🎶 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....
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...
🎤 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 the vineyard. A West Virginia native with deep roots in folk, country, bluegrass, and funk, Austin delivers passionate original songs and crowd-pleasing covers that resonate...
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, 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 Rain Mayo📅 Saturday, August 2 | 🕒 3 PM – 6 PM📍 James Charles Winery & Vineyard Join us for an afternoon of wine and music as Rain Mayo takes the stage at James Charles Winery. Known for her rich vocals and soulful acoustic style, Rain blends indie, folk, and pop influences...
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 music from local favorite, Chris Harasyn. A Winchester-based singer-songwriter, Chris brings a heartfelt mix of original tunes and classic covers with smooth acoustic style and...
🐾 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...
