Hunt Country

Middleburg, Virginia: A Fall Weekend in the Heart of Hunt Country

Along the country roads leading from Washington, D.C., rolling pastures and prancing horses beckon travelers to stay awhile, indulging in the equine traditions and hospitality of a small town in Virginia.

Autumn rolls into Loudoun County, Virginia, weaving a tapestry of gold and russet leaves in the trees as a crisp breeze whistles over rolling green hills tucked at the base of the Blue Ridge Mountains. The rhythm of cantering horse hooves thunders in the fields, a familiar refrain in this part of the country, just more than an hour’s drive west of the capital. Though barely 800 souls call Middleburg home, the town’s reputation is well regarded as the Nation’s Horse and Hunt Capital.

Written by Lydia McMullen · Photography by Caroline Jean Gray and Marcy Black Simpson

Riders in collared coats follow a pack of American foxhounds down a country lane beneath blazing autumn trees — The Middleburg Hunt traces its origins to 1905. Each September, forty American foxhounds lead riders in collared coats through the countryside north and east of town.

The arrival of fall heralds Middleburg’s most anticipated equestrian traditions. The Middleburg Hunt and the Virginia Fall Races draw spectators from near and far to witness the time-honored events woven intricately into the region’s heritage. At the latter, the oldest continuously operating racecourse in Virginia dating to 1911, crowds gather at Glenwood Park, dressed in tailored tweed jackets, polished leather boots, and silk scarves, embracing the pageantry that accompanies the excitement of the sport.

Two riders in hunt attire canter across a green field

While the Thoroughbreds blazing across the track are easily the most eye-catching display—from polo to flat and harness racing to steeplechase—the culture of equestrianism in Middleburg is just as enticing. Blankets are spread across the grass, and Champagne is sipped beneath upscale tailgating tents throughout the affair.

A white barn and silo in morning fog behind a pasture fence

The town itself is the perfect setting for such dignified occasions. Rambling stone walls, like those found in the English countryside, and bucolic farmland lead the way to streets lined with antiques shops and local eateries.

The Red Fox Inn & Tavern

Throughout the twentieth century, Middleburg played host to a star-studded guest list, perhaps most notably Jacqueline Kennedy Onassis and Elizabeth Taylor. At The Red Fox Inn & Tavern, one of the oldest continually running inns in the United States, these former patrons sipped cocktails and settled within the comfortable accommodations. John F. Kennedy even once held a press conference in the property’s upper tavern.

Welcoming travelers since 1727, The Red Fox Inn has been extending Virginia hospitality since long before America became a nation. That legacy lives on especially in the Dining Room, where four-course dinners featuring juicy cuts of steak and Virginia wines invite guests to indulge in evening meals steeped in history.

Eggs Benedict, breakfast potatoes, tea, and orange juice on a plaid tablecloth

The Middleburg Hunt

A long-standing Virginia tradition, the Middleburg Hunt traces its origins to 1905, when two gentlemen set out to settle a rivalry between their English and American foxhound packs. The first week of each September, the hunt returns in full pageantry as forty American foxhounds lead riders in collared coats and brass buttons emblazoned with initials “MH.” Spanning a region of ten to fifteen miles in the countryside north and east of Middleburg, the hunt is a much-anticipated affair for locals and travelers.

A rider and hounds cross a misty autumn field

Shopping the Historic District

Along the main thoroughfare of the historic district, local retailers such as Tully Rector and Country Classics offer stylish clothing options when selecting an outfit for the races, while Crème de la Crème and Every Little Something brim with gifts to take home. Antiques stores and tack shops stand side by side, and nearby wineries invite visitors to linger over glasses of locally produced vintages.

Storefront of Crème de la Crème on Middleburg’s main street

Tweed hacking jacket and floral blouse displayed on mannequins in a Middleburg shop

Gilt convex mirrors, an eagle sconce, and a silver tea service in a Middleburg antiques shop

Within the embrace of Virginia’s Hunt Country, a devotion to all things equestrian sets the tone, and fall obliges, painting a colorful backdrop for a season of sport, tradition, and camaraderie that has defined Middleburg for generations.