Virginians have been fermenting the juice from the grape since the first permanent English settlement in Jamestown in 1607.

That makes it the oldest and most experienced wine producer in the States—and, for the record, one of the most productive, offering visitors hundreds of wineries to check out. Each one will proudly boast of what they do with the grape. And for good reason, many have won coveted international awards.

The best way to sample a few of their extraordinary wines—and at the same time have a memorable holiday—is to select a suitable central point and expand from there (as time permits). My three favourite communities for an overnight are Middleburg, Washington (Virginia) and Charlottesville.

Award-winning Wineries

In the horsey community of Middleburg (about 80 kilometres northwest of Washington, D.C.), there are seven local wineries. A favourite is John Kent Cooke’s historic landmark property, Boxwood Estate Winery. Under the guidance of prominent Bordeaux winemaker Stéphane Derenoncourt, the winery has produced award-winning wines for the past six years in the Bordeaux tradition (Médoc, Saint-Émilion and Rosé).Five varieties of vines certified by the French government (Cabernet Sauvignon, Cabernet Franc, Merlot, Petit Verdot and Malbec) are used to create these outstanding wines. boxwoodwinery.com

Washington is another special world, a charmingly restored 18th-century farm community (about 105 kilometres southwest of Washington, D.C.). For wine lovers, there are about 30 small, artisan wineries to visit in the nearby counties. What makes Washington unique and worthy of an overnight is the world-famous Inn at Little Washington, which Chef Patrick O’Connell has placed on the map with his fine wines and cuisine. visitrappahannockva.com      

Near the historic university town of Charlottesville (about 160 to 190 kilometres southwest of Washington, D.C.) two wineries stand above all the others in the area, The Trump and Barboursville wineries. Formerly known as the Kluge Estate Winery and Vineyard, The Trump Winery is today considered one of Virginia’s most prestigious. Established in 1999, it is tucked away comfortably on the edge of the picturesque Blue Ridge Mountains, near Thomas Jefferson’s Monticello Estate. In the past 10 years, the winery has consistently won awards, nationally and internationally for its Kluge SP Rosé, Kluge SP Blanc de Blanc, and its Kluge New World Red. trumpwinery.com

Barboursville is also a unique property with a charming 18th-century inn for guests to overnight. Not far from James Madison’s Montpelier estate (and Monticello), this historic property is considered one of the first estates in modern times to develop seriously European wine varietals, adapted to Virginia’s terroir. The winery’s pride is the Octagon, a blended wine selected from its finest barrels of superior vintage varietals. barboursvillewine.net

A few other wineries, worthy of note, include Keswick Vineyards, Afton Mountain Vineyards, Fox Meadow Winery and Cooper Vineyards.