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Middleburg Virginia AVA

16 wineries · 266 Governor's Cup awards · 2018–2026
Designated a federal AVA in 2012, the Middleburg Virginia AVA covers a horse-country landscape of stone walls and rolling pastures across parts of Loudoun and Fauquier counties in Northern Virginia. The region is anchored by the historic village of Middleburg itself, with additional clusters of wineries around Upperville, Delaplane, Philomont, and The Plains. Because of its proximity to Washington DC — roughly an hour's drive — the AVA has developed a distinctly polished wine-tourism identity, with architecturally ambitious tasting rooms and robust events programs. Red Bordeaux-style blends dominate here, though Viognier and Chardonnay are increasingly central to the story. Worth noting: not every winery in Loudoun County sits inside the federal AVA boundary, which runs south of Purcellville and Hamilton.

Award Leaderboard

16 wineries in this AVA have earned awards at the Virginia Governor's Cup Competition (2018–2026). The ranking below uses Olympic-style medal counting: Governor's Cup wins first, then Case selections, Best in Show honors, Gold Medals, and total awards.

# Winery Cup Case BIS Gold Silver Total
1Cana Vineyards and Winery of Middleburg12—62938
250 West Vineyards—3161626
3Carriage House Wineworks—118919
4Delaplane Cellars—1—72129
5Chrysalis Vineyards at The Ag District——15814
6The Wine Reserve at Waterford———61117
7Greenhill Vineyards———52328
8Barrel Oak Winery & Brewery———32225
9Philip Carter Winery———31013
108 Chains North Winery———21719
11Slater Run Vineyards———11213
12Boxwood Estate Winery———178
13Blue Valley Vineyard and Winery———112
14Bluemont Vineyard———01010
15Twin Oaks Tavern Winery———033
16Aspen Dale Winery at the Barn———022

Sorted by prestige: Governor's Cup Winner > Case Winner > Best in Show > Gold Medal > Total awards. Click any winery to see their complete award history.

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