Start at: Hillsborough Vineyards
Route 9 takes you through the onetime mill town of Hillsboro, a picturesque clutch of stone houses clinging to a hillside. The fieldstone look continues as you enter Hillsborough Vineyards. Seated tastings in the French-country-style tasting room can be paired with European cheeses and charcuterie. Red wines here are unfiltered, a style that winemaker Kerem Baki uses to preserve flavor and aroma. Try the Bloodstone, a rustic red from the hard-to-find Fer Servadou grape. Tasting: $12.
Next stop: North Gate Vineyard
Three miles south, North Gate is a leader in being green. Solar energy powers the operation, and eco-friendly bamboo and reclaimed wood were used in the tasting-room construction and furnishings. (The owners are happy to give an eco-tour; call at least a week ahead to arrange.) Try the Meritage blend, a perennial medal winner, and the apple wine, which is just fun. Tasting: $8.
Lunch stop: Monk’s BBQ
For lunch, head to downtown Purcellville and a picnic table at Monk’s. Refresh your palate with one of the local craft beers on tap, then order up smoked meats that range from tender brisket to dry-rubbed ribs. Before leaving, grab Nilla Wafer–topped banana-pudding cups to go. 251 N. 21st St.; 540-751-9425.
Last stop: Barns at Hamilton Station
The rustic look is authentic: Tastings are held in a 106-year-old wood-and-stone barn, while the farm’s dairy history is evoked by what look like cows by the pond. (“Are they real?” is a game here.) Taste the wine lineup (the 2014 Cabernet Sauvignon snagged the top prize in Virginia for 2017), then pick one to pair with your pudding. Enjoy both beneath a bright-red umbrella on the deck. Tasting: $8.
Round trip from DC: 111 miles
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This article appears in the May 2017 issue of Washingtonian.