Live Music with Chris Harasyn Saturday, September 13 | 3–6 PMJames Charles Winery & Vineyard Come celebrate the Blessing of the Harvest with live music following afterwards. 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 favorite wine....
Yappy Hour- Final One! September 19, 2025 | 4 – 7 PM We’re closing out our Yappy Hour season with a Harvest-themed celebration for you and your four-legged friends! Fall Fun: Snap a photo at our pumpkin patch photobooth Local Dog Vendors: Shop treats, gear, and more from returning favorites Live Music: Enjoy the sounds of Jim...
Live Music with Jim Snedeker Friday, September 19 | 4:00–7:00 PM Spend your Friday afternoon at James Charles Winery with live music by Jim Snedeker. He will be performing during our final Yappy Hour of the season, so bring your dog and enjoy $7 glasses of wine while you listen! With over five decades of...
Karaoke Night at James Charles WineryFriday, September 26 | 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, September 26 from 7–10 PM for a fun-filled evening of singing, sipping, and great vibes, hosted by the high-energy team at...
Bluegrass & Bites: Murphy’s Bluegrass Bandits Sunday, September 28 | 1:00–4:00 PMJames Charles Winery & VineyardFREE EVENT with optional $25 Bites Join us for Murphy's Bluegrass Bandits playing live at James Charles Winery, along with delicious elevated Bites for just $25. Each plate will come with Fried Pickles, Jalapeno Corn Fritters, Bourbon Meatballs, and South...
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...
