News Archives | Chiles Family Orchards

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

Posted by :Alex Griffith On : March 17, 2026

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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:

🥇 2023 Meritage (new!)
🥇 2023 Merlot (new!)
🥈 2021 Meritage
🥈 2022 Petit Verdot
🥈 2023 Petit Manseng (new!)
🥈 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!

A wine glass and a bottle of red wine with an award on it — **🥇 2023 Merlot**

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!

**Henry Chiles** posing with our two gold medalists, the 2023 Merlot and 2023 Meritage.

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:

7 Lady Vineyards, 2023 Meritage
Barboursville Vineyards, 2024 Vermentino
CrossKeys Vineyards, 2024 Cabernet Franc
Fifty-Third Winery and Vineyard, 2023 Two Springs
Glen Manor Vineyards, 2023 Vin Rouge
Granite Heights Winery, 2024 Humility
Michael Shaps Wineworks, 2023 Cabernet Franc
Pollak Vineyards, 2023 Merlot Reserve
Trump Winery, 2018 Blanc de Noir
Valley Road Vineyards, 2023 Cabernet Franc Reserve
The Winery at La Grange, 2024 Petit Manseng
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.

Virginia Governor Abigail Spanberger awarding the 2026 Governor’s Cup to **Valley Road Vineyards**.

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:

🥇 2023 Meritage (new!)
🥇 2023 Merlot (new!)
🥈 2021 Meritage
🥈 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.

Thank You for a Record-Setting 2025 Season!

Posted by :Alex Griffith On : December 22, 2025

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This has been an amazing year at Chiles. We had long and fruitful peach and apple seasons, plus berries, sunflowers, pumpkins, zinnias, and more! It was wonderful to see so many people come out for pick-your-own and take home gorgeous fresh-picked fruit. You know, our family picked an especially big peach this year…

Our seasonal menu debuted new and delicious meals and treats. Grabbing a turkey and apple sandwich or tomato-basil pizza was a perfect lunch to enjoy after picking or with live music! Speaking of live music, we jammed out to over 50 performances on our outdoor stage. A big thank you to all the musicians who made each weekend rock.

We were especially busy this fall, with plenty of new and returning harvest-time events. These included Fall into Fun, Pumpkinfest, Enchanted Orchard Days, our Holiday Tastings Weekend, and Celebrate Local on Small Business Saturday. Whether you had the chance to join us or not, expect even more fun and festive events in 2026!

A woman in a witch costume picking apples, with the text "Enchanted Orchard Days"

A designed image with multiple products and the text "Holiday Tastings at Chiles Peach Orchard"

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Henry and the Giant Peach

Henry Chiles holding the world's heaviest peach

Did you catch the big news? Chiles Peach Orchard now holds the Guinness World Record for the heaviest peach at 1 lb., 13 oz! Discovered one day in late peach season by fifth-generation farmer Henry Chiles, he says the record was as much a fluke of nature as anything else.

“We didn’t do much extra other than what we would normally take care of the peaches. We just had the right weather conditions this year for growing monster peaches.” –Henry Chiles

Finding the peach was only half the battle. Henry and his sister, Ally Whitmer (née Chiles), put in the legwork to verify and prove it to the Guinness people. Witnesses, community members, and specialists all chipped in for the weighing. During the wait, though, the peach did lose a few fractions of an ounce!

Since the peach was found and verified, there’s been local and international news coverage. With over 2,000 likes on our announcement post, we’ve loved the excitement and curiosity from visitors and community members. One of the top questions we get is, “so, what did it taste like?” Truthfully, we never ate it! The peach is in the freezer for now, and we’re looking into having a 3D replica made. Hopefully, we can show it off to folks for years to come!

See You in 2026!

Our final day of the season is on Tuesday, December 23. Expect Chiles Peach Orchard to fully reopen for the spring in late March. Be the first to know when we reopen by signing up for our newsletter, or following us on Facebook and Instagram.

We planted a few surprises this year, though — don’t be surprised if we end up blooming a little early!

a girl in a pumpkin field pulling a wagon of pumpkins — 📷 josiebookhout

An apple cider slushie in front of a wreath — 📷 josiebookhout

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

Posted by :Alex Griffith On : March 19, 2025

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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.

A speaker in front of a screen at the 2025 VA Governor's Cup Gala — The final ceremony, revealing the Governor’s Case wines and the Governor’s Cup winner.

Two women serving wine from the Chiswell table at the Governor's Cup Gala in Richmond — The final ceremony, revealing the Governor’s Case wines and the Governor’s Cup winner.

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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Welcome, Kephany!

Posted by :Ivy Group Developer On : April 19, 2023

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At Chiswell Farm & Winery, we’re not just cultivating our vineyard. We’re cultivating a community. So as we enter our second full year of welcoming guests, we’re excited to introduce our Winery & Tasting Room Manager, Kephany Powell. Since September 2022, Kephany has been serving up exceptional wine and experiences to match. She plays an important role in our close-knit community—and in the exciting new developments on the horizon.

Toward the Tasting Room

After Kephany moved to Central Virginia in 1998, she began meeting with friends and family at Crozet vineyards, sharing the pleasures of companionship, wine, and those distinctive Blue Ridge views. Along the way, she became fascinated with the history of wine and viticulture. She grew enamored with the way that wineries serve as unique places to gather and make memories.

She’d found herself in a wine region with an exciting mix of the old and the new. We have a history of grape cultivation stretching back to Thomas Jefferson, and we’re also one of the up-and-coming wine regions of the world!

Kephany’s interest increased until, one day, she made the jump from her career in retail sales and management to a new career in the local wine scene. She worked at Veritas Vineyard and Winery and Keswick Vineyards before coming to Chiswell, where she combines the skills of her former career with her passion for wineries.

Crafting the Chiswell Experience

As the Winery & Tasting Room Manager, Kephany specializes in the guest experience. Visitors should feel, she says, like guests being welcomed into a home.

One of the most unique parts of Chiswell’s hospitality, which she loves, is that its beautiful and historic Greenwood home is fully open. Guests can choose any room to enjoy wine and fellowship with one another. From the cozy sitting rooms to the Big Ash Bar, from the porch to the sloping lawn, the variety of spaces allows visitors to tailor the perfect experience for their visit.

Kephany also helps guests select their wine. Her first piece of advice is always simple: drink what you enjoy! Then she might ask about the circumstance. Are you looking to sip a glass by itself, or to pair it with a meal? What is the occasion? The answers to all of these can help shape her recommendation.

For herself, she looks for wines that don’t feel overpowered by any single attribute. She loves when all the elements, from tannins to sweetness, reach a balance. Since she adores all the Chiswell wines she serves, it’s hard to get her to pick out favorites. If you press her, though, she just might choose the 2021 Sauvignon Blanc or the 2021 Cabernet Franc!

“I love engaging with our visitors and having the opportunity to serve delicious wines with a true sense of hospitality. It’s fun meeting new people and treating them to the Chiswell experience, but it’s also so rewarding to recognize familiar faces that walk through the front door.”
-Kephany

Exciting Developments

There’s so much to look forward to at Chiswell, Kephany says. One project she’s especially proud of is Crown Club. Since fall of 2022, Crown Club has offered members the opportunity to connect with exquisite wine and a tight-knit community of fellow enthusiasts. She can’t wait to carry out more of the quarterly celebrations where members pick up their wines and enjoy shared activities at the winery and orchards.

The elegant home and gorgeous views at Chiswell have also been drawing a lot of interest as a venue for weddings and special events. In the not-too-distant future, those special celebrations will be an exciting addition to Chiswell’s slate of activities. Already, small groups can book rooms to reserve a beautiful, private setting for their get-togethers.

Finally, the return to warmer months will bring extended hours, live music on Fridays and Sundays, and lots of other events that Kephany loves preparing for and then seeing our guests enjoy.

“I want everyone to experience the delicious wines and special qualities that characterize Chiswell, so I look forward to pouring you a glass soon!”
-Kephany

When you do come in for your next visit, be sure to say hi to Kephany!

Aerial view of Chiswell and surrounding landscape

Want a deeper experience of Virginia wine? Join the (Crown) Club!

Carter Mountain Orchard Open Every Day

Posted by :Kristen Dagli On : March 26, 2021

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The sweet smell of spring is in the air! C’mon out to breathe it in and enjoy panoramic views of Charlottesville growing greener, we’re now open daily 10 AM–5 PM.

Cheers Are in Order

Keep a glass ready, we’re preparing to release our new Carter Mountain wine! We can’t wait to share the fruits of our labor with you later this year.

Display of Easter merchandise at Carter Mountain Orchard

Have an Eggcellent Easter

Hop up the mountain to snag some truly adorable bunnies, kid-friendly crafts, and spring fling cookie cutters from the Country Store.

We won’t be hosting an egg hunt this year, though we can’t wait to get back to it in 2022!

On the Horizon

The sun just loves showing off and we are here for it!

Thursday Evening Sunset Series kicks off on May 7, keep an eye out for the musical lineup and ticking info on our calendar and Facebook page.

Cider donut with mountain views in background at Carter Mountain Orchard

Wednesday is the New Friday

You can find us now at the Local Food Hub Wednesday Drive-Thru Market @ Seminole Square (instead of Friday).

We’re keeping our Ivy Road Pop-up through 2021 on Thursdays– Saturdays.

Carter Mountain Orchard's recipe for apple cider donut bread pudding

Satisfy Your Sweet Tooth

If you thought you loved our apple cider donuts before, wait until you try our cider donut bread pudding.

Grab it fresh from the Country Store or whip up a batch yourself with our recipe.

Bottle of Bold Rock Hard Cider seasonal watermelon on ice — Bold Rock Watermelon Cider blends the iconic summer refreshment of watermelon with deliciously crisp Blue Ridge apple juice.

Enjoy the View with a Seasonal Cider in Hand

The Bold Rock Tap Room at Carter Mountain Orchard has also kicked off their 2021 season. Soon you’ll be able to admire the budding peach blossoms while sipping on your favorite brew, whether it’s hard cider, seltzer, tea, or lemonade.

Get fresh orchard info, ready-picked for your inbox by subscribing to Carter Mountain Orchards today!

Apple Season Will Look a Little Different This Year

Posted by :Franziska Matiuk On : September 4, 2020

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For over 40 years, the Chiles Family, along with our amazing staff, have invited people from all over to visit our orchard each fall to pick their own apples. It’s a family tradition for us, and we know for many of you as well. Our 2020 fall season must be different due to the COVID-19 pandemic. We are committed to protecting our staff and our guests.

Beginning Friday, September 11, we invite you to enjoy our fresh, mountain-grown apples, famous apple cider donuts, jams and jellies, and the beautiful view and hospitality that we are known for—in a new way.

We know that many of you may decide that 2020 is the year you will skip your visit. We will miss you, and we understand. We’ll be here when you are ready.

Some might want to enjoy our scenic view (and some cider donuts) but aren’t comfortable getting out of your car. We get it. And we can make that happen with our Scenic Drive-Thru.

Some may want to pick up donuts and apples but not the “hassle” of driving up the mountain. Here are some other ways to get a taste of the orchard.

And for those who still want to have your traditional fall experience like you always have, complete with apple picking, we can accommodate you through our ticketed entry.

So, please read the options carefully—planning ahead will make for the best apple season experience!

Visit Carter Mountain Orchard

Visit Chiles Peach Orchard

Archives for :

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

Chiswell’s Governor’s Cup Medals

The Governor’s Cup Gala

How the Judging Works

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

Thank You for a Record-Setting 2025 Season!

Henry and the Giant Peach

See You in 2026!

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

Q&A with Henry Chiles, Vineyard Manager

Welcome, Kephany!

Toward the Tasting Room

Crafting the Chiswell Experience

Exciting Developments

Carter Mountain Orchard Open Every Day

Cheers Are in Order

Have an Eggcellent Easter

On the Horizon

Wednesday is the New Friday

Satisfy Your Sweet Tooth

Enjoy the View with a Seasonal Cider in Hand

Apple Season Will Look a Little Different This Year

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