Events

Blessing of the Harvest September 13, 2025 All are invited to join hands with us on Saturday, September 13th for our annual Blessing of the Harvest at James Charles Winery—a...

 Live Music with Chris Harasyn Saturday, September 13 | 3–6 PMJames Charles Winery & Vineyard Come celebrate the Blessing of the Harvest with live music following afterwards. Chris Harasyn returns to...

Yappy Hour- Final One! September 19, 2025 | 4 – 7 PM We’re closing out our Yappy Hour season with a Harvest-themed celebration for you and your four-legged friends!  Fall...

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...