What is the Monticello Cup?

It's a blind-judged wine competition among wines made from grapes grown along the Monticello Wine Trail, with results revealed each fall at the Gold Medal Celebration.

Where is the Monticello Wine Week celebration held?

The culminating Gold Medal Celebration is held at Boar's Head Resort in Charlottesville.

Who organizes Monticello Wine Week?

It's organized by the Monticello Wine Trail, the collective of Charlottesville and Albemarle County wineries.

Are dates and tickets confirmed for this year's event?

Not in our records — this listing has shown no recent activity, so confirm current dates, hours, and ticketing directly with the Monticello Wine Trail before planning your visit.

Monticello Wine Week: Charlottesville's Fall Wine Event

Monticello Wine Week is the Charlottesville-area wine trail's flagship annual event, built around the Monticello Cup, a blind-judged competition among wines made from Monticello Wine Trail grapes. The week closes with the Gold Medal Celebration at Boar's Head Resort, where the winning wines are announced and poured for the public.

What it is: A week-long celebration of Monticello Wine Trail wineries, anchored by the Monticello Cup competition.
Where it culminates: Gold Medal Celebration at Boar's Head Resort, Charlottesville.
Organizer: Monticello Wine Trail.
Where to learn more: monticellowinetrail.com/monticello-cup.

A note on planning: our records show no recent social activity or updated details for this event, so treat specifics like this year's exact dates, hours, and ticket pricing as unconfirmed until you check directly with the Monticello Wine Trail. It's worth confirming the event is still running as described before building a trip around it.

Why the Monticello Cup Matters

Unlike a tasting-room happy hour or a single winery's release party, the Monticello Cup is a competitive judging — wines from across the Monticello Wine Trail are entered and evaluated, and the results aren't known until the Gold Medal Celebration itself. For wine-club members and collectors who already know the Trail's bigger names, it's a chance to see which bottles the judges actually rewarded that year, not just which ones have the best marketing.

What to Expect at the Gold Medal Celebration

Held at Boar's Head Resort, the Gold Medal Celebration is built around pouring the competition's winners for attendees — a public-facing capstone to a week that otherwise runs behind the scenes at member wineries. It's the kind of event that rewards showing up with an open afternoon rather than a tight schedule, since the point is unhurried tasting rather than a packed agenda. Exact dates, hours, and admission details aren't confirmed in our records, so check the Monticello Wine Trail directly before you go.

Planning Ahead in Fall Wine Season

Monticello Wine Week lands during the Piedmont's broader fall wine season, when the Charlottesville and Albemarle County trail is already at its busiest with harvest-adjacent events. If Wine Week is the anchor of your visit, it's worth building the rest of a Charlottesville weekend around it — the city's downtown dining scene and its museums are an easy complement to a day spent on the wine trail.

Planning Your Visit

Monticello Wine Week and the Monticello Cup
Location: Charlottesville, Albemarle County, VA — culminating event at Boar's Head Resort
Organizer: Monticello Wine Trail
Website: Monticello Wine Week and the Monticello Cup
Note: dates, hours, and ticketing were not confirmed in our records as of this writing — verify current details before planning your visit.

Round Out the Trip

Charlottesville's Downtown Mall area offers a full day beyond the wine trail itself — the The Fralin Museum of Art at UVA and Kluge-Ruhe Aboriginal Art Collection both make sensible detours if you're staying overnight for Wine Week and want a slower morning before the afternoon's tastings.