Events

🎶 Live Music with Jeff TaultonSaturday, June 14 | 3–6 PMJames Charles Winery & Vineyard Join us for an afternoon of music with veteran singer-songwriter Jeff Taulton, a Western Maryland...

🎶 Live Music with Rachel BrinkmeierSaturday, June 21 | 3–6 PMJames Charles Winery & Vineyard Join us for a relaxing afternoon of wine and live music with Rachel Brinkmeier. With...

🦞 Ned’s Food Truck at James Charles Winery📅 Saturday, June 28 | ⏰ 12–5 pm Get ready for a delicious summer afternoon! Ned’s Food Truck is rolling into James Charles...

🎶 Live Music with Michael JonesSaturday, June 28 | 3–6 PMJames Charles Winery & Vineyard Join us for an afternoon of wine and live music with Michael Jones, a retired...

Buddy Dunlap & Brennan Edwards Duo Live at Bluegrass & Bites | Sunday, June 29 | 1–4 PM The Buddy Dunlap & Brennan Edwards Duo will be performing in the tasting room, bringing a lively mix of traditional bluegrass and heartfelt originals. Buddy is a born entertainer on guitar and vocals, and Brennan blends his...

🎶 Bluegrass & Bites at James Charles Winery 🎶Sunday, June 29 | 1 PM – 5 PM Join us for an unforgettable afternoon of music, wine, and mouthwatering bites! The Robert Mabe Band will be bringing their signature bluegrass sound live in the Tasting Room, setting the perfect tone for a laid-back Sunday escape. For...

🎶 Live Music with Chris Harasyn 🎶Saturday, July 5 | 3–6 PMJames Charles Winery & Vineyard Kick off your holiday weekend with live music, wine, and vineyard views! Chris Harasyn...

🐾 Yappy Hour at James Charles Winery 🐾Friday, July 11 | 4–6 PMDog-Friendly | Indoors & Out We’re thrilled to launch our very first Yappy Hour at James Charles—and you...

🎶 Live Music with Lex Sacco 🎶Saturday, July 12 | 3–6 PMJames Charles Winery & Vineyard Join us for a vibrant afternoon of music, wine, and vineyard views with the incredible Lex Sacco! Known for her powerhouse vocals and genre-spanning performances—from pop to country to crowd-favorite classics—Lex brings the energy and charm to every set....

Live Music with Nate Hadley Saturday, July 19 | 3–6 PM James Charles Winery & Vineyard Join us for an afternoon of wine and live music with Nate Hadley, a Winchester-based folk-Americana artist known for his rich acoustic sound and heartfelt lyrics. Drawing inspiration from artists like Tyler Childers and The Lumineers, Nate blends modern...

🎶 Live Music with Rachel Brinkmeier at James CharlesThursday, July 25 | 7–10 PM Join us for a magical summer night at James Charles Winery with live music from the incredibly talented Rachel Brinkmeier, performing from 7 to 10 PM! Known for her soulful voice and acoustic storytelling, Rachel brings a blend of heartfelt originals...

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 during the Delta Aquarids meteor shower—a perfect excuse to slow down and look up. Bring the family, spread out on the lawn, or watch from...