Middleburg & Aldie

Hunt country. The stretch of Route 50 from Aldie through Middleburg pairs Loudoun’s most polished tasting rooms with its deepest horse-and-hound heritage. Boxwood Estate brings architect-designed, appointment-style Bordeaux precision; Greenhill pours estate wines at a 1762 manor; Chrysalis grows the world’s largest planting of Virginia’s native Norton grape; and Cana and 50 West stack Bull Run Mountain views behind their vines. Quattro Goomba’s wine-and-brewery compound and Lost Barrel’s horse-farm brewery keep things casual, and Mt. Defiance in Middleburg proper distills rum and pours cider a block from the town’s boutiques. Base here if your ideal day mixes tastings with a landmark-inn dinner — Middleburg’s restaurant row is the best in the county.