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...
Glow in the Dark Easter Egg Hunt (Adults Only) Friday, April 3 | 6–9 PMHunt begins at 7:30 PMTickets: $25 | 21+ only James Charles Winery & Vineyard is putting a grown-up twist on a classic tradition with our first-ever Glow in the Dark Easter Egg Hunt—a 21+ ticketed event designed to be completely different...
Enjoy live music from Alex Kerns at James Charles Winery & Vineyard during our Glow in the Dark Easter Egg Hunt on Friday, April 3rd, from 6–9 PM. Born in Winchester and raised in Berryville, Alex is a Shenandoah Valley favorite. His sound blends folk-Americana originals with influences ranging from The Beatles and Jack Johnson...
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 brings the kind of music that feels right at home in a winery setting. With guitar and harmonica, he delivers the infectious sounds of ragtime...
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...
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 at 1 PM, 2 PM, and 4 PM, with just 10 spots available per time slot. Tickets are $25 per person. We’re excited to partner...
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...
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 Kimbrough is a talented guitarist known for his versatile style shaped by jazz, blues, classical, and country influences. His rich sound and years of performance...
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 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...
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!
