The Monticello Wine Trail has officially announced 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.
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