🎶 Live Music with Nate HadleySaturday, August 23 | 3–6 PMJames Charles Winery Spend your Saturday afternoon in the vines with the acoustic sounds of Nate Hadley, a Winchester-based folk-Americana artist. Known for his rich, heartfelt vocals and rootsy storytelling, Nate draws inspiration from artists like The Lumineers and Tyler Childers. His warm, honest sound...
Saturday, September 6, 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 Jayelynn Lee Saturday, September 6 | 4:00–700 PM Join us at James Charles Winery for an afternoon of live music with Jayelynn Lee. Her rich vocals and acoustic charm make the perfect pairing for a glass of wine and a September day in the vineyard. Sit back, sip, and savor the...
🍖 Got dinner plans? Now you do! Join us Saturday, September 6th, from 4–8 PM at James Charles Winery & Vineyard for an evening of mouthwatering BBQ, live music, and great wine! Bam Bam’s BBQ, based in Stephens City, VA, is a competition BBQ team turned mobile food and catering sensation—known for traveling all over...
Blessing of the Harvest September 13, 2025 All are invited to join hands with us on Saturday, September 13th for our annual Blessing of the Harvest at James Charles Winery—a cherished European tradition. At 2 PM, Rev. Bjorn C. Lundberg from Sacred Heart Catholic Church in Winchester will bless the vineyard, asking for grace and...
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...
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...
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!...
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...
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...
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....