Events

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!

1776 Wine Sale🍷July 4-5, 2026 James Charles Winery is celebrating America’s 250th birthday with a special 1776 Wine Sale. For two days only, our James Charles Riesling will be just $17.76. Come out over the Fourth of July weekend and spend some time with us. Riesling is a great bottle to bring home for summer,...

VA250 Fireworks at James Charles Winery & Vineyard Friday, July 11 • Open to the Public - Rain Date TBD Join us on Saturday, July 11 for a special all-day fireworks celebration at James Charles Winery & Vineyard, proudly sponsored by the Marine Corps League LT General Lewis Puller Department. Originally planned as part of...

Fizzle's BBQ will be joining us at James Charles Winery xon Saturday, July 11, during our VA250 Fireworks celebration. Come early, grab a glass of wine, and enjoy local BBQ while spending the day with us before the fireworks light up the summer sky. The tasting room opens at 12 PM, and guests are encouraged...