Saturday, February 28 • 12-6 PM Savor Spanish flavors and vineyard views at our second Paella Day. The Paella and Tapas Place food truck will be on-site, firing up sizzling pans of traditional paella and tasty tapas to enjoy with James Charles wines. As the aromas rise, settle in for live music, perfect for lingering...
Live Music with Chris Harasyn Saturday, February 28 | 2 PM – 5 PM Spend your Saturday afternoon at James Charles Winery with live music from local favorite Chris Harasyn and the flavors of Paella Day. Chris, a Winchester-based singer-songwriter, brings a heartfelt mix of original songs and classic covers with his smooth acoustic style...
Saturday, March 21 • 7–10 PMTickets: $22 Get ready for a night of laughs at James Charles Winery. Join us on Saturday, March 21 for a lively comedy show featuring headliner Lionel Harris with David Griffin as the feature comedian, presented by Funny Business Agency. Lionel Harris is an award-winning comedian and filmmaker known for...
James Charles Winery Friday, March 27 • 7–10 PMFree • Open to the Public Put your knowledge to the test and join us for Trivia Night at James Charles Winery & Vineyard! Hosted by Dan McDermott with Route 11 DJ, this lively evening promises friendly competition and PRIZES. Gather your team, grab a glass of...
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 Winery & Vineyard! Hosted by Dan McDermott with Route 11 DJ, this lively evening promises friendly competition and PRIZES. Gather your team, grab a glass...
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 Bean is a special way to spend time with Mom. Enjoy spring vineyard views, live music, and wine! This is a ticketed event with reserved...
VA250 Fireworks at James Charles Winery & Vineyard Friday, July 11 • Open to the Public Join us on Friday, July 11 for a special fireworks celebration at James Charles Winery & Vineyard. Originally planned as part of last November’s U.S. Marine Corps Birthday Ball, this long-anticipated display will finally light up the summer sky...
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....
