Monticello Wine Week
Monticello Wine Week returns June 22–28, 2026, with a full week of events in and around Charlottesville celebrating the Monticello AVA from June 22 through June 28, 2026.
Join us in raising a glass to the craftsmanship, character, and community of the Monticello AVA!
Winemaker’s Golf Tournament at Spring Creek Golf Club
Monday, June 22
9am-2pm
Spring Creek Golf Club
Kick off Wine Week with the fourth annual golf tournament featuring Monticello Wine Trail winemakers and wines from the Monticello AVA. Breakfast pasties and lunch are included in ticket cost. Wines from the Monticello Wine Trail will be served along the course!
Up On The Roof at The Doyle Hotel
Thursday, June 25th,
6-8pm
This winemaker’s dinner features a multi-course menu paired with thoughtfully selected wines and storytelling from the winemakers themselves. Expect a progression from bright, welcoming wines through expressive whites, structured reds, and a balanced finish with dessert pairings. $95 per person
Participating Wineries: Veritas • Afton Mountain • Southwest Mountains • Cunningham Creek • Hardware Hills • Loving Cup
Dinner at Birdwood Mansion
Thursday, June 25th
6pm - 10pm
Birdwood Mansion
This winemaker’s dinner features a multi-course menu paired with thoughtfully selected wines and storytelling from the winemakers themselves. Expect a progression from bright, welcoming wines through expressive whites, structured reds, and a balanced finish with dessert pairings.
Participating wineries: King Family • Hark • Flying Fox • Septenary • Eastwood • Blenheim • Trump Vineyards
Gold Medal Celebration
Friday, June 26th
5:30pm - 8pm
Boar’s Head Resort
Our signature event of the week takes place on the tented turf lawn and brings together 25+ wineries for a walk-around tasting. Enjoy an elevated cookout-style evening with live music as we announce the Monticello Cup winner.
Boar’s Head Resort will also offer lodging packages that bundle room nights with Wine Week experiences, including access to this event.
Experience the live announcement of the Monticello Cup winner and celebrate excellence in Virginia winemaking and be part of this prestigious event. Get your tickets today!
Ken Farmer & The Authenticators will be performing from 5:30-8:30 p.m. (with breaks throughout the evening)
RAIN BACKUP
Should weather not permit for the event to be outdoors, the event will be moved inside to the Pavilion at Boar's Head Resort. Tickets are non-refundable.
Monticello Rosé Festival at Hark Vineyards
11am - 2pm
Hark Vineyards
A lively, festival-style afternoon featuring rosé wines from across the Monticello Wine Trail, paired with live music and a relaxed vineyard setting. With up to 15 wineries expected, this will be one of the most vibrant gatherings of the weekend.
Participating Wineries: Hazy Mountain Vineyards, Loving Cup Vineyard & Winery, King Family Vineyards, Eastwood Farm and Winery, Trump Winery, Afton Mountain Vineyards, Hardware Hills Vineyard, Southwest Mountains Vineyards, Veritas Vineyards, Flying Fox Vineyard, Hark Vineyards, Cunningham Creek Winery
Feast Of Reason Dinner
Saturday, June 27
6-8:30pm
Virginia Wine Collective
In collaboration with Monticello and aligned with Civic Season and Virginia 250, this special dinner brings together wine, food, and facilitated conversation. Monticello Wine Trail wines will be paired with a guided dialogue exploring themes of land, history, and community.
Sparkling Brunch
Sunday, June 28th
11am - 1pm
Hazy Mountain Vineyards
Close out the week with a relaxed brunch featuring sparkling wines from Monticello Wine Trail wineries, chef-driven brunch stations, and sweeping mountain views. A bright, celebratory finish to the week.
Participating Wineries: Hazy Mountain Vineyards, King Family Vineyards, Eastwood Farm and Winery, Trump Winery, Afton Mountain Vineyards, Hardware Hills Vineyard, Veritas Vineyards, Flying Fox Vineyard
Wine Week Sponsors
We are proud to partner with Boar’s Head Resort as our Presenting Sponsor