Monticello Wine Week is Back
Last Updated on May 13, 2026 by Liz Thomson
If you love wine, this is your guide to one of the best weeks of summer!
Mark your calendars, Virginia foodies. Monticello Wine Week is returning June 22–28, 2026, and this year’s lineup might be the best one yet. Spread across Charlottesville and Central Virginia, the weeklong celebration brings together more than 40 wineries from the Monticello American Viticultural Area for an incredible series of events. Tickets and lodging packages are available now, and if last year was any indication, the standouts will go quickly.
Here’s what’s on the docket.
Tee Off with Winemakers (Monday, June 22)
The week kicks off with the fourth annual Golf Tournament at Spring Creek Golf Club. Players hit the links alongside Monticello winemakers, sipping wines from across the region between holes. Proceeds support the Monticello Wine Trail’s nonprofit work, so you can feel good about that mid-round pour.
Winemaker’s Dinners, Two Ways (Thursday, June 25)
Thursday brings a choose-your-own-adventure moment: two simultaneous Winemaker’s Dinners are happening, with thirteen wineries split between them. Up on the Roof in downtown Charlottesville offers a rooftop vibe, while Birdwood Mansion at Boar’s Head Resort serves up something a little more stately. Both feature multi-course pairings and the chance to hear winemakers talk about their vineyards and vintages firsthand.
The Gold Medal Celebration (Friday, June 26)
If you only make it to one Wine Week event, make it this one. The Gold Medal Celebration at Boar’s Head Resort is the week’s signature event — a walk-around tasting with more than 20 wineries, live music, and cookout-style food spread across a tented turf lawn. The night wraps with the announcement of the Monticello Cup winner, the region’s top honor. With around 250 guests expected, it’s the place to be on Friday night. (We love Boar’s Head!)
Rosé All Afternoon (Saturday, June 27)
Saturday afternoon goes pink! Hark Vineyards is hosting the Monticello Rosé Festival, featuring rosés from up to 15 Wine Trail producers alongside live music and an easy outdoor setting. Bring sunglasses. And maybe bring your camera because this venue is gorgeous.
The “Feast of Reason” Dinner (Saturday, June 27)
New this year, and maybe the most intriguing event on the schedule, is the “Feast of Reason” dinner, a collaboration with Monticello itself. Hosted by Eastwood Farm and Winery at its new Virginia Wine Collective production facility, the family-style dinner pairs Wine Trail bottles with a menu from James Beard nominee Chef Leah Branch of The Roosevelt, alongside storytelling from Emmy Award–winning food historian Deb Freeman. Expect a meal that’s as much about land, agriculture, and community as it is about what’s on the plate. There’s so much to love about this mash-up of talent!
Sparkling Brunch Sendoff (Sunday, June 28)
Closing out the week is a Sparkling Brunch at Hazy Mountain Vineyards — bubbles, chef-driven brunch stations, and the kind of mountain views that make you want to call out of work Monday. A graceful way to wind things down in Afton.
Whether you’re a longtime Virginia wine fan or just looking for something interesting to add to your summer calendar, Wine Week is a great chance to taste your way through the region. Grab tickets while you can, and we’ll see you in Charlottesville!
