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!
Winemaker Dinner
Up On The Roof
Thursday, June 25th
6pm - 8:30pm
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 - 9pm
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 - 8:30pm
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.
Make a Weekend Out of it!
Wine Week Room Package
with Gold Medal Celebration Tickets at Boar’s Head Resort
Book your Wine Week stay package now and receive luxurious overnight accommodations and VIP tickets for each guest to the Gold Medal Celebration.
About the Gold Medal Celebration
As the signature event of the week, this festive celebration takes place on The Green just behind The Spa and brings together more than 25 wineries for a walk-around tasting. Enjoy an elevated cookout-style evening and be there when the Monticello Cup winner is announced. Live music will be provided by Ken Farmer and The Authenticators.
Monticello Rosé Festival at Hark Vineyards
11am - 2pm
Hark Vineyards
Join us for a vibrant afternoon at Hark Vineyards as part of Monticello Wine Week, celebrating rosé in all its forms. Set against sweeping vineyard views, this festival-style gathering brings together 12 Monticello Wine Trail wineries for a walk-around tasting of the region’s most refreshing and expressive wines.
Your General Admission ticket includes a tasting of one rosé from each participating winery, along with a visit to the buffet line by The Catering Outfit, featuring seasonal, picnic-style fare. Guests can relax on the lawn, enjoy live music, and move freely between indoor and outdoor spaces designed for connection and discovery.
Additional ticket options are available for food-only or tasting-only experiences.
Come spend the afternoon exploring, tasting, and celebrating summer in Virginia wine country.
Participating wineries: Hazy Mountain, Loving Cup, King Family, Eastwood, Afton Mountain, Hardware Hills, Southwest Mountains, Hark, Cunningham Creek, Jefferson, Valley Road Vineyards.
Feast Of Reason Dinner
Saturday, June 27
6-8:30pm
Virginia Wine Collective
Eastwood presents Feast of Reason, a special dinner designed to invite conversation and highlight local chefs and wines.
In collaboration with Monticello, Eastwood Farm and Winery presents Feast of Reason at its new production facility, the Virginia Wine Collective in Charlottesville, Virginia. This will be an immersive, family-style dinner featuring Emmy-award winning food historian, Deb Freeman and James Beard nominee Chef Leah Branch of The Roosevelt. Wines from the Monticello Wine Trail will be paired throughout, helping tell a story of land, agriculture, and community.
This is a dinner designed to invite conversation and discuss questions that shape our civic life. Gathering around the table to share food and ideas has long been a powerful tool for strengthening community. The dinners that Jefferson hosted at Monticello and at the White House were known for remarkable food and conversation. Inspired by this timeless tradition and the extraordinary legacy of enslaved chefs such as Edith Hern Fossett and James and Peter Hemings, Feast of Reason creates space for curiosity, listening, and meaningful conversation.
Leah Branch is a Virginia native and James Beard Foundation Semifinalist for Best Chef: Mid-Atlantic (2026). A graduate of Johnson & Wales University, Leah brings over 20 years of culinary experience, ranging from catering and baking to executive chef leadership. Recognized as a Richmond Dining All-Star and one of the city’s Top 40 Under 40, her work at The Roosevelt reflects a deep commitment to Southern cuisine and a thoughtful exploration of regional foodways, with features in Garden & Gun, Eater, and the Cooking Channel.
Deb Freeman is an Emmy Award–winning documentarian, writer, and leading voice on Black foodways. As the host of Finding Edna Lewis and the award-winning podcast Setting the Table, Deb brings a powerful perspective on the intersection of race, culture, and food, guiding the evening’s conversation through history.
Seating is limited for this one-night event.
Co-Sponsors:
Thomas Jefferson's Monticello
Getting Word African American History Department
Sparkling Brunch Showcase
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, Stinson 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