Events

Live Music with Rain Mayo📅 Saturday, August 2 | 🕒 3 PM – 6 PM📍 James Charles Winery & Vineyard Join us for an afternoon of wine and music as...

Live Music with Chris Harasyn📅 Saturday, August 9 | 🕒 3 PM – 6 PM📍 James Charles Winery & Vineyard Spend your Saturday afternoon at James Charles Winery with live...

🐾 Yappy Hour at James Charles WineryFriday, August 15 | 4–7 PM Back by pup-ular demand—with an extra hour added so you can make it after work! Join us for...

Potato Sensations at Yappy Hour – Friday, August 15 | 4–7 PM 🥔 Join us at James Charles Winery for Yappy Hour and treat yourself to the ultimate comfort food...

Live Music with Lex Sacco📅 Friday, August 15 | 🕒 4–7 PM📍 James Charles Winery & Vineyard Spend your Friday evening with the unforgettable voice of Lex Sacco, a powerful...

🎶 Live Music with Nate HadleySaturday, August 23 | 3–6 PMJames Charles Winery Spend your Saturday afternoon in the vines with the acoustic sounds of Nate Hadley, a Winchester-based folk-Americana...

Saturday, September 6, 2025 | Noon – 7 |  James Charles Winery & Vineyard Cousins Maine Lobster Food Truck is rolling into James Charles Winery & Vineyard for a day of fresh,...

🍷 Live Music with Jayelynn Lee Saturday, September 6 | 4:00–700 PM Join us at James Charles Winery for an afternoon of live music with Jayelynn Lee. Her rich vocals...

🍖 Got dinner plans? Now you do! Join us Saturday, September 6th, from 4–8 PM at James Charles Winery & Vineyard for an evening of mouthwatering BBQ, live music, and...

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 cherished European tradition. At 2 PM, Rev. Bjorn C. Lundberg from Sacred Heart Catholic Church in Winchester will bless the vineyard, asking for grace and...

 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...