Monticello Wine Week, sponsored by the Monticello Wine Trail, will take place June 22–28, 2026, across Charlottesville and the surrounding Central Virginia region. This annual celebration highlights the depth, quality, and collaborative spirit of the Monticello American Viticultural Area (AVA), bringing together more than 40 wineries, hospitality partners, and visitors from across the country.
Tracey Love, the new (and first) Executive Director of the Monticello Wine Trail, explains “What excites me most about this role is the opportunity to connect people. Not just to great wine, but to the stories, farms, landscapes, and people behind it. Monticello Wine Week reflects the collaborative spirit of this region, and I’m excited to help continue growing that energy while welcoming more visitors to experience the Monticello AVA.”
Wine Week begins on Monday, June 22 with the fourth annual Golf Tournament at Spring Creek Golf Club, where guests will play alongside Monticello winemakers while enjoying wines from across the region. Love explains that the tournament was Stephen Barnard’s idea (the winemaker at Keswick Vineyards). Players will try the participating winemaker’s wines along the fairway, and following the tournament there will be a lunch. “We already have some teams put together,” says Love, adding that Kelly Cornett, of the “Cork in the Road” podcast, is coming from Atlanta.
On Thursday, June 25, two simultaneous Winemaker’s Dinners will take place at Up on the Roof in downtown Charlottesville and Birdwood Mansion at Boar’s Head Resort. Thirteen wineries will participate across both dinners, pairing wines with multi-course menus and sharing insights into their vineyards, vintages, and winemaking philosophies. Love explains that this idea came from a couple of years ago, when some local restaurants would reach out to wineries about doing a local wine dinner that became “dinner on the roof”.
The week’s signature event, the Gold Medal Celebration, will be held on Friday, June 26 at Boar’s Head Resort. This walk-around tasting will feature more than 20 wineries, live music, and a cookout-style format on the tented turf lawn. The evening will culminate in the announcement of the Monticello Cup winner, recognizing excellence in the region. Attendance is projected at approximately 250 guests. The Trail partnered with the Boar’s Head for this; the Inn offers a lodging special that includes the Gold medal tasting to encourage people to register and stay as well as attend the tasting.
On Saturday, June 27, Hark Vineyards will host a Monticello Rosé Festival, a lively afternoon event featuring rosé wines from across the Monticello Wine Trail, paired with live music and a relaxed outdoor setting. Up to 15 wineries are expected to participate.
New this year is a special “Feast of Reason” dinner in collaboration with Monticello. Hosted by Eastwood Farm and Winery at its new production facility, the Virginia Wine Collective, this immersive, family-style experience will feature Emmy Award–winning food historian Deb Freeman and James Beard nominee Chef Leah Branch of The Roosevelt. Wines from Monticello Wine Trail wineries will be paired throughout, telling a story of land, agriculture, and community.
Love explains that Justin Reid, who works with Monticello, created conversation cards based on Jefferson’s dinners, to spark conversation about James Hemmings and his brother who cooked for Jefferson, and the food history that they brought to Monticello. The Trail partnered with Eastwood since they have a chef, and decided to invite Deb Freeman, a Virginia culinary historian and writer. She made a documentary about the pioneering African American chef Edna Lewis, and will speak on that. “We’ll have the conversation cards at the dinner, and Freeman willl lead the conversation.”
The week concludes on Sunday, June 28 with a Sparkling Brunch at Hazy Mountain Vineyards, featuring sparkling wines, chef-driven brunch stations, and sweeping mountain views in a relaxed, celebratory setting. New for 2026, Boar’s Head Resort joins as the presenting lodging partner, offering curated overnight packages that bundle accommodations with Wine Week events,
Tickets and curated lodging packages are now available, offering guests the opportunity to experience multiple events throughout the week while exploring Virginia wine country.
To order tickets for these Monticello Wine Week events, visit https://monticellowinetrail.com/taste-of.