Find Award-Winning Wine in Charlottesville

Charlottesville was named 2023's Wine Region of the Year by Wine Enthusiast, and now you can find the best of the best by tasting the gold medal winners of the Virginia Governor's Cup. The Virginia Governor’s Cup is the premiere wine competition within Virginia, with over 620 of the best Virginia wines, ciders, and meads submitted and sampled by world-class judges. The rating system is based on a 100-point scale, also used by Wine Spectator, Wine Advocate, Wine Enthusiast, and Wine & Spirits.

The judging is rigorous. All wines go through a preliminary round of blind tasting. Qualifying wines then move on to the final round where each is reviewed by twelve judges. A wine’s average score is used to determine its medal status. Judges comment on a wine’s appearance, aroma, flavor, overall quality, and commercial suitability.

The twelve top-scoring wines are honored with inclusion in the prestigious Governor’s Case. These wines represent the very best of the best Virginia wines. In 2026, these wines from the Monticello Wine Trail are in the Governor’s Case:

Valley Road Vineyards 2023 Cabernet Franc Reserve
Barboursville Vineyards 2024 Vermentino
Michael Shaps Wineworks
2023 Cabernet Franc
Pollak Vineyards 2023 Merlot Reserve
Trump Winery
2018 Blanc de Noir
Woodbrook Farm Vineyard
2024 Petit Manseng

The top wine is the recipient of the Governor's Cup. This year, Valley Road Vineyards received this top honor for their 2023 Cabernet Franc Reserve!

Gold medals were awarded to 224 wines from 113 Virginia wineries, cideries and meaderies after a series of rigorous blind tastings. Across the Monticello Wine Trail region, 30 producers earned 72 gold medals. Want to try these award-winning wines? We’ve divided the region into “neighborhoods” to help you organize your time and travels.

Here are some tips for getting around and making the most of your travels:

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