June 1, 2026 (Charlottesville, VA) — The Monticello Wine Trail is proud to announce the 2026 Monticello Cup Gold Medal Winners, recognizing excellence in winemaking across the Monticello American Viticultural Area (AVA) and celebrating the depth, diversity, and continued momentum of Virginia wine.
Organized by wine educator and writer Frank Morgan, the Monticello Cup competition highlights standout wines from across the region, judged by an accomplished panel of wine professionals and industry leaders.
This year’s Gold Medal-winning wines showcase the remarkable range of the Monticello AVA, from sparkling wines and aromatic whites to age-worthy reds and innovative blends.
The Monticello Cup winner and Case Winners will be announced live during the Gold Medal Celebration on Friday, June 26 from 5:30–8:30 PM at Boar’s Head Resort as part of Monticello Wine Week.
The Gold Medal Celebration will feature an elevated cookout-style tasting experience with live music, more than 25 participating wineries, and the opportunity to taste Gold Medal-winning wines from across the region.
“We’re excited to celebrate the incredible quality and diversity of wines being produced across the Monticello AVA,” said Tracey Love, Executive Director of the Monticello Wine Trail. “The Gold Medal Celebration is designed to bring people together around great Virginia wine, food, music, and hospitality while showcasing the collaborative spirit that makes this region so special.”
2026 MONTICELLO CUP GOLD MEDAL WINNERS
- Afton Mountain Vineyards — 2024 Rosé Sparkling Wine Barboursville Vineyards — 2021 Nascent
- Barboursville Vineyards — 2023 Nebbiolo Reserve Cardinal Point Vineyard and Winery — 2025 Aubaine Chestnut Oak Vineyard — 2023 Cabernet Sauvignon Eastwood Farm and Winery — 2025 Petit Manseng Eastwood Farm and Winery — 2025 Rosé
- Fallen Tree Vineyard and Farm — 2021 Meritage Fallen Tree Vineyard and Farm — 2023 Bee Sting Red Flying Fox Vineyard and Winery — 2021 Trio
- Flying Fox Vineyard and Winery — 2023 Trio
- Grace Estate Winery — 2022 Gange-Rolv Chardonnay Hark Vineyards — 2023 Cabernet Franc
- Hark Vineyards — 2024 Roussanne
- Hazy Mountain Vineyards — 2024 Albariño Jefferson Vineyards — 2022 Meritage
- Jefferson Vineyards — 2023 Chardonnay Reserve Keswick Vineyards — 2024 Viognier Reserve
- King Family Vineyards — 2022 Mountain Plains Red
- King Family Vineyards — 2024 Viognier Knight’s Gambit — 2023 Cabernet Franc Knight’s Gambit — 2023 Meritage
- Loving Cup Vineyard & Winery — 2023 Tellurian Red Loving Cup Vineyard & Winery — 2025 Loving Cup White Michael Shaps Winery — 2021 En Hommage L Scott Michael Shaps Winery — 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 Pippin Hill Farm & Vineyards — 2025 Zero White Pollak Vineyards — 2023 Nebbiolo
- Southwest Mountains Vineyards — 2023 Cabernet Franc Reserve Southwest Mountains Vineyards — 2023 Chardonnay Reserve Stinson Vineyards — 2023 Mourvèdre
- Trump Winery — 2021 Blanc de Blanc Valley Road Vineyards — 2021 Meritage Valley Road Vineyards — 2024 Albariño
- Veritas Vineyards and Winery — 2023 Monticello White Woodbrook Farm Vineyard — 2024 Winterbourne
Monticello Wine Week takes place June 22–28, 2026 across Charlottesville and the Monticello AVA and includes winemaker dinners, vineyard events, a Rosé Festival, Sparkling Brunch, golf tournament, and immersive food and wine experiences throughout the region.
Tickets and lodging packages are now available.
For event details and tickets, visit: https://monticellowinetrail.com/taste-of
