The Monticello Wine Trail presented the 2026 Monticello Cup during Monticello Wine Week on Friday, June 26, at Boar’s Head Resort in Charlottesville. Central Virginia’s premier wineries gathered to pour their gold medal-winning wines and celebrate this year’s winners.
The Monticello Wine Trail Grand Tasting
In 2026, the Monticello Wine Trail awarded 37 gold medals to exceptional wines, all competing for the coveted Monticello Cup. Under the direction of wine writer and acclaimed wine judge Frank Morgan, the wines underwent multiple rounds of blind taste testings to determine the ultimate winner, as well as the other top-performing wines.
Among the gold medal winners were Michael Shaps Winery (seen being poured above at top right) and Keswick Vineyards (below at top left). Below at bottom, Barboursville Vineyards (left), who won the 2026 Virginia Governor’s Cup, and Afton Mountain Vineyards (right) poured tastings of their own gold-winning wines, accompanied by live music, delicious food and mingling with friends.
The Monticello Wine Trail’s 2026 Gold-Winning Wineries
Cup Case Winners
- Afton Mountain Vineyards | 2024 Rosé Sparkling Wine
- Barboursville Vineyards | 2023 Nebbiolo Reserve
- Chestnut Oak Vineyard | 2023 Cabernet Sauvignon
- Eastwood Farm and Winery | 2025 Rosé
- Fallen Tree Vineyard and Farm | 2021 Meritage
- Flying Fox Vineyard and Winery | 2023 Trio
- Hark Vineyards | 2023 Cabernet Franc (Cup Winner)
- Hark Vineyards | 2024 Roussanne
- Hazy Mountain Vineyards | 2024 Albariño
- King Family Vineyards | 2022 Mountain Plains Red
- Southwest Mountains Vineyards | 2023 Cabernet Franc Reserve
- Veritas Vineyards and Winery | 2023 Monticello White
Gold Winners
- Barboursville Vineyards | 2021 Nascent
- Cardinal Point Vineyard and Winery | 2025 Aubaine
- Eastwood Farm and Winery | 2025 Petit Manseng
- Fallen Tree Vineyard and Farm | 2023 Bee Sting Red
- Flying Fox Vineyard and Winery | 2021 Trio
- Grace Estate Winery | 2022 Gange-Rolv Chardonnay
- Hazy Mountain Vineyards | 2024 Albariño
- Jefferson Vineyards | 2022 Meritage, 2023 Chardonnay Reserve
- Keswick Vineyards | 2024 Viognier Reserve
- King Family Vineyards | 2022 Mountain Plains Red, 2024 Viognier
- Knight’s Gambit | 2023 Cabernet Franc, 2023 Meritage
- Loving Cup Vineyard & Winery | 2023 Tellurian Red, 2025 Loving Cup White
- Michael Shaps Wineworks | 2021 En Hommage L Scott, 2023 Petit Manseng
- Mountain & Vine Vineyards and Winery | 2022 Screaming Hawk Meritage
- Oakencroft Farm & Winery | 2023 White Table Wine
- Pippin Hill Farm & Vineyards | 2021 Ridge Reserve, 2025 Zero White
- Pollak Vineyards | 2023 Nebbiolo
- Southwest Mountains Vineyards | 2023 Chardonnay Reserve
- Stinson Vineyards | 2023 Mourvèdre
- Trump Winery | 2021 Blanc de Blanc
- Valley Road Vineyards | 2021 Meritage, 2024 Albariño
- Woodbrook Farm Vineyard | 2024 Winterbourne
Meet the Leaders of the Monticello Wine Trail
The Monticello Wine Trail has undergone several changes lately, including an change in leadership and structure. Dave Kostelnik (seen below at top right), who oversees management and operations at Southwest Mountains Vineyards, succeeded Veritas Vineyards’ George Hodson as president. Tracey Love, marketing manager at Blenheim Vineyards (seen below, top left, with Kostelnik), became the Monticello Wine Trail’s first executive director, overseeing the organization’s day-to-day operations.
Hark Vineyards Wins the 2026 Monticello Cup
Hark Vineyards won the 2026 Monticello Cup for their 2023 Cabernet Franc. Their other gold-medal winner, their 2024 Roussanne, also earned a place in the 2026 Monticello Cup Case, making them the only winery with two wines in the acclaimed collection. Winemaker AJ Greely (seen below in red) accepted the award from Virginia’s Secretary of Agriculture Katie Frazier. This marks the first time Hark Vineyards has won the prestigious award. Greely, who also serves as President of the Virginia Vineyards Association, expressed gratitude for the recognition.
Greely (seen above left, at far right next to Secretary Frazier and Morgan) accepted the well-deserved accolade with aplomb. “I always say the most important thing for me is to be part of this industry because of how close we are,” Greely said in her acceptance speech, “how great the Virginia [wine] industry is, and because we work together to lift one another up.” ~
MAI LIONNI GUSS is a writer and editor whose work is shaped by a love of language, landscape, and the lives people build within them. As a writer and lead editor for Wine & Country Life, she crafts stories that celebrate luxury lifestyle and wine culture with nuance and heart. She holds advanced degrees in literature, with a particular focus on Shakespeare. When she isn’t writing, Mai works in animal rescue, where she channels that same care and attention into helping animals find safe, lasting homes.
R. L. JOHNSON is our co-publisher and creative director, Robin Johnson Bethke, who began her career as a professional photographer in Los Angeles before moving into graphic design and art direction when she relocated to Charlottesville in 1994. As our company’s co-founder and visionary, she enjoys all aspects of the publishing process from story conception to graphic design to photography. Her work is often seen in many of our publications.
