldiers—the pine bar in the taproom is made from an old field operating table. The establishment’s high-profile past also includes regular visits from Elizabeth Taylor (during her Senator John Warner years) and the Kennedys (JFK even held a press conference there). Helpful hints: Ask for a room in the Stray Fox cottage, which is separate from the main house, and don’t leave without trying a cup of the peanut soup, the inn’s signature dish.

What (Else) to Eat
Start your day with eggs and Virginia ham at the Coach Stop, a 1950s-era diner smack-dab in the center of town. You’ll find typical java-house fare at the underground Cuppa Giddy Up and warm panini at Mello Out, a quaint little dugout with outdoor tables. The place to go for dinner is the French Hound, for classic bistro dishes in a warm Provençal setting. Order the radishes with sea salt to start—elegant and bright—and the hanger steak melts in your mouth.

Despite this handful of reliable options, including the reportedly excellent Rail Stop down the road in the Plains, Middleburg is a bedroom community, and most residents stay hearthside for meals. This is where the Home Farm Store, a purveyor of humanely raised meats and organic produce, comes in handy.

Where to Shop
Despite its noncommercial feel, Middleburg has more than sixty retailers, and you’ll be hard-pressed to find a shop without an equestrian theme. Hounds, foxes, and horses are featured almost everywhere, from the local bookstore, Books and Crannies, to the mini-department store called Fun Shop. In addition to its French linens and colorful ceramic guinea hens, Crème de la Crème has a paperie room full of letterpress cards that could distract a shopper for hours. Tucked away in a small building at the corner of East Federal Street is a business called Haute, with a trove of gorgeous below-market-price fabrics and sumptuous textiles. Also, check out the venerable Hastening Antiques on Washington Street as well as the upstairs gallery at the Red Fox Inn, which specializes in English and American sporting art.

Though most tourists in Middleburg do not come to town seeking high fashion, there are several upscale boutiques, including Tully Rector and Clothes Minded. But the shops that speak directly to the old-fashioned sensibility of the town and its residents are Highcliffe Clothiers, which specializes in bespoke suits and men’s furnishings, and Nobel Nielson Shoes, which carries everything from gusseted boots to preppy Italian loafers. Finally, there is Journeymen, a shop that practices the nearly extinct art of leatherworking, a necessity in a place that revolves around saddles and boots.