Middleburg Hunt Country & Virginia Wine

Middleburg was platted in 1787 by Levin Powell on land purchased from Joseph Chinn (a cousin of George Washington's). The 18-block grid survives largely intact with stone and brick commercial buildings from the 1800s. The National Sporting Library & Museum, opened in 2007, houses over 20,000 volumes on equestrian and field sports in a purpose-built facility — one of the finest specialized sport libraries in the world. The Pink Box patisserie on Federal Street is the essential first stop.

The Red Fox Inn has operated continuously since 1728 — one of the oldest inns in continuous operation in America. The tavern room with its stone floors and low beams served Civil War soldiers, Kennedy-era fox hunters, and Jacqueline Kennedy (who kept horses at nearby Glen Ora estate 1961–1963 and made the Red Fox her regular dining room). The kitchen serves Virginia countryside cooking: game, roasted meats, Chesapeake seafood, and a wine list weighted toward Virginia producers.

A 28-acre Middleburg estate planted to Bordeaux varieties by Rachel and John Kent Cooke (son of Washington Redskins owner Jack Kent Cooke) in 2005. The winemaking consultant is Stéphane Derenoncourt of St-Emilion, and the Bordeaux Blend and Rosé consistently earn scores above other Virginia producers. The tasting room in a converted stone outbuilding has mountain views across the hunt country.

The upscale dining room at the Salamander Resort in Middleburg — one of the finest country house hotel restaurants in the mid-Atlantic. The menu draws from the resort's own garden and from a network of Northern Virginia and Shenandoah Valley producers; the game, the Virginia trout, and the seasonal root vegetable preparations are standouts. The bar stocks the complete lineup of local distilleries.