Celebrate Monticello Wine Trail Wine Week with exceptional wine experiences across Virginia wine country. While these events are not hosted at Trump Winery, we are proud to participate and invite guests to join the Trump Winery team at featured partner locations throughout the week.
Monticello Wine Trail Winemaker’s Golf Tournament
Monday, June 22, 2026 | 9:00 AM–2:00 PM
Spring Creek Golf Club
Join Trump Winery for an unforgettable start to Monticello Wine Week at the fourth annual Winemaker’s Golf Tournament at Spring Creek Golf Club, featuring championship golf, exceptional Virginia wines, and the rare opportunity to play alongside members of the Trump Winery executive team. Enjoy breakfast pastries, curated tasting stations, lunch, raffle prizes, and a memorable day on the course with Monticello Wine Trail winemakers while supporting local nonprofit organizations.
Dinner at Birdwood Mansion
Thursday, June 25 | 6:00–9:00 PM
Birdwood Mansion | Charlottesville, VA
Join Trump Winery at Birdwood Mansion for an elegant multi-course winemaker dinner featuring expertly paired wines, culinary experiences, and storytelling from participating winemakers.
Gold Medal Celebration
Friday, June 26 | 5:30–8:30 PM
Boar's Head Resort | Charlottesville, VA
Join us for Monticello Wine Week’s signature event featuring 25+ wineries, walk-around tastings, live music, and elevated cookout-style fare on the tented turf lawn. The evening concludes with the highly anticipated announcement of the Monticello Cup winner.
Lodging packages will also be available through Boar’s Head Resort, offering overnight accommodations paired with select Wine Week experiences.
Sparkling Brunch Showcase
Sunday, June 28 | 11:00 AM–1:00 PM
Hazy Mountain Vineyards | Afton, VA
Join Trump Winery at Hazy Mountain Vineyards for a sparkling brunch experience featuring gourmet action stations and tastings from eight Monticello AVA wineries, all set against scenic summer mountain views.