Guides

A group of six wines outdoors with award medals

Chiswell’s Best Year Ever at the 2026 Governor’s Cup Gala

March 17, 2026  |  Chiswell Farm & Winery

Category: News  |  Tags: Crozet, wine

The most prestigious wine competition in Virginia is, by far, the Governor’s Cup. With over 670 entrants from across the commonwealth, any Virginia winery is lucky to stand out among the crowd! Governor’s Cup medals are highly coveted by winemakers, and it’s at the Governor’s Cup Gala where the awards are officially given out.

This year’s Gala took place on Thursday, March 12, at Main Street Station in Richmond, VA. Chiswell was among the wineries who received gold medals in this year’s competition, and we were invited to pour our winning wines for our peers! Henry Chiles, the vineyard manager at Chiswell, was there to personally accept our medals and represent our family-owned winery.

In attendance: Lisa Henson, manager of Carter Mountain’s Wine Shop; Henry Chiles, Chiswell’s vineyard manager; and Kephany Powell, the tasting room manager at Chiswell.

Chiswell’s Governor’s Cup Medals

Six individual vintages from Chiswell Winery were honored in this year’s competition, which is more than in any prior year! Two gold medals and four silver medals came home with us for the following wines:

๐Ÿฅ‡ 2023 Meritage (new!)
๐Ÿฅ‡ 2023 Merlot (new!)
๐Ÿฅˆ 2021 Meritage
๐Ÿฅˆ 2022 Petit Verdot
๐Ÿฅˆ 2023 Petit Manseng (new!)
๐Ÿฅˆ 2024 Sauvignon Blanc (new!)

That’s four brand-new vintages for Chiswell, including a novel blend in our latest meritage. Our red wine blends are especially popular, with the 2021 Meritage winning for a third year in a row!

The Governor’s Cup Gala

The Virginia Wine Board throws a spectacular celebration each year with impeccable atmosphere and gourmet catering. The highlight for us is meeting other winemakers and enthusiasts during the walk-around tasting. We brought our 2023 Meritage and 2023 Merlot to show off, which were both hits. We’re grateful for the kind words we heard from folks who tried them!

Later in the evening, it was time to make the big announcements: which wines were in the Governor’s Case? Who had won the best-in-show awards?

This Year’s Governor’s Case featured:

  1. 7 Lady Vineyards, 2023 Meritage
  2. Barboursville Vineyards, 2024 Vermentino
  3. CrossKeys Vineyards, 2024 Cabernet Franc
  4. Fifty-Third Winery and Vineyard, 2023 Two Springs
  5. Glen Manor Vineyards, 2023 Vin Rouge
  6. Granite Heights Winery, 2024 Humility
  7. Michael Shaps Wineworks, 2023 Cabernet Franc
  8. Pollak Vineyards, 2023 Merlot Reserve
  9. Trump Winery, 2018 Blanc de Noir
  10. Valley Road Vineyards, 2023 Cabernet Franc Reserve
  11. The Winery at La Grange, 2024 Petit Manseng
  12. Woodbrook Farm Vineyard, 2024 Petit Manseng

And the overall Governor’s Cup Winner was Valley Road Vineyards, for their 2023 Cabernet Franc Reserve. Congratulations to our neighbors, just down the road in Afton! It’s a well-deserved win, and we’re thrilled one of our fellow Monticello Wine Trail wineries brought home the grand prize.

We’d also like to congratulate Blue Bee Cider for winning Cider of the Year with their 2024 Hewe’s Crab. Though we specialize in wine, we’re an apple-growing family too, and we love seeing excellent Virginia-made hard apple ciders getting proper recognition.

How the Judging Works

Months before the event, the Virginia Wine Board selects a group of respected wine experts to serve as the competition’s judges. A panel of six judges blind tastes each wine, ranking them on their appearance, aroma, flavor, overall quality, and commercial suitability. They then give wines a rating on a 100-point scale, mirroring the rating system used by Wine Enthusiast, Wine Spectator, and others.

Wines earn medals when their average scores meet a high threshold: 85 out of 100 for silver, and 90 out of 100 for gold. The 12 highest-scoring wines of the year are placed in the Governor’s Case (so only the top 1.8%!), and the highest-scoring wine wins the overall Governor’s Cup. Cider is judged separately, with a Cider of the Year also awarded at the Gala.

Go for the Gold! Try Our Governor’s Flight, Available Now

Experience the wines that impressed the judges this year with our Governor’s Flight, including two brand-new gold medal vintages! This flight presents our award winners in a curated tasting order that puts each of these phenomenal reds in the spotlight:

๐Ÿฅ‡ 2023 Meritage (new!)
๐Ÿฅ‡ 2023 Merlot (new!)
๐Ÿฅˆ 2021 Meritage
๐Ÿฅˆ 2022 Petit Verdot

A tasting flight of four red wines with hershey's kisses

The only reason we’re able to keep creating new and innovative vintages each year is because we have the support and trust of our guests. We owe a massive part of any awards we earn to you all, and we appreciate it! Make sure to come out to Chiswell soon and try this year’s winners for yourself.