May 12, 2026 (Charlottesville, VA) — The Monticello Wine Trail announces the return of Monticello Wine Week, taking 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.
Tickets and curated lodging packages are now available, offering guests the opportunity to experience multiple events throughout the week while exploring Virginia wine country.
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. The tournament is expected to raise funds in support of the Monticello Wine Trail’s nonprofit mission.
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.
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.
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.
We’re also introducing 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.
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, making it easier for guests to experience the full week.
Monticello Wine Week continues to grow as a premier regional event, driving tourism, supporting local agriculture, and strengthening the economic impact of Virginia’s wine industry.
