The 33rd annual Monticello Cup Awards ceremony took place at the opening event of the 2024 Monticello Wine Week, a full week of celebrations honoring the Monticello Wine Trail and the best wines of the Monticello American Viticultural Area (AVA.) The Monticello AVA won the coveted Wine Enthusiast Wine Region of the Year Award in 2023, competing against illustrious regions from California, France and Italy. As a result the Monticello Wine Trail, always a popular destination, is experiencing a boom in tourism and interest in the wine industry. To be entered in the competition, a wine must contain at least 85% fruit from the Monticello AVA and be produced by a member of the Monticello Wine Trail.

The 2024 Monticello Cup Winner

The winner of Charlottesville’s 2024 Monticello Cup was King Family Vineyards’ 2021 Mountain Plains Red, their popular red blend. This marks the second big win of the year for the established Crozet-based winery after their Meritage wine won the 2024 Virginia Governor’s Cup competition. The 2024 Monticello Cup Competition took place at the historic Wool Factory in Charlottesville. The opening night gala kicked off a week of events celebrating the Monticello Wine Trail’s successes.

King Family Vineyards’ Mountain Plains Red is a Bordeaux-style red blend aged in new French barrels for 22 months. Rich dense layers of complexity with dark fruits and silky tannins give way to an exquisite wine. The blend for the 2021 vintage is 45% Cabernet Franc, 37% Merlot and 18% Petit Verdot. The name “Mountain Plains” comes from the original land grant for the land the vineyard currently occupies, a nod to the winery’s heritage.

The 2024 Monticello Cup Case Honored in Charlottesville

The Monticello Cup Case included the Cup winner and the other 11 top scoring wines of the competition. The Cup Case wines showcased a healthy mix of single varietal wines as well as red and white blends from across the Charlottesville area AVA.

The 2024 Monticello Cup Case

Barboursville Vineyards — 2015 Octagon

Cunningham Creek Winery — 2019 Herd Dog Red

Eastwood Farm & Winery — 2023 Petit Manseng

Keswick Vineyards — 2019 Cabernet Sauvignon

Loving Cup Vineyard — 2023 Loving Cup White

Michael Shaps Wineworks — 2021 L. Scott

Pollak Vineyards — 2021 Meritage

Trump Winery — 2021 New World Reserve

Valley Road Vineyards — 2023 Albariño

Veritas Vineyards & Winery — 2021 Momentarius: Monticello White

Veritas Vineyards & Winery — 2021 Veritas Reserve

The Monticello AVA Wine Week

The Monticello AVA celebrated winning the Wine Region of the Year award in style. They organized a plethora of Charlottesville area events throughout the week. They celebrated Rosé wines in style with a lake picnic at Trump Winery. Mount Ida Farm and Vineyard hosted a Sparkling wine brunch against the picturesque Virginia countryside. Event sponsor Keswick Hall, a premiere luxury resort in Virginia Wine Country, hosted a Winemaker golf tournament on their award-winning golf course. They then hosted a Winemaker Reception that evening where guests mingled with Monticello Wine Trail winemakers, enjoying delicious Virginia wine and hors d’ouvres provided by Keswick Hall’s award winning Marigold restaurant.

Charlottesville wineries, Gold Winning Wines, Monticello Wine Trail, Monticello Cup 2024, The Wool Factory

The Monticello Wine Trail of the Charlottesville area has two highly anticipated annual events other than the Monticello Cup, both of which were included in the Monticello Wine Week. The annual Red Wine Showcase took place at Barboursville Vineyards. The winery’s Palladio Restaurant offered delicious gourmet fair to pair with the award-winning Monticello red wines, and VIP guests even got to sample some of their special varietals from the Library collection. Eastwood Farm & Winery hosted the White Wine showcase, offering tastings of the bright Monticello white wines, mingling with winemakers and artisan food pairings.

Gold-Winning Wines from the 2024 Monticello Cup Awards

The History of Charlottesville’s Monticello Wine Trail

When it comes to Virginia Wine Country, Charlottesville wineries are one of the east coast’s top destinations. There are over 40 wineries along the Monticello Wine Trail representing varied Virginia terroir and a long history of winemaking dating all the way back to Thomas Jefferson’s initial attempts at establishing a Virginia wine industry. The Monticello AVA we know today has its roots in the 1970s when the Zonins, an Italian winemaking family, founded Barboursville Vineyards. The industry has been blossoming ever since.

To see who won the Monticello Cup in recent years, read more on the 2023 Monticello Cup Competition, the 2022 Monticello Cup Competition and the 2020 Monticello Cup Winner. ~




Virginia Wine & Country celebrates elevated living in Virginia Wine Country. Virginia Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The Virginia Wine & Country Gold Book is an annual guide to the top award-winning wines, wineries and experiences in Virginia Wine Country. The annual Virginia Wine & Country Wedding Planner is an art book of elegant Virginia weddings. Virginia Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media also provides branding, web design and PR services for the wine industry.