Start at: Downtown Leesburg
Begin with a stroll along the town’s brick sidewalks. The Loudoun Museum (16 Loudoun St., SW; 703-777-7427; admission $3) can fill you in on Leesburg’s interesting history. For example, it changed hands about 150 times during the Civil War. Wandering is okay, too—from the corner of King and Market streets, head in any direction to check out the old stone houses and shops. Before leaving, pop into Puccio’s New York Deli (211 Loudoun St., SE; 703-779-7676) for picnic sandwiches. The Balboa is a favorite, and its spicy fillings of prosciutto, capicola, salami, and provolone are easily paired with a rustic red wine.
Next stop: Stone Tower Winery
This winery is a jaw-dropper, big enough to have two tasting rooms. The Harvest Barn—a good choice for families or visitors with pets—features six tasting bars, a clubby lounge area, and a vast green lawn for your picnic (tables and chairs available, or bring a blanket). The Tower View tasting room, for ages 21 and up, includes a large bar and a marketplace with snacks and gifts (no outside food allowed). At either, try the Hogback Mountain Bordeaux-style blend. Tasting: $15.
Last stop: Zephaniah Farm Vineyard
Just two miles but worlds away is Zephaniah. In the parlor and library of the multigeneration manor house, you’re likely to find the owners, Bill Hatch and Bonnie Archer, known for their friendly, seated tastings. Curious guests get filled in on the wine, the house, and the history of the farm, where Angus cattle and sheep are raised alongside grapes. Try the Cabernet Franc, which is the first grape the family planted, in 2002. Tasting: $10.
Round trip from DC: 89 miles
Read more from our winery guide:
This article appears in the May 2017 issue of Washingtonian.