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 |
|---|---|---|---|---|---|---|---|
| 1 | Cana Vineyards and Winery of Middleburg | 1 | 2 | — | 6 | 29 | 38 |
| 2 | 50 West Vineyards | — | 3 | 1 | 6 | 16 | 26 |
| 3 | Carriage House Wineworks | — | 1 | 1 | 8 | 9 | 19 |
| 4 | Delaplane Cellars | — | 1 | — | 7 | 21 | 29 |
| 5 | Chrysalis Vineyards at The Ag District | — | — | 1 | 5 | 8 | 14 |
| 6 | The Wine Reserve at Waterford | — | — | — | 6 | 11 | 17 |
| 7 | Greenhill Vineyards | — | — | — | 5 | 23 | 28 |
| 8 | Barrel Oak Winery & Brewery | — | — | — | 3 | 22 | 25 |
| 9 | Philip Carter Winery | — | — | — | 3 | 10 | 13 |
| 10 | 8 Chains North Winery | — | — | — | 2 | 17 | 19 |
| 11 | Slater Run Vineyards | — | — | — | 1 | 12 | 13 |
| 12 | Boxwood Estate Winery | — | — | — | 1 | 7 | 8 |
| 13 | Blue Valley Vineyard and Winery | — | — | — | 1 | 1 | 2 |
| 14 | Bluemont Vineyard | — | — | — | 0 | 10 | 10 |
| 15 | Twin Oaks Tavern Winery | — | — | — | 0 | 3 | 3 |
| 16 | Aspen Dale Winery at the Barn | — | — | — | 0 | 2 | 2 |
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.