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 at James Charles Winery & Vineyard. Grab a sweet treat, sip wine, and enjoy a festive night.
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 us during VA250 week, and they’re back to help light up the night with festive songs throughout the event. 🎶
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 hand. Join us for Fire Pit Fridays at James Charles — cozy up by the flames, take in the beauty of winter, and sip your...
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 lobster rolls, creamy bisque, flavorful tacos, and more, all perfectly paired with your favorite award-winning wines. No reservations needed—just show up, grab some lobster, and...
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 acoustic charm make the perfect pairing for a glass of wine and Cousins Maine Lobster food truck. Sit back, sip, and savor the winter weekend...
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 hand. Join us for Fire Pit Fridays at James Charles — cozy up by the flames, take in the beauty of winter, and sip your...
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 winter chill and treat yourself to a delicious afternoon at our newest immersive tasting experience: The Art of the Toast. This intimate, ticketed event pairs...
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...
Live Music with Brad the Guitar GuySaturday, January 24 • 2–5 PM Join us at James Charles Winery & Vineyard for an afternoon of live music with Brad the Guitar Guy. Brad the Guitar Guy is a professional solo acoustic artist based in the Winchester, Virginia area. He is well-known in the DMV (DC, Maryland,...
