Start at: Chrysalis Vineyards
Chrysalis was popular even before opening a new tasting room in 2015, with walls of windows and big wrap-around decks. Try the Norton, one of its stars. Beyond wine, estate-raised beef is often for sale, and on-site cheesemaking is planned. Tasting: $15.
Next stop: Cana Vineyards and Winery of Middleburg
A few miles down Route 50 is a grand-scale winery that can handle crowds. The adults-only upstairs includes a gazebo, large deck, and TV room. Downstairs are shaded patios and choice spots for picnicking by the vines, with live music every weekend. Try Le Mariage, Cana’s flagship wine, a Bordeaux-style blend anchored by Petit Verdot. Tasting: $10.
Rest stop: Middleburg
Stretch your legs with a walk in downtown Middleburg, the heart of horse country. The National Sporting Library & Museum (102 The Plains Rd.; 540-687-6542; admission $10) exhibits equestrian art, while Middleburg Tack Exchange (103 W. Federal St.; 540-687-6608) sells saddles and riding gear. Tastings of a different sort occur at Mt. Defiance Cidery & Distillery (207 W. Washington St.; 540-687-8100). Middleburg Common Grounds (114 W. Washington St.; 540-687-7065) is a casual spot with all-day breakfast and lunch, including half-smokes with jalapeño mustard and tuna with Tuscan white beans and olives.
Last stop: Greenhill Winery & Vineyards
End the day at one of the rare local vineyards to offer sparkling wine. You can enjoy a glass of Blanc de Blanc on the winery’s lawn, which looks out over forest and mountains. Tasting: $14.
Round trip from DC: 90 miles
Read more from our winery guide:
This article appears in the May 2017 issue of Washingtonian.