Events

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...

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...

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...

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...