Events

Join us at James Charles Winery on Saturday, April 18 for live music with Dan Cronin, also known as Panhandle Dan. A fingerpickin’ enthusiast with a lively, roots-inspired style, Dan...

James Charles Winery Friday, April 24 • 7–10 PM Free • Open to the Public Put your knowledge to the test and join us for Trivia Night at James Charles...

Empanadas & Wine Pairing Join us on Saturday, April 25th for a special Empanadas & Wine Pairing experience at James Charles Winery. This ticketed event features three limited seating times...

Saturday, May 9th at James Charles Winery Tickets Here: $45 per person Celebrate Mother’s Day weekend with a sweet afternoon! Our Cheesecake & Wine Pairing ft. gourmet cheesecake from Cheesecake...

Join us at James Charles Winery on Saturday, May 9 from 3 PM to 6 PM for live music with Brent Kimbrough during our Mother’s Day Cheesecake Pairing event. Brent...

Saturday, May 23 • 12-7 PM Savor Spanish flavors and vineyard views at our third Paella Day. The Paella and Tapas Place food truck will be on-site, firing up sizzling...

Saturday, May 23 | 3–6 PM Join us for a relaxed afternoon as Rachel Brinkmeier brings her soulful acoustic vibe to James Charles Winery. With two decades of experience, Rachel blends heartfelt...

James Charles club members are invited to join us for a club-exclusive pickup party. Pick up your June club order in person, enjoy complimentary appetizers, and spend the evening at...

Join us at James Charles Winery & Vineyard on Saturday, June 6, from 3–6 PM for live music with Ethan Harrison Smith. Ethan is an American folk singer/songwriter and performing...

Your Friday plans just got better! 🎡🍷 Join us every Friday from 4-6 PM, beginning June 12 through September 25, 2026, for Spin & Sip Happy Hour. Each guest gets...

Join us for Corks & Cakes, a delicious bundt cake and wine pairing experience at James Charles Winery. We’re excited to feature Nothing Bundt Cakes from their newest Winchester location for this sweet and celebratory pairing experience. Guests will enjoy four mini bundt cake flavors, each thoughtfully paired with a James Charles wine. The pairing...

Saturday, June 20 | 3 PM – 6 PM Spend your Saturday afternoon at James Charles Winery with live music from local favorite Chris Harasyn. Chris, a Winchester-based singer-songwriter, brings a heartfelt mix of original songs and classic covers with his smooth acoustic style and soulful vocals. Free to attend!