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  • Cousins Maine Lobster at the Winery

     Sunday, November 2, 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...

  • Paws & Purrs: Howl-O-Wine with Blue Ridge Care

    Join us for Paws & Purrs: Howl-O-Wine at the Vineyard on Wednesday, November 5, 4-7 PM, at James Charles Winery & Vineyard — an evening of wine, Billy Sous food...

  • $2.50 Tastings for VA250 Week

    Join us November 7–11 as we honor VA250 Week and the 250th birthday of the United States Marine Corps with $2.50 tastings for non-club guests at all three of our...

  • VA 250 Week: Flag Opening Ceremony

    Flag Opening Ceremony📅 Friday, November 7 | 2:00 PM Join us at James Charles Winery as we begin the VA 250 commemorative week with a special Flag Opening Ceremony &...

  • Fire Pit Fridays

    November 7 | 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...

  • 250th USMC Birthday Ball

    Now hear this! Now hear this! James Charles Bogaty, a US Marine and this winery's namesake, invites you to celebrate the 250th birthday of the Marine Corps! Please join us...

  • VA 250 Week: Veterans Groups Open House

    📍 James Charles Winery & Vineyard📅 Sunday, November 9 | 2:00 PM – 4:00 PM Join us at James Charles Winery as we honor those who have served with a...

  • VA 250 Week: Historical Uniform Display

    250 Birth of the Marine Corps – Historical Uniform Display 📍 James Charles Winery & Vineyard 📅 Monday, November 10 | 2:00–4:00 PM On exhibit will be antique Marine Corps...

  • VA 250 Week: Closing Ceremony

    📅 November 11 | 2:00 PM Closing Ceremony MC: Les Veach, Mayor of Winchester Speaker: Col. Giles Kyser, USMC (Retired) Guard: Sgt. Sanchez, USMC Blessing: Sacred Heart Catholic Church –...

  • Paella Day

    Saturday, November 15 • 12-6 PMLive Latin Music: 3–5 PM Savor Spanish flavors and vineyard views at our fall Paella Day. The Paella and Tapas Place food truck will be...

  • Paella Day: Live Latin Guitar with Jarrett Laskey

    Paella Day: Live Latin Guitar with Jarrett LaskeySaturday, November 15 • 3–5 PM Settle in with a glass of wine and a plate of paella while Jarrett Laskey sets the...

  • POSTPONED FOR FIRE BAN: Fire Pit Fridays

    November 21 | 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...