Small-Town Escapes: Middleburg, VA

A well-heeled haven for horse lovers in the Northern Virginia hills

Photo: Lucy Brown

Population: 751
Drive Time: Sixty-five minutes west of Washington, D.C.

So appealing is an address in Middleburg, Virginia, the ne plus ultra of American equestrianism, that the town has 2,000 post office boxes and only 751 residents. Founded in 1787, three years before Washington, D.C., in the lush rolling country an hour west of the capital, it has retained both its natural beauty and its devotion to three things: horses, riders, and the animals they chase, foxes. In the six short storybook-like blocks of the main drag, Washington Street—composed of a lovely array of Federalist homes and tidy storefronts on shaded brick sidewalks with views

The inn's on-brand door knocker.

Photo: Alan Goldstein Photography

The inn’s on-brand door knocker.

of the distant Blue Ridge—there’s the Red Fox Inn, the Fox’s Den Tavern, and Foxfire Gallery & Antiques, with paintings of riders in red coats, called “pinks.” Foxcroft girls’ school outside of town allows students to bring their horses, just as the railway magnate Edward Harriman did a century ago when he came down from New York to found one of the oldest fox-hunting clubs in America; Orange County Hunt still rules Middleburg’s social roost.

The 24-Hour Agenda: Fortunately you don’t need to know a whelp from a whipper-in (the huntsman in charge of the pack) to appreciate Middleburg. Start at the handsome stone facade of Home Farm Store, a specialty food emporium, butcher shop, and purveyor of excellent breakfast pastries. If you feel the need to blend in, shop for a vintage “ratcatcher” (tweed jacket) at the Middleburg Tack Exchange over on Federal Street. Duck into the tasteful Sporting Gallery for moody oils depicting countryside much like that on the edge of town.


Whet the palate with the smooth applejack at the Mt. Defiance Cidery and Distillery, and impressive Bordeaux-style reds at nearby Boxwood Winery. Lunch on crab cakes at the Market Salamander and “cow puddle” cookies (butterscotch and molasses) from Upper Crust Bakery. Finish with a cappuccino at Cuppa Giddy Up.

Now you’re ready for the National Sporting Library and Museum, a unique collection of sculpture, paintings, etchings, and 26,000 books, including a beautiful volume containing Teddy Roosevelt’s defense of fox hunting. You can peruse paintings that beautifully represent the history of fly fishing and wing shooting, all housed in a lovely campus of restored brick and fieldstone buildings. They’re right next door to the offices of the weekly equestrian magazine The Chronicle of the Horse, naturally.

For an authentic Middleburg pub experience, visit the Red Horse. Regulars have the burger and fries; there’s beer on tap and good rail bourbon.

Meet the Locals: “Calvin Klein bought his chaps here,” says Punkin Lee, the owner of Journeymen Saddlers, the revered custom

Riders, horses, and hounds prepare for the chase.

Photo: Robb Scharetg

On the Hunt

Riders, horses, and hounds prepare for the chase.

leatherworking shop that outfits most everybody interested in anything related to riding hereabouts. Punkin was born in Middleburg but won’t say when, or what her first name is. “My father was ‘Peaches,’ the postmaster for twenty-six years, and nobody knew what his real name was, either.” She helped Jackie O. as well as Calvin, but generally keeps the town and environs up-stirrup. “It’s all about horses. The ripple effect keeps the community together.”

“A lot of things have happened here I can’t tell you about,” says Turner Reuter, referring to the very private Red Fox Inn, which he owns along with Red Fox Fine Art. (He also breeds hunting dogs and gives shooting lessons on the side.) Originally a coaching inn—lodging situated at a midway point along a prominent travel route—it was purportedly built in 1728. Today the Red Fox serves good American food, and the Night Fox Pub on the second floor is a nice place for a late nightcap. And considering that Tom Cruise, Paul Newman, Liz Taylor, and plenty of others have stayed here, you never know whom you’ll run into in the hallways.