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May 7 – 12, 2018 – Charlottesville, Va

Grand Tasting Event at Sprint Pavilion: Saturday, May 12

Taste of Monticello Wine Trail

“Monticello Wine Trail… Birth Place of American Wine”

2018 will bring the seventh annual Taste of Monticello Wine Trail Festival back to Charlottesville’s Downtown Mall. The Central Virginia community has embraced this event and made it into a spring tradition. Last year, the event boasted record attendance with numbers coming close to capacity. This year, the festival continues with a steady upward movement and expanded programming with regional & national coverage.

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Monday, May 7

Monticello Cup Awards at the Jefferson Theater

  • An exciting event for the wine enthusiast, taste award-winning wines from the 2018 Monticello Cup Wine Competition along side the winegrowers and winemakers who made them.
  • Tickets: $49
  • Time: 6-10pm

More info at

Friday, May 11

Individual wineries will host a variety of activities during the day followed by a series of winemaker dinners at some of Charlottesville’s best restaurants that evening.

Options include a Rosé Lunch, Sparking Wine Brunch, several winery tours and more!

  • For a full list local wineries hosting meals plus other exciting Friday events, visit the Friday Events page!

Saturday, May 12

Grand Tasting Event at Sprint Pavilion

  • Grand Tasting Event at Sprint Pavilion featuring 25 local wineries and live entertainment An exclusive VIP ticket is available and offers catered food and an opportunity for sampling exclusive wines from each winery.
  • Wine tastings on Saturday will be limited to one flight of tastings per winery with the purchase of your ticket. Extra wine can be purchased by the glass or bottle.
  • Time: 1:30-5:30 p.m. (VIP ticket holders gain early entry at 12:30pm).

Participating Vineyards

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Friday, May 11 Events

A day of showcase winery events highlighting the dynamic food and wine culture present within the Monticello AVA.

Attend a Sparkling Brunch, Rosé Lunch or other winemaker events on Friday afternoon.

For a full schedule and event descriptions, visit the Friday Events page.



Take your Taste of Monticello Wine Festival experience to the next level – with VIP Passes! Enjoy complimentary hors d’oeuvres, sample exclusive VIP-only wines, relax in the seating area and talk with the local vintners who produce the wine.


Plus if you need to step away while you’re tasting wines from the 25+ local vineyards in attendance, you’ll have access to private luxury VIP restrooms.

Omni Hotel Charlottesville

212 Ridge McIntire Road
Charlottesville, VA

More info

Residence Inn

315 W Main St.
Charlottesville, VA

More info

Graduate Charlottesville

1309 W Main St.
Charlottesville, VA

More info

Live Music from Hard Swimmin’ Fish

Hard Swimmin’ Fish is an ensemble deeply rooted in the traditions of American music. Their down home roots sound pilfers from the best that early American music has to offer including blues, jazz, funk and swing, and churn it all up into a spicy brew that is familiar yet uniquely their own. Frederick (MD) magazine chose Hard Swimmin’ Fish “Best Original Band” in 2016 and 2018.

Monticello Cup Awards – Friday 5/7

Join us for an exciting evening of celebrating quality wines alongside the winegrowers and winemakers of the Monticello AVA. Guests will taste gold and silver award-winning wines from the 2018 Monticello Cup Wine Competition, each category paired with heavy hors d’oeuvres.
The 3 Top Ranking Whites and 3 Top Ranking Reds will be announced, as well as who takes home the prestigious Monticello Cup for the highest overall scoring wine.
Tickets + info at

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