Monticello Wine Week

Mark your calendars for June 5th thru June 8th, 2025. Uncork the anticipation! Get ready for a week-long celebration of exquisite wines and unforgettable experiences along the Monticello Wine Trail.


Winemaker’s Dinner

Thursday, June 5th,

6-8pm

Rooftop at The Doyle

Indulge in an unforgettable evening of fine wine and elevated cuisine at our Winemaker’s Dinnes, hosted on the Rooftop at The Doyle. Featuring a thoughtfully curated multi-course menu, expertly paired with six award-winning wines from the Monticello AVA. Meet the winemakers behind these celebrated wines as they share insights into their craft, vineyard stories, and what makes Monticello’s terroir so unique. Whether you're a seasoned connoisseur or new to Virginia wines, this is a rare opportunity to experience the intersection of culinary artistry and winemaking excellence. $95 per person

Ticket Link Coming Soon!


Gold Medal Celebration

Friday, June 6th

5:30pm - 8pm

The Bradbury

Join us on Friday, June 6th at The Bradbury on Charlottesville’s vibrant Downtown Mall for an evening dedicated to the finest wines of the Monticello Wine Trail. The Monticello Cup Gold Medal Celebration will feature award-winning wineries from the Monticello Case, culminating in the live announcement of the Monticello Cup winner.

Meet the winemakers behind these exceptional wines, hear from special guest speakers, and experience the excitement firsthand. Enjoy a curated selection of wines paired with delicious cuisine from Harvest Moon Catering, all in an elegant and lively setting.

Event Highlights:

Taste wines from 12+ Monticello Wine Trail wineries, including the Monticello Cup winner

Meet the winemakers behind these award-winning wines

Hear from special guest speakers about Virginia’s dynamic wine scene

Enjoy cuisine from Harvest Moon Catering

Experience the live announcement of the Monticello Cup winner

Celebrate excellence in Virginia winemaking and be part of this prestigious event. Get your tickets today!


Rosé Picnic

Saturday, June 7th

12pm - 2pm

Soak in breathtaking vineyard views while enjoying an idyllic Rosé Picnic Lunch—the perfect way to relax and embrace the essence of Monticello Wine Week. Your curated picnic basket will include a delicious gourmet lunch, thoughtfully paired with refreshing rosé wines from the Monticello Wine Trail. Lounge on the grass or at a private table, sip wine with friends, and immerse yourself in the tranquil vineyard setting. Whether you're a devoted rosé lover or simply looking for a serene afternoon with excellent food and wine, this event promises an unforgettable experience of good vibes, great company, and even better wine

Ticket Link Coming Soon!


Sparkling Brunch

Sunday, June 8th

11am - 2pm

Start your day in style with our Sparkling Brunch, where the effervescence of Monticello’s best sparkling wines meets the indulgence of a delicious brunch spread. Set in a picturesque countryside location, this elegant yet relaxed affair invites you to savor bubbly delights alongside classic brunch favorites, all while basking in the warmth of Virginia’s springtime beauty. Whether you prefer crisp blanc de blancs, lively pét-nats, or delicate rosé sparklers, there’s a glass to suit every palate. Toast to the day ahead and celebrate the magic of Monticello Wine Week with every sip.

Ticket Link Coming Soon!


Wine Week Sponsors

We are proud to partner with Keswick Hall as our Presenting Sponsor