Monticello Wine Trail

06/01/2026

Monticello Wine Week Returns June 22–28

There’s something special happening in Virginia wine country right now.

The Monticello AVA continues to gain national recognition for the quality and diversity of its wines, but what truly defines this region is the collaborative spirit behind it. The wineries, growers, chefs, artists, historians, hospitality teams, and community members all helping shape what Virginia wine looks like today.

Monticello Wine Week returns June 22–28, 2026 with a full week of events across Charlottesville and the surrounding region designed to celebrate exactly that.

This year’s lineup includes winemaker dinners, vineyard experiences, live music, golf, sparkling wine, rosé, food pairings, storytelling, and immersive conversations around wine, culture, and hospitality. More than 40 wineries from across the Monticello Wine Trail are participating alongside incredible regional partners.

Gold Medal Celebration at Boar’s Head Resort

Friday, June 26 | 5:30–8:30 PM

This year’s signature event brings together more than 25 wineries pouring Gold Medal-winning wines from the 2026 Monticello Cup competition. Hosted at Boar’s Head Resort, the evening features an elevated cookout-style format with live music, incredible Virginia wine, and the live announcement of the Monticello Cup winner and Case Winners.

Feast of Reason at the Virginia Wine Collective

Saturday, June 27

One of the most anticipated additions to Wine Week this year, Feast of Reason has officially sold out. Inspired by Jefferson’s legendary “feasts of reason,” the immersive multi-course dinner is co-sponsored by Thomas Jefferson’s Monticello and The Getting Word African American History Project at Monticello and features Emmy-winning documentarian and food historian Deb Freeman alongside James Beard-nominated Chef Leah Branch of The Roosevelt.

Guests will gather around wines from Jefferson Vineyards, Eastwood Farm and Winery, Wound Tight from Septenary Winery, and ZC Wine from the Virginia Wine Collective for an evening centered around conversation, foodways, land, history, and community.

Winemaker Dinners

Thursday, June 25

Two simultaneous wine dinners will take place at Birdwood Mansion at Boar’s Head Resort and Up on the Roof in downtown Charlottesville, featuring 13 wineries paired with collaborative multi-course menus and winemaker storytelling.

Rosé Festival at Hark Vineyards

Saturday, June 27

Spend the afternoon in Earlysville tasting rosé wines from across the Monticello AVA with live music, food, and summer vineyard views.

Sparkling Brunch at Hazy Mountain Vineyards

Sunday, June 28

Wine Week concludes with sparkling wines, brunch stations, and panoramic mountain views at one of the region’s most scenic vineyard destinations.

Monticello Wine Week continues to evolve into something much bigger than a traditional wine festival. It’s a reflection of the energy, creativity, and momentum happening throughout Virginia wine country right now, and an invitation to experience it firsthand.

Tickets and lodging packages are now live.

We can’t wait to welcome you to the Monticello AVA this June.

https://monticellowinetrail.com/taste-of

Monticello Wine Week Returns June 22–28 There’s something special happening in Virginia wine country right now. The Monticello AVA continues to gain national recognition for the quality and diversity of its wines, but what truly defines this region is the collaborative spirit behind it. The wine...

05/24/2026

Long weekends hit different in Virginia wine country 💫

Vineyard views, chilled rosé, live music, and unforgettable moments across the Monticello Wine Trail. From Charlottesville to the heart of the Monticello AVA, we’re raising a glass to community, connection, and remembering those who served 🇺🇸

Which winery is on your weekend itinerary? ✨

05/23/2026

🥍🍷 Championship Weekend is here in Charlottesville, and the Monticello Wine Trail is proud to welcome the lacrosse community with open arms (and full glasses).

From multigenerational lacrosse families at Pollak Vineyards and King Family Vineyards to special championship weekend experiences across the trail, this weekend is a reminder of how deeply sports, hospitality, wine, and community are connected here in Charlottesville.

🥍 Pollak Vineyards is pouring a special Lacrosse Championship Flight featuring four standout wines, plus a complimentary bonus pour for game ticket holders.

🥍 Blenheim Vineyards is offering 10% off all weekend long for guests who bring their lacrosse ticket stub, with plenty of space to relax under the tent overlooking the vines.

Whether you’re cheering at Scott Stadium, reminiscing on your own lacrosse days, or simply looking for a place to unwind between games, our wineries are ready to welcome you all weekend long with award-winning Virginia wine, scenic views, and local hospitality 🥂

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05/20/2026

🏅Meet the 2026 Monticello Cup GOLD Medal Winners ✨

The wines are shining and the Monticello AVA understood the assignment 👏 From crisp whites and sparkling wines to bold reds and cellar-worthy blends, this year’s gold medal lineup is stacked.

Now it’s time to taste them for yourself 🥂

Join us Friday, June 26 at the Gold Medal Celebration at Boar’s Head Resort where these wineries will be pouring their award-winning wines all night long 🍇

Tickets will sell out, so don’t wait.

🥂Cheers to the 2026 GOLD winners:
Afton Mountain Vineyards • Barboursville Vineyards • Cardinal Point • Chestnut Oak • Eastwood • Fallen Tree • Flying Fox • Grace Estate • Hark • Hazy Mountain • Jefferson • Keswick • King Family • Knight’s Gambit • Loving Cup • Michael Shaps • Mountain & Vine • Oakencroft • Pippin Hill • Pollak • Southwest Mountains • Stinson • Trump Winery • Valley Road • Veritas • Woodbrook Farm

05/18/2026

The frost hit hard across the Monticello AVA this spring, but the vines are already pushing forward 🌱

From Loving Cup, Pollak, Keswick, Barboursville, and Fallen Tree, we’re seeing new growth and tiny flower clusters emerge. Hopeful signs that this season’s story is still being written 🍇

The crop may be smaller this year, but the resilience of the vineyards (and the people working them) never ceases to amaze us.

05/14/2026

A full week of wine, food, conversation, celebration, and community across Charlottesville and the Monticello AVA featuring more than 40 wineries and incredible regional partners.

⛳ June 22 — Golf Tournament at Spring Creek Golf Club

🍽 June 25 — Winemaker’s Dinners at Birdwood Mansion at Boar’s Head Resort + Up on the Roof

🏅 June 26 — Gold Medal Celebration + Monticello Cup announcement at Boar’s Head Resort

🌸 June 27 — Rosé Festival lunch at Hark Vineyards

🕯 June 27 — Feast of Reason Dinner with Leah Branch, Deb Freeman, Monticello at Virginia Wine Collective

🥂 June 28 — Sparkling Brunch at Hazy Mountain Vineyards

A huge thank you to our presenting sponsor Boar’s Head Resort and to the many winery hosts, chefs, community partners, restaurants, hotels, and small businesses helping bring this week to life.

This is Virginia wine country at its best!

Tickets and lodging packages are now live at the link in bio 🥂

05/14/2026

🗞️Honored to see the Monticello Wine Trail featured by Heather Bien in StyleBlueprint as one of the South’s “5 Fabulous Wine Weekends.” From vineyard views and award-winning wines to incredible food, hospitality, and Blue Ridge scenery, there’s a reason so many travelers are discovering the Monticello AVA.

With more than 40 wineries throughout the region, a weekend here can look however you want it to. From long lunches overlooking the vines, downtown dinners, mountain sunsets, and discovering new favorite wines along the way.

Thank you to and for including Charlottesville alongside some of the South’s most exciting wine destinations 🍇

05/10/2026

Mother’s Day itinerary:
☀️ Vineyard views
🥂 A glass of Virginia wine
🧺 Maybe a market, brunch, or bouquet workshop
💐 Time together 💞

Sounds like a pretty perfect Sunday to us.

Happy Mother’s Day from the Monticello Wine Trail ❤️

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