Thomas Jefferson tried -- and failed - to grow grapes at Monticello. Fortunately, Virginia has had plenty of winemaking success since then.
The state has nine major wine regions, but Middleburg, located about an hour outside Washington, D.C., is a great place to start. The area is home to six wineries, not to mention a charming horse-and-hunt culture.
Where to sip: Begin at the 21-acre Boxwood Estate, the grand dame of Middleburg vineyards, open Friday to Sunday. For $10 you can taste Boxwood's four wines, including Topiary, a Decanter World Wine Award-winning Cab Franc and Merlot blend ($25 a bottle). An extra perk: Keep your glass as a souvenir.
This winery was designed by Jacobsen Architecture, a D.C.-based firm also known for Jacqueline Kennedy Onassis's home in Martha's Vineyard. Boxwood is one of the most elegant vineyards in the region, so don't miss the chance to explore. The circular cave, where wines age in a ring of French oak barrels, is especially striking.
At Chrysalis Vineyards, six miles away, you can sample wines made from native Norton grapes; the vineyard is the country's largest grower of this American varietal. The owners of the sprawling 412-acre property invite visitors to stick around after their tasting to drink in views of the Bull Run Mountains and use the Chrysalis outdoor grills. If you like, wash down your BYO burgers or shish kebabs with one of the winery's best value bottles, like the 2011 Mariposa rosé, $15.