Wine Week in Full Swing
Monticello Wine Week brings the Gold Medal Celebration and Rosé Festival this weekend — plus Final Fridays at Pollak, a summer boil at Blue Mountain, and Sunday polo at King Family. Here’s your guide to 41 events across 25 venues in Charlottesville wine country.
Featured Event
Final Fridays Concert: Side Hustle
Pollak Vineyards — Greenwood, VA · Friday, June 27 · 5:30 – 8:30 PM · Free Admission
Every last Friday of the month, Pollak Vineyards opens the patio for their Final Fridays Concert Series — and this month they’ve got Side Hustle. The band brings a high-energy mix of rock, pop, and funk covers to an estate winery set at the foot of the Blue Ridge. Whistle Stop Grill food truck rounds out the evening.
This Friday: Side Hustle with Whistle Stop Grill food truck — patio opens at 5:30 PM. Free, all ages welcome. Get event details →
Friday — June 26
Wine week opens — with oysters, strings, and gold medals
Sunset Soirée: South River Strings & Oyster Catcher Sea Farms — Chisholm Vineyards · 6:00 PM – 9:00 PM
One of the most atmospheric Friday nights of the summer — South River Strings playing live on the vineyard as the sun drops behind the Blue Ridge, with fresh oysters from Oyster Catcher Sea Farms shucked on-site. Get details →
MWT Gold Medal Celebration — Boar’s Head Resort, Charlottesville · 5:30 PM – 8:30 PM
25+ local wineries pour on the tented lawn at Boar’s Head, with heavy hors d’œuvres, live music from Ken Farmer & The Authenticators, and the live announcement of the Monticello Cup winner. GA $80, VIP $125. Get tickets →
Veritas Supper Series — Basque Country — Veritas Vineyard and Winery · 6:30 PM
Regional ingredients and bold Spanish flavors, each course paired with Veritas estate wines. $100 per person including wine pairings. Wine club members get 20% off the first two tickets. Reserve a seat →
Saturday — June 27
Rosé festival, a summer boil, and brilliant jazz
Monticello Rosé Festival — Hark Vineyards · 11:00 AM – 2:00 PM
Monticello Wine Week wraps up Saturday at Hark Vineyards with the Rosé Festival — walk-around tasting with 12 trail wineries, live music, sweeping vineyard views, and picnic-style food. GA $65, Wine Only $40. Get tickets →
Low Country Boil — Blue Mountain Brewery · 12:00 PM – 6:00 PM
Shrimp, crawfish, sausage, corn, and potatoes — $26 for the full platter. Live music from Copacetic 1–4pm. Also releasing Key Lime on Acid in cans and on draft for the first time. Get details →
Robert Jospé Trio — Glass House Winery · 5:00 PM – 8:00 PM
One of the area’s most acclaimed jazz acts returns to Glass House Winery in Free Union. High-energy world-class jazz in the conservatory — grab a glass of wine or a beer and settle in. Get details →
Sunday — June 28
Polo and pink wine to close it out
Roseland Polo — King Family Vineyards · 12:00 PM – 4:00 PM · Free Admission
Free and open to the public, every Sunday through November. Pack a blanket, grab a bottle from the tasting room, and watch matches against the backdrop of the Blue Ridge. Gates open 10am, matches at noon and 2pm. Get details →
Rosé All Day — Michael Shaps Wineworks · 12:00 PM – 4:00 PM
An exclusive flight of four rosés — Virginia, French, Sparkling Malbec, and a preview of the unreleased 2024 — paired with fresh seafood from Crozet Seafood Supply and live jazz funk from The Norms. Get details →
Browse all events at weekendr.info.