20+ Charlottesville Area Wineries to Discover on the 2023 Virginia Governor’s Cup Gold Medal Trail

The Virginia Governor’s Cup is the premiere wine competition within Virginia. More than 100 wineries participated – that’s about a third of all Virginia wineries – and 614 wines were judged in 2023. 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. The top wine is the recipient of the Governor's Cup, and this year's winner is a local vineyard – and member of the Monticello Wine Trail – Delfosse Vineyards and Winery!

In addition, cideries throughout Virginia also compete in a special category of the Governor’s Cup. Albemarle CiderWorks was awarded 2023 Best in Show for its 2021 Orchard Blush and is the only cidery in Virginia to win this distinction.

The following wines from local vineyards are part of the 2023 Governor’s Case.

Barboursville Vineyards 2021 Vermentino Reserve
Delfosse Vineyards and Winery 2021 Screaming Hawk
Jefferson Vineyards 2019 Meritage
Jefferson Vineyards 2021 Petit Manseng
Pollak Vineyards 2017 Meritage
Trump Winery 2016 Blanc de Noir
Trump Winery 2019 New World Reserve

Gold medals were awarded to 142 wines from 66 Virginia wineries, cideries and meaderies after a series of rigorous blind tastings. Across the Monticello Wine Trail region, 21 producers earned 62 gold medals. Of these, 7 were selected for the Governor’s Case, representing 60% of the highest-ranked wines throughout the competition. Want to try them all? We’ve divided the region into “neighborhoods” to help you organize your time and travels.

For each winery, we’ve added a brief overview to pique your interest – however, this just scratches the surface of what each one offers! Visit their individual websites to learn more.

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

• The Virginia Governor’s Cup has a passport aps that tracks visits to wineries and earn rewards.
• Cville Hop-On Tours, Charlottesville Wish Wish Wine Tours, Crozet Trolley, and Monticello Wine Tour & Coach Co. provide excellent tours to area wineries. Look to our wine tours page for upscale transportation options. Local companies can help you develop a personalized itinerary, so all you have to do is just sit back and enjoy the ride!
• Looking for a unique experience? Indian Summer Guide Service leads horseback rides through local vineyards. Both C’ville Picnic and Shaniece Be Just Be Well Experience organize luxurious, sumptuous picnics.
• Consider staying overnight at a vineyard! Visit the winery lodging page for a list of wineries with lodging, and visit the Places to Stay page for a complete list of local accommodations.

Start your journey near “the mountaintop” where Filippo Mazzei first planted grapes for cultivation 250 years ago.

Cunningham Creek Winery: 2019 Rivanna Red

Family-owned and -operated, Cunningham Creek welcomes everyone - kids and pets included! Enjoy award-winning wines while watching your dog run off-leash in the dog park, or relax with a wine and a picnic. Light snacks are available for purchase in the tasting room, and be sure to check the event page for live music, food trucks, and trivia!

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, outdoors
Reservations Required: No
Maximum Group Size: Tasting reservations required for parties of 8+
Offers overnight accommodations: No

Eastwood Farm and Winery: Petit Manseng & 2021 Chardonnay

New to the Charlottesville winery scene, Eastwood opened in 2020, is woman-owned, and is already producing gold medal winning wines! Visiting their property offers options galore including multiple indoor and outdoor spaces to sip their delicious vintages (along with house-made craft beer and cider), plus hiking trails and an on-site food truck. You’ll want to stay all day!

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes
Reservations Required: No
Maximum Group Size: Contact for large parties
Offers overnight accommodations: Yes

Jefferson Vineyards: 2019 Meritage, 2021 Petit Manseng, 2019 Petit Verdot Reserve, 2019 Petit Verdot Reserve Upper Vineyard

Purveyors of fine Virginia wines for more than 40 years, Jefferson Vineyards is a Charlottesville area staple. Situated on the very same site where Thomas Jefferson and Filippo Mazzei began the first commercial vineyard in Virginia, an event pre-dating the Revolutionary War. Jefferson Vineyards has since bridged its traditions with modern viticulture practices to realize a dream nearly 250 years in the making.

They offer seating in two indoor tasting rooms in addition to their outdoor garden and patio, seasonally. No reservations are required; however, groups are limited to parties of 8 or less, and the suggested visit time is a maximum of 2 hours.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, outdoors and in small tasting room
Reservations Required: No
Maximum Group Size: 8
Offers overnight accommodations: Yes

Trump Winery: 2016 Blanc de Noir, 2016 Brut Reserve, 2017 Blanc de Blanc, 2019 New World Reserve & 2021 Sauvignon Blanc

Planted with 227 acres of French vinifera varieties, Trump Winery is not only Virginia’s largest vineyard, but also the largest vinifera vineyard on the East Coast. A breathtaking 1,300-acre estate with an incredible vantage point which overlooks the beautiful rolling hills of the Charlottesville, Virginia countryside. Enjoy wines by the bottle, glass, and flight or enhance your visit by making a table reservation and pairing your selected varietals with artisanal menu items.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes
Reservations Required: No
Maximum Group Size: 10
Offers overnight accommodations: Yes

A short and scenic drive from downtown Charlottesville, Crozet welcomes you with genuine hospitality and amazing mountain views. Afton, Greenwood, and White Hall are all within minutes of Crozet.

Afton Mountain Vineyards: 2021 Albariño

Sip award-winning wines in an all-weather glass pavilion while gazing at the Blue Ridge Mountains? Yes, please! Afton Mountain Vineyards’ vines were planted 45 years ago, making theirs one of the oldest in the state. Elevated at 1,000 feet on the eastern slope of Afton Mountain, the unique positioning of the vineyard allows grapes to thrive. And thrive they have, under the direction of winemaker Damien Blanchon, who has been at the helm for Afton since 2011.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: No
Maximum Group Size: 6
Offers overnight accommodations: Yes

Grace Estate Winery: 2021 First Baron Sauvignon Blanc

Focusing on agricultural tradition, Grace Estate creates 100% estate grown Virginia wines at their 450-acre Mount Juliet Farm, winery, and tasting room. You may be sensing a theme: Virginia wine tasting experiences go hand in hand with breathtaking views, and Grace Estate is no exception. Plan to pack a picnic, and enjoy a lovely afternoon sipping award-winning wines and snapping some selfies throughout your experience.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: No
Maximum Group Size: Tasting reservations required for parties of 10+
Offers overnight accommodations: No

King Family Vineyards: 2017 Meritage, 2019 Meritage, 2019 Petit Verdot, 2019 Brut Rosé, 2021 Mountain Plains Rosé, 2019 Small Batch Viognier, 2021 Viognier

Stewards of the land since 1998, King Family Vineyards is a family-owned and -operated winery now producing 10,000 cases per year. Classic and reserved tastings as well as vineyard tours are all options to gain a deeper understanding of the King Family wine program. If you’re visiting late spring through early fall, Sunday Polo at King Family is a tradition not to be missed. October 1, 2022 marked King Family’s 20th anniversary of the Tasting Room opening.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: No
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Pollak Vineyards: 2017 Meritage, 2019 Meritage, 2019 Merlot Reserve, 2019 Petit Verdot & 2021 Sauvignon Blanc

All of Pollak Vineyards’ wines are fully estate grown from their 34 acres of French vinifera – harvested by hand. Small batch, big flavor, and high quality is what you’ll find at Pollak. Cozy up by the fireplace in the tasting room on chilly days or bring a blanket and picnic near the pond during warm ones.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: Yes, for groups of 6+
Maximum Group Size: 12
Offers overnight accommodations: No

Stinson Vineyards: 2019 Meritage

Inspired by garagiste winemaking in France, Stinson is unique in both its technique as well as its design – a renovated three car garage designed by owner and architect Scott Stinson. Winemaking team Rachel Stinson Vrooman and Nathan Vrooman focus on European-style wine styles that emphasize subtlety and complexity. Enjoy a glass or bottle from the garage, featuring 360-degree mountain and vineyard views.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: Yes, for groups of 7+
Maximum Group Size: Call for details
Offers overnight accommodations: Yes

Veritas Winery: Scintilla, 2019 Petit Verdot & 2019 Veritas Reserve

Winemaker Emily Hodson’s philosophy is simple: allow the wine to show the beauty of where the grapes were grown, as well as a naturally balanced expression of the fruit by focusing on attention to detail and cultural practices. Emily is one of just a few woman winemakers who got her start in the Virginia wine industry and she has been at the helm for 15 harvests at Veritas. Plan a visit to enjoy these special varietals through a variety of experiences including tastings, food and wine pairings, picnics, and so much more.

Seasonal Outdoor Seating: Year-Round Outdoor Seating
Dog-Friendly: Yes, Outdoors
Reservations Required: Yes, for some experiences
Maximum Group Size: 8-10; depending on the experience
Offers overnight accommodations: Yes

Routes 20 and 29 head south from Charlottesville to the small town of Scottsville and rural communities of North Garden and Covesville. The landscape is dotted with rolling hills, working farms, and roadside refreshments such as Dr. Ho’s Humble Pie.

Albemarle CiderWorks: 2021 Orchard Blush & 2021 Wickson

Cideries throughout Virginia also compete in a special category of the Governor’s Cup. Albemarle CiderWorks was awarded 2023 Best in Show for its 2021 Orchard Blush.

A testimony to the enduring appeal and viability of family farms and innovative agricultural enterprise, Albemarle CiderWorks is first and foremost a nursery, cultivating more than 250 apple varieties to curate their library of Virginia hard ciders. Reservations are encouraged for parties of any size wishing to visit Albemarle CiderWorks. Guided tastings are available in addition to hard ciders by the glass, flight and bottle.

Be sure to check out their myriad of special events including heirloom apple tastings, live music, seasonal tours of their working orchard, and their farm stand which sells apples and seasonal fruit throughout the year.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: Yes, for groups 10+
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Delfosse Vineyards and Winery: 2020 Petit Verdot Reserve, 2021 Go-Go Girl & 2021 Screaming Hawk

Celebrate with Delfosse on winning the Governor's Cup this year! Hugged between the hills in Faber, Virginia, Delfosse enjoys the elevation to guarantee both flavorful wine and fabulous views. Tour their terraced vineyards (one of the only in Virginia), pack a picnic for outdoor lounging, or make a weekend of it when you book a stay in their 100+ year old Historic Chestnut Log Cabin, a peaceful respite overlooking the lake.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: n/a
Maximum Group Size: n/a
Offers overnight accommodations: Yes

Michael Shaps Wineworks: 2019 Chardonnay, 2019 Petit Manseng, 2019 Petit Verdot, 2020 Cabernet Franc, 2020 Meritage, 2020 Petit Verdot, 2020 Roussanne & 2020 Tannat

By 1995, Michael Shaps had accumulated numerous awards and acquired a reputation as one of Virginia’s up-and-coming winemakers. Now, nearly 20 years later, Michael continues to be a leader in Virginia wine as both an innovator and entrepreneur. Shaps offers two tasting room experiences. 1650 Harris Creek Road features indoor and expansive outdoor seating and offers traditional tastings of the Michael Shaps Virginia wines, as well as the Maison Shaps Burgundy wines--imported from Michael's winery in Meursault, France. Rustic and industrial, the Wineworks Extended tasting room is attached to the working warehouse, and offers everyday drinking wines in the Wineworks label, including flights, wine on tap, growlers, carafes, and bottles.

1650 Harris Creek Road
Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: For groups of 8+
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Wineworks Extended
Seasonal Outdoor Seating: Yes
Dog-Friendly: No
Reservations Required: contact the winery
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Pippin Hill Farm & Vineyards: 2017 Wild Acre Reserve, 2019 Petit Verdot, 2021 Cabernet Franc, 2021 Chardonnay, 2021 Petit Manseng & 2021 Sauvignon Blanc

A culinary vineyard, Pippin Hill’s focus is on garden and vine to table and creating fine Virginia wine experiences. Quite possibly the most Instagrammed winery in the state, Pippin Hill offers a variety of ways to enjoy elevated food and wine, perfectly documenting it all the while. Tastings, estate tours, cooking and wine schools, and fine dining Vintners Table experiences featuring multi-course meals are all possibilities. For a more casual excursion, make a reservation to sip and dine in the tasting room overlooking the grounds with million-dollar Blue Ridge views in the distance.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: For groups of 7+; highly recommended for table service for parties of any size
Maximum Group Size: Call for details.
Offers overnight accommodations: Yes

Wisdom Oak Winery: 2019 Chambourcin

Nestled on 126 acres, Wisdom Oak has multiple varietals planted including Chardonnay, Petit Manseng, Cabernet Sauvignon, Cabernet Franc and Merlot. A small batch boutique winery, owners Jason & Laura Lavallee have crafted a unique “off the beaten path” experience, like those they have most enjoyed while visiting winemaking regions around the world.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors
Reservations Required: For groups of 7+
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Set in the foothills of Virginia’s Piedmont region, Barboursville and Keswick are known for horse farms, historic estates, and pastoral landscapes.

Barboursville Vineyards: 2021 Fiano, 2021 Sauvignon Blanc Reserve & 2021 Vermentino Reserve

Barboursville's resident winemaker for more than 30 years, Luca Paschina holds the most diverse and extensive record of honors among all his peers in Virginia. According to Luca, “the estate of wine is a divine gift without borders, linking humanity and our diverse cultural backgrounds to their most elemental and their most celebratory nourishment.” Considered one of the leading wineries in Virginia, and also one of the oldest, Barboursville wine was selected to be served to Queen Elizabeth II during her 2007 visit to Virginia. Discover the newest vintages in the tasting room, then purchase a glass and enjoy a historic stroll around the Barboursville Ruins; Thomas Jefferson's mansion for Governor James Barbour which was mostly destroyed by a fire on Christmas Day 1884. Sip cellared vintages alongside culinary pairings in the Library 1821 as you overlook an expansive slope of Cabernet Franc and the Blue Ridge Mountains.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, Outdoors and in Discovery Tasting Room
Reservations Required: For groups of 6+ in the Library
Maximum Group Size: Call for details.
Offers overnight accommodations: Yes

Castle Hill Cider: 2020 Orchard Select & 2021 Serendipity

Founded in 2010, Castle Hill Cider was born after its owners decided to take Castle Hill back to its orchard roots. Colonel Thomas Walker, the original owner of Castle Hill Estate – and Thomas Jefferson’s legal guardian - was the first to bring Newtown Pippin apple scions to Central Virginia following his return from the Battle of Brandywine in 1777. The variety was planted at Castle Hill and became known as the Albemarle Pippin apple. Today, the estate boasts some 5,000 cider apple trees growing 40+ varieties. Cidermaker Don Whitaker aims to tell the tale of the terroir and history of the landscape in each glass of Castle Hill Cider. Nestled on 600 acres of rolling Virginia countryside is a stunning barn, which is home to the tasting room, production operation, and serves as a private event venue. Patio seating as well as groupings of Adirondack chairs dot the landscape while soft seating is available indoors. Hard cider by the glass, bottle, and flight is available as well as innovative cider cocktails and a light bites menu.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes
Reservations Required: No
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Chestnut Oak Vineyard: 2019 Nebbiolo & 2019 Petit Verdot

Small, modern, and mighty is the perfect way to describe Chestnut Oak Vineyard. Producing small batches of red and white varietals, in a beautiful and vibrant setting, their goal is to provide a wonderful Virginia wine tasting. Bonus: seating areas provide an up-close-and-personal view of the grapevines, creating a truly immersive experience. Plan a weekend visit to enjoy a picnic with friends on their lovely grounds.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes
Reservations Required: No
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Keswick Vineyards: 2021 Cabernet Franc & 2021 Trevillian Red

Dedicated to creating superior wines, Keswick Vineyards invites you to enjoy a relaxing afternoon on the covered porch or bring a picnic to enjoy al fresco while sampling some of its exclusive tasting room selections. New to the Keswick experience is a mini golf course, complete with wine barrels throughout to hold your glass. Beer and cider offerings round out the experience – Keswick truly offers something for everyone.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes – plus they have a dog park
Reservations Required: No
Maximum Group Size: Groups of 10+ can only be accommodated from 10am – 1pm
Offers overnight accommodations: No

Earlysville and Free Union feature smaller vineyards nestled along the eastern edge of Shenandoah National Park, a short drive northwest of downtown Charlottesville.

Hark Vineyards: 2019 Petit Manseng & 2021 Petit Manseng

Sustainability, great views, and wine all in one place! As outdoor lovers, Aaron and Candice Hark were careful to cultivate the land with both gathering spaces and places of quietude in mind. They also installed a 103-kilowatt solar panel system atop the winery building's roof, which will offset 3.7 million pounds of CO2 over the next 25 years. Enjoy wine and a BYO picnic (firepits are available during the winter) or purchase cheese, crackers, and even chocolate at the tasting room.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, outdoors
Reservations Required: No
Maximum Group Size: Call for details.
Offers overnight accommodations: No

Moss Vineyards: 2021 Moss Cider

Dramatic views and design alongside delectable wine – and cider – is what you’ll find at Moss Vineyards. Atop the mountain in Dyke, Virginia, Barry and Ellen Moss have created quite the getaway featuring small batch, estate grown wines and now a dry cider (the gold medal winner) for guest enjoyment. You’ll want to come prepared with outside food since you’ll be in no rush to leave this fairytale location.

Seasonal Outdoor Seating: Yes
Dog-Friendly: Yes, outdoors
Reservations Required: No
Maximum Group Size: Call for details.
Offers overnight accommodations: No

All of the wineries on the Monticello Wine Trail offer stunning and varied scenery. They are also defined by their people, including winemakers who are passionate about creating outstanding wines and sharing their knowledge. Plus, there are the generations of families who are committed to environmental stewardship and protecting agricultural life in the Charlottesville and Albemarle County area. Wineries within the Monticello Wine Trail are recognized as leaders in oenology and viticulture and maintain a supportive community. And there are many more amazing wineries not covered in this post!

Be sure to pair your wine-themed visit with Charlottesville and Albemarle County's renowned food scene and then stay a while to fully experience all the area has to offer!