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 | 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 originals and beloved covers spanning country, pop, and rock, into a captivating set that pairs beautifully with a glass of wine. Free to attend!

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...

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...

Blessing of the Harvest September 19, 2026 All are invited to join hands with us on Saturday, September 19th 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 a bountiful harvest....

Now hear this! Now hear this! James Charles Bogaty, a US Marine and this winery’s namesake, invites you to celebrate the 251st birthday of the Marine Corps! Please join us on Saturday, 14 November 2026 from 1800-2300 (6:00-11:00 PM). This event is open to United States Marines, past or present, and their guests. A social...