Monticello Wine Week
winemaker dinner
Charlottesville, VA
monticello wine week winemaker dinner
Thursday, June 25 | 6pm
$95/person plus tax + gratuity
All guests must be at least 21 years old to attend.
An Evening of Virginia Wine, Elevated
Experience Monticello Wine Week at UP on the Roof with a five-course dinner, expertly paired wines and the stories behind them.
Join us on June 25 for a one-night-only Winemaker’s Dinner at UP on the Roof, where Virginia’s celebrated wine country meets a thoughtfully crafted culinary experience. This year’s Monticello Wine Week dinner features a multi-course menu paired with distinctive wines from across the Monticello AVA — each selected to highlight the region’s depth, character and versatility. From bright sparkling selections to expressive whites and structured reds, every pairing is designed to complement the flavors of the season.
Seats are limited. Reservations are required.
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More Than Just a Dinner – It’s an Experience
This is a unique opportunity to connect with the people and stories behind the wines. Throughout the evening, you’ll hear directly from the winemakers of Veritas, Southwest Mountains, Loving Cup, Afton Mountain, Cunningham Creek and Hardware Hills as they share insight into their craft, their vineyards and what makes their corner of Virginia wine country such a remarkable place to grow and produce wine.
Whether you’ve been exploring the Monticello Wine Trail for years or you’re just starting to uncork your curiosity, this is your chance to taste, learn, and connect in a truly immersive way — all from the best seat in town.
A Perfectly Paired Menu
Expect a progression of flavors designed to surprise and delight — from vibrant seasonal starters to rich, indulgent mains and a bright, elegant finish.
Highlights include:
- A sparkling welcome pour paired with passed bites
- Brussels sprouts and bacon complemented by aromatic viognier
- Charred jumbo shrimp with tropical notes and a crisp rosé
- Duck confit tostada with a lively, fruit-forward red
- Grilled Wagyu steak paired with a bold, structured red blend
- A blackberry tart finale complemented by sparkling rosé
Don’t Miss Out on This One Night Only Event
Searching for things to do in Charlottesville? Want to learn more about Virginia winemaking and the Monticello Wine Trail? This wine dinner is ideal for:
- Date night that’ll actually impress
- A birthday, anniversary, or simply a celebration of summer
- Wine lovers ready to dive in and learn more about the Monticello AVA
- Groups looking for a Thursday night dinner that stands out
- Visitors looking to explore the best of Charlottesville’s food and wine scene
With sweeping rooftop views and perfect pairings, the Monticello Wine Week wine dinner event offers a more experiential alternative to traditional restaurant dining. This is one evening that’s gonna be hard to top.
Make a Reservation Today
Limited seats. Unlimited conversation. An unforgettable evening of Virginia wine, great food, and even better company — all above the rooftops of Charlottesville. Reserve your seat and discover the flavors, people and stories that define Monticello wine country.