🦞 Cousins Maine Lobster is Coming to James Charles Winery! 🍷Saturday, June 7 | 12–6 PM4063 Middle Rd, Winchester, VA Join us for a delicious afternoon at the winery as the nationally acclaimed Cousins Maine Lobster Truck rolls into town! From buttery lobster rolls and creamy bisques to lobster tacos, tots, and more—this is your...
🎶 Live Music with Bryan BaxterSaturday, June 7 | 3–6 PMJames Charles Winery & Vineyard Join us for an afternoon of live music with Bryan Baxter, a Winchester native known for his soulful, genre-blending sound. From bluegrass and folk to blues, rock, and Americana, Bryan’s performances are heartfelt and full of personality. With a mix...
Friday, June 14 | 1–4 PM Uncle Buddy is Back!Kick off the summer season with sizzling flavors and smooth sips at our first grilling event of the summer! Join us for Grill & Chill with Dad, featuring mouthwatering eats from Uncle Buddy’s Catering, perfectly paired with your favorite James Charles wines. While it’s the perfect...
🎶 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 favorite known for his rich blend of country, Americana, and acoustic rock. With decades of experience and a background that spans regional bands and solo...
🎶 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 20 years of experience, Rachel delivers soulful vocals across country, pop, and rock—drawing inspiration from legends like Patsy Cline, Adele, and Stevie Nicks. Her nostalgic...
🦞 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 Winery with their famous lobster rolls, crab rolls, and more New England–style bites. Pair your favorite wine with fresh seafood and soak up the vineyard...
🎶 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 U.S. Navy veteran whose musical journey began with a Harmony acoustic guitar and a Ramones mixtape. Self-taught and left-handed, Michael brings a unique and heartfelt...
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 returns to James Charles with an acoustic set full of timeless rock, modern favorites, and heartfelt vocals that pair perfectly with a glass of your...
🐾 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 and your pup are invited to be part of the fun! Enjoy:🐶 Local vendors like Golden Nibbles & Fairfax Pet Portraits📸 A doggie photobooth by...
🎶 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....