Bluegrass & Bites Sunday, September 28th 1-5PM Join us at James Charles Winery on Sunday, September 28th from 1pm-5pm for free event Bluegrass & Bites! Enjoy Murphy's Bluegrass Bandits live in the Tasting Room, along with delicious Elevated Bites for just $25 (purchase tickets ahead of time). Each plate will come with fried pickles, jalapeno...
Live Music with Bryan BaxterSaturday, October 4 | 3–6 PM 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 of original songs, timeless covers,...
Live Music with Rachel Brinkmeier – Saturday, October 18 | 3–6 PMJames Charles Winery 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 sound and...
October 24 | 4:00 PM – CloseJames Charles Winery & Vineyard As the evenings grow cooler, there’s no better way to unwind than fireside with a glass of wine in hand. Join us for Fire Pit Fridays at James Charles — cozy up by the flames, take in the beauty of fall, and sip your...
Karaoke Night at James Charles WineryFriday, October 24 | 7–10 PMJames Charles Winery & Vineyard Grab the mic and your favorite glass of wine—Karaoke Night is back at James Charles! 🎤🍷 Join us Friday, October 24 from 7–10 PM for a fun-filled evening of singing, sipping, and great vibes, hosted by the high-energy team at...
October 31 | 4:00 PM – CloseJames Charles Winery & Vineyard As the evenings grow cooler, there’s no better way to unwind than fireside with a glass of wine in hand. Join us for Fire Pit Fridays at James Charles — cozy up by the flames, take in the beauty of fall, and sip your...
Sunday, November 2, 2025 | 12 – 5 PM 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. No reservations needed—just show up, grab some lobster, and enjoy...
Join us for Paws & Purrs: Howl-O-Wine at the Vineyard on Wednesday, November 5, 4-7 PM, at James Charles Winery & Vineyard — an evening of wine, Billy Sous food truck, music, and pet-friendly fun! Enjoy live music, a pet costume contest, a drawing, and free pet portraits — all while supporting Blue Ridge Care’s...
Join us November 7–11 as we honor VA250 Week and the 250th birthday of the United States Marine Corps with $2.50 tastings for non-club guests at all three of our tasting rooms. Explore a flight that highlights seasonal favorites and signature pours while we commemorate this historic milestone.
Flag Opening Ceremony📅 Friday, November 7 | 2:00 PM Join us at James Charles Winery as we begin the VA 250 commemorative week with a special Flag Opening Ceremony & Historic Military Display, presented in partnership with the Winchester Rotary Club. This patriotic event will feature a visual display of U.S. flags, antique military vehicles,...
November 7 | 4:00 PM – CloseJames Charles Winery & Vineyard As the evenings grow cooler, there’s no better way to unwind than fireside with a glass of wine in hand. Join us for Fire Pit Fridays at James Charles — cozy up by the flames, take in the beauty of fall, and sip your...
Now hear this! Now hear this! James Charles Bogaty, a US Marine and this winery's namesake, invites you to celebrate the 250th birthday of the Marine Corps! Please join us on Saturday, 8 November 2025 from 1800-2300 (6:00-11:00 PM). This event is open to United States Marines, past or present, and their guests. A social...
