Beautiful inns and upper-crust events in Virginia’s horse country.

Horse Racing in Middleburg
Credit: © Liz Callar

Middleburg, which originally got its name because it was the middle point between Washington, D.C. and trading post Winchester, Virginia, is now a chic country enclave, known for its purposefully preppy residents and see-and-be-seen events such as fox hunts and horse races.

Market Salamander

Part café and part gourmet food shop, Market Salamander is a collaboration between owner Sheila Johnson and D.C. chef Todd Gray. The dining area is designed to resemble an outdoor courtyard, with stone flooring, a high ceiling painted with clouds, and a faux storefront hung with chalkboard menus. During warmer months, a real outdoor patio provides additional seating. The shop sells everything from artisan cheeses to homemade dressings, while the café serves locally inspired American fare, such as macaroni and cheese, crab cake sandwiches, and freshly baked blueberry-lemon cupcakes. Upstairs, the Wine Loft sells small-batch vintages from around the world.

Ashby Inn & Restaurant

Located at the foot of the Blue Ridge Mountains just an hour west of D.C., the 1829 Ashby Inn is home to an acclaimed New American restaurant serving lunch, dinner, and Sunday brunch. The restaurant contains four individually designed dining rooms, including one lined with local landscapes and another furnished with rustic wooden beams and booths. Relying on local farms for fresh seasonal ingredients, chef Tarver King creates “snacks” such as beignets with smoked crème fraîche and entrées like pork shoulder with whipped grits, chestnuts, and Honeycrisp apples. Innkeeper and sommelier Neal Wavra provides carefully chosen wine pairings.

Red Fox Inn

The Red Fox Inn evokes the charm of colonial Virginia with its 1728 stone building and period furnishings. Originally established as a tavern, the inn hosted such former guests as George Washington, General Jeb Stuart, John F. Kennedy, and Elizabeth Taylor. Housed in several buildings and cottages, the 15 guest rooms are individually designed, although many include working fireplaces, four-poster beds with lace canopies, and hardwood floors topped with traditional hooked rugs. The candlelit tavern serves regional fare such as peanut soup and fried chicken, while an on-site gallery showcases animal and sporting art.

Goodstone Inn & Estate

Formerly an 18th-century plantation, this 265-acre estate is now home to a luxury inn surrounded by dairy pastures and winding creeks. The 18 guest rooms are spread out among several tree-shaded cottages, as well as a converted carriage house, a bull barn, and a Colonial-style manor house. The cottages are individually designed, although many contain gas fireplaces, whirlpool tubs, and full kitchens stocked with homemade cookies. Some also have furnished porches with views of the distant Blue Ridge Mountains. In addition to a celebrated French restaurant, the grounds include a full-service spa, an outdoor pool, and scenic hiking trails.

Middleburg Spring Races

A horseracing tradition for almost a century, this annual steeplechase event takes place during the third weekend in April at the Glenwood Park Racecourse. First held in 1911, the event is now comprised of six different races, including the Temple Gwathmey hurdle contest, which draws some of the best competitors in the nation. Designed by renowned horse trainer Paul Fout and local architect Tommy Beach, the track itself includes New Zealand—style steeplechase fences, as well as huge logs, water features, and yew fences. A number of private boxes and tents are available for rent.

The French Hound

Inspired by his time spent in southern Provence, chef John-Gustin Birkitt opened this authentic French bistro in a white, Federal-style building near downtown Middleburg. The interior resembles a Provençal farmhouse, with large windows, white-clothed tables set with light wood chairs, and marigold-hued walls hung with framed French posters. The small bar area is warmed by a fireplace during the winter, and an outdoor patio provides additional seating when the weather is pleasant. Complemented by an extensive international wine list, the menu includes options like oven-roasted escargot with pastis-herb butter, and steak frites with caramelized shallot sauce.