Events

Friday, July 25 | 8–11 PMLive Music by Rachel Brinkmeier | 7–10 PM Join us at James Charles Winery for a magical summer night of wine, live music, and stargazing...

🎤 Live Music with Austin NemithSaturday, July 26 | 3–6 PMJames Charles Winery & Vineyard Join us for a soulful afternoon as Austin Nemith brings his authentic Americana sound to...

Saturday, August 2, 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 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 our next Yappy Hour, where dogs and their humans come together for wine, treats, and tail-wagging fun. Whether you're stopping by for the first time...

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 from Potato Sensations! They’ll be serving up perfectly baked potatoes, crispy seasoned fries, and mouthwatering loaded creations like The Cajun Way, Loaded BBQ, and The...

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 and emotive performer whose music blends roots rock, country, and pop influences. Known for her rich vocals and expressive songwriting, Lex delivers both original songs...

🎶 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 artist. Known for his rich, heartfelt vocals and rootsy storytelling, Nate draws inspiration from artists like The Lumineers and Tyler Childers. His warm, honest sound...

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, mouthwatering seafood! Indulge in Maine-style lobster rolls, creamy bisque, flavorful tacos, and more, all perfectly paired with your favorite award-winning wines.

🍷 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 and acoustic charm make the perfect pairing for a glass of wine and a September day in the vineyard. Sit back, sip, and savor the...

🍖 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 great wine! Bam Bam’s BBQ, based in Stephens City, VA, is a competition BBQ team turned mobile food and catering sensation—known for traveling all over...