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  • Black Friday Special

    🍷 Black Friday at the WineriesFriday, November 28James Charles Winery & Vineyard | 12–8 PM After a long Thanksgiving filled with family, food, and festivities, you deserve a little you...

  • POSTPONED FOR FIRE BAN: Fire Pit Fridays

    November 28 | 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...

  • A Taste of Philippines Food Truck

    A Taste of Philippines James Charles Christmas Tree Lighting 🎄Saturday, December 6 • 3–8 PM Berryville’s own A Taste of Philippines LLC will be on-site serving fresh Filipino favorites during...

  • Christmas Tree Lighting

    🎄 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

    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

    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...

  • Fire Pit Fridays

    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...

  • Cousins Maine Lobster at the Winery

     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

     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...

  • Fire Pit Fridays

    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 Party

    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...