Events

Bluegrass & Bites Sunday, September 28th  1-5PM Join us at James Charles Winery on Sunday, September 28th from 1pm-5pm for free event Bluegrass & Bites! Enjoy Murphy's Bluegrass Bandits live...

 Live Music with Bryan BaxterSaturday, October 4 | 3–6 PM Join us for an afternoon of live music with Bryan Baxter, a Winchester native known for his soulful, genre-blending sound....

Live Music with Rachel Brinkmeier – Saturday, October 18 | 3–6 PMJames Charles Winery  Join us for a relaxing afternoon of wine and live music with Rachel Brinkmeier. With 20 years...

October 24 | 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...

Karaoke Night at James Charles WineryFriday, October 24 | 7–10 PMJames Charles Winery & Vineyard Grab the mic and your favorite glass of wine—Karaoke Night is back at James Charles!...

October 31 | 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, 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...

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...

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...

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 & Historic Military Display, presented in partnership with the Winchester Rotary Club. This patriotic event will feature a visual display of U.S. flags, antique military vehicles,...

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...

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...