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.


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

Event Details to Come Soon

Sparkling Brunch

Sunday, June 8th

11am - 2pm

Event Details to Come Soon


Wine Week Sponsors

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