Events

Live Music with Jim Snedeker Friday, September 19 | 4:00–7:00 PM Spend your Friday afternoon at James Charles Winery with live music by Jim Snedeker. He will be performing during...

Karaoke Night at James Charles WineryFriday, September 26 | 7–10 PMJames Charles Winery & Vineyard Grab the mic and your favorite glass of wine—Karaoke Night is back at James Charles!...

Bluegrass & Bites: Murphy’s Bluegrass Bandits Sunday, September 28 | 1:00–4:00 PMJames Charles Winery & VineyardFREE EVENT with optional $25 Bites Join us for Murphy's Bluegrass Bandits playing live at...

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...