Events

🎄 Please join us for our annual Christmas Tree Lighting at James Charles Winery on December 6, from 6-9PM. 🎄 There will be live music by the Windsong Community Chorus,...

Cotton Candy Princess Food Truck James Charles Christmas Tree LightingSaturday, December 6 • 6–9 PM Berryville’s own Cotton Candy Princess will be spinning fresh cotton candy during the tree lighting...

Windsong Community Chorus James Charles Christmas Tree Lighting 🎄 Saturday, December 6 • 6–9 PM Enjoy classic Christmas music from the Windsong Community Chorus, an all-women ensemble. They performed with...

December 12 | 4:00 PM – CloseJames Charles Winery & Vineyard As the evenings grow cooler, there’s no better way to unwind than fireside with a glass of wine in...

 Sunday, December 14, 2025 | 12 – 5 PM Cousins Maine Lobster Food Truck is rolling into James Charles Winery & Vineyard for a day of fresh, mouthwatering seafood! Indulge in Maine-style...

 Live Music with Jayelynn Lee Sunday, December 14 | 2:00–5:00 PM Join us at James Charles Winery for an afternoon of live music with Jayelynn Lee. Her rich vocals and...

December 19 | 4:00 PM – CloseJames Charles Winery & Vineyard As the evenings grow cooler, there’s no better way to unwind than fireside with a glass of wine in...

VA250 Kickoff at James Charles Winery Sunday, January 11 • 2–4 PM Free • Open to the Public Kick off a year of local events celebrating America’s 250th anniversary at...

The Art of the Toast: A Grilled Cheese & Wine PairingSaturday, January 17 Time Slots: 12 PM • 2 PM • 4 PM (10 tickets per session) Warm up from the...

Live Music with Jim SnedekerSaturday, January 17 | 2:00–5:00 PMVeramar Vineyard Jim Snedeker will be performing live from 2 to 5 PM, bringing his easygoing mix of classic tunes and...

Trivia Night at James Charles Winery & VineyardThursday, January 23 • 7–10 PMFree • Open to the Public Put your knowledge to the test and join us for Trivia Night...

Cousins Maine Lobster at James Charles Winery & VineyardSaturday, January 24 • 12–6 PM Get ready, lobster lovers! Cousins Maine Lobster is rolling into James Charles Winery & Vineyard for a full day of that classic Maine flavor. Join us on Saturday, January 24 from 12–8 PM and enjoy your favorite lobster dishes while you...