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Four Chiswell wines with four Governor's Cup medals.

Chiswell Wins Four Medals in the 2025 Virginia Governor’s Cup

March 19, 2025  |  Chiswell Farm & Winery

Category: News

The logo of the Virginia Governor's Cup.

Each year the Virginia Wineries Association hosts the most prestigious wine competition in Virginia, the Governor’s Cup, in partnership with the Virginia Wine Board and the Virginia Vineyards Association. This year, we were honored to have received four awards for different Chiswell vintages, including two gold medals, their highest award given to wines the judges deem of “outstanding quality.”

This year, our medal recipients were:

🥇 2021 Cabernet Sauvignon

🥇 2022 Cabernet Franc

🥈 2021 Chardonnay

🥈 2021 Meritage

Our winning wines were featured at this year’s Governor’s Cup Gala, hosted in Richmond on Thursday, March 13. We had a phenomenal time at the Gala, sharing our medalists with other enthusiasts while sampling the absolute best of Virginia wine. There were so many fascinating flavors, techniques, and personalities on display throughout the evening! Our hats go off to the wonderful winners (both wine and cider!) we had the chance to experience.

Q&A with Henry Chiles, Vineyard Manager

Here’s what our lead grower, Henry Chiles, had to say after the event:

Henry Chiles with VA Governor Ralph Northam.
Virginia Governor Glenn Youngkin with Chiswell Vineyard Manager Henry Chiles.

Chiswell only just opened for business in 2021. How does it feel to already have multiple vintages rank as among the best in Virginia?

A: It feels great! We’re so blessed to live in a region capable of producing world-class wines. It also doesn’t hurt that we’ve had some really exceptional vintages the last few years, including ‘21, ‘23, and ‘24.

Why do you think these wines in particular stood out to the judges?

A: For the cabernet franc, I think it was the ability of the wine to embody the aspects of the vineyard and the soil. As the vineyard manager I get a full backstage view of all the factors that go into producing our fruit. This wine was able to highlight the differences between this site (Chiswell) and our other cab franc growing sites.

The cabernet sauvignon stood out for its superb drinkability, in my opinion. It’s not as heavily oaked as some California cab sauvs, and this in combination with our clay soils creates a uniquely Virginian cabernet sauvignon that I think anyone could enjoy.

Virginia wine has absolutely made a name for itself on the world stage at this point. What is it like being a part of the Virginia wine community? What does the future look like for the industry?

A: It’s such a pleasure being a part of the Virginia wine community. The collaborative nature of the Virginia wine community is what strengthens and unites us as an up-and-coming wine region on the world stage. I think our wines are continuously improving year over year as both our winemakers and vineyard managers adopt new strategies to best fit the Virginia climate.

Do you have a personal favorite Chiswell vintage?

A: My personal favorite is the 2021 Chiswell Sauvignon Blanc; unfortunately, I only have a few bottles left! My favorite of what we’ve got in the tasting room right now is the 2021 Cabernet Sauvignon for a red wine and the 2021 Petit Manseng for a white.

Is there anything growing now you’re excited about? Any hints about future Chiswell varietals?

A: We planted a few new blocks of both red and white varietals in the spring of 2022 that we’re anticipating getting our first harvest from this year! I won’t spill the beans quite yet on what they are, but I can promise that at least one will be new to Chiswell. I’m also greatly anticipating the bottling of some fantastic reds from the 2023 vintage that are still aging in barrel. I think these could be the very best wines we’ve produced yet!


It was an honor to have our wines celebrated in this year’s Governor’s Cup, but as Henry said, the best is yet to come for Chiswell. We hope you take the opportunity to come out and try our award-winning vintages—our new Governor’s Flight is the perfect chance to try all four 2025 medal winners in a curated tasting order!

As for future wines, stay in the loop by subscribing to our monthly newsletter, and follow us on Facebook and Instagram to get updates on Chiswell goings-on. We’re grateful for the support of our loyal guests; we couldn’t have achieved this without you!

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