Events

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...

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 a chance to spin the wheel and unlock a special food or drink offer, along with a few surprises. Bring your friends, grab a glass,...

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...

Join us at James Charles Winery & Vineyard on Saturday, July 11, for an evening of live music with John D. Neal during our VA250 Fireworks celebration. An independent American singer-songwriter and recording artist, John D. Neal blends country, gospel, and blues into a vintage Americana sound that feels perfectly suited for a summer evening...

Join us on Friday, July 17 for an exclusive Pre-Release Tasting for James Charles Winery Club Members. Enjoy an early tasting of 2024 Bogaty Reserve Malbec and 2025 JB Vidal Blanc before their official release. Our winemaker will speak about each wine and offer insight into the craftsmanship and story behind the releases. Tasting times:7:00...

Join us for Yappy Hour at James Charles Winery & Vineyard on Friday, September 11, 2026, from 4–7 PM with live music by Lindsay Beth Harper. Lindsay Beth Harper is a Nashville-based country singer-songwriter from the Blue Ridge Mountains of Georgia, known for blending traditional and modern country sounds with heartfelt lyrics and rich vocals....

Join us for Yappy Hour at James Charles Winery & Vineyard on Friday, September 11, 2026, from 4–7 PM with food from Franklin’s Smokin Barnyard. Born from a backyard passion for barbecue, Franklin’s Smokin Barnyard serves up mouthwatering smoked meats and BBQ favorites made to bring people together. It’s the perfect tail-gate pairing: wine in...

Back for a second year! Join us for Yappy Hour: Tail-Gate at James Charles Winery on Friday, September 11, 2026, from 4-7 PM. Bring your pup and enjoy an evening of $7 glasses of wine, free dog treats, local vendors, a dog photo booth, live music from country artist Lindsay Beth Harper, and a food...