Live Music with Nate Hadley Saturday, July 19 | 3–6 PM James Charles Winery & Vineyard Join us for an afternoon of wine and live music with Nate Hadley, a Winchester-based folk-Americana artist known for his rich acoustic sound and heartfelt lyrics. Drawing inspiration from artists like Tyler Childers and The Lumineers, Nate blends modern...
🎶 Live Music with Rachel Brinkmeier at James CharlesThursday, July 25 | 7–10 PM Join us for a magical summer night at James Charles Winery with live music from the incredibly talented Rachel Brinkmeier, performing from 7 to 10 PM! Known for her soulful voice and acoustic storytelling, Rachel brings a blend of heartfelt originals...
Friday, July 25 | 8–11 PMLive Music by Rachel Brinkmeier | 7–10 PM Join us at James Charles Winery for a magical summer night of wine, live music, and stargazing during the Delta Aquarids meteor shower—a perfect excuse to slow down and look up. Bring the family, spread out on the lawn, or watch from...
🎤 Live Music with Austin NemithSaturday, July 26 | 3–6 PMJames Charles Winery & Vineyard Join us for a soulful afternoon as Austin Nemith brings his authentic Americana sound to the vineyard. A West Virginia native with deep roots in folk, country, bluegrass, and funk, Austin delivers passionate original songs and crowd-pleasing covers that resonate...
Saturday, August 2, 2025 | Noon – 7 | James Charles Winery & Vineyard Cousins Maine Lobster Food Truck is rolling into James Charles Winery & Vineyard for a day of fresh, mouthwatering seafood! Indulge in Maine-style lobster rolls, creamy bisque, flavorful tacos, and more, all perfectly paired with your favorite award-winning wines.
Live Music with Rain Mayo📅 Saturday, August 2 | 🕒 3 PM – 6 PM📍 James Charles Winery & Vineyard Join us for an afternoon of wine and music as Rain Mayo takes the stage at James Charles Winery. Known for her rich vocals and soulful acoustic style, Rain blends indie, folk, and pop influences...
Live Music with Chris Harasyn📅 Saturday, August 9 | 🕒 3 PM – 6 PM📍 James Charles Winery & Vineyard Spend your Saturday afternoon at James Charles Winery with live music from local favorite, Chris Harasyn. A Winchester-based singer-songwriter, Chris brings a heartfelt mix of original tunes and classic covers with smooth acoustic style and...
🐾 Yappy Hour at James Charles WineryFriday, August 15 | 4–7 PM Back by pup-ular demand—with an extra hour added so you can make it after work! Join us for our next Yappy Hour, where dogs and their humans come together for wine, treats, and tail-wagging fun. Whether you're stopping by for the first time...
Potato Sensations at Yappy Hour – Friday, August 15 | 4–7 PM 🥔 Join us at James Charles Winery for Yappy Hour and treat yourself to the ultimate comfort food from Potato Sensations! They’ll be serving up perfectly baked potatoes, crispy seasoned fries, and mouthwatering loaded creations like The Cajun Way, Loaded BBQ, and The...
Live Music with Lex Sacco📅 Friday, August 15 | 🕒 4–7 PM📍 James Charles Winery & Vineyard Spend your Friday evening with the unforgettable voice of Lex Sacco, a powerful and emotive performer whose music blends roots rock, country, and pop influences. Known for her rich vocals and expressive songwriting, Lex delivers both original songs...
🎶 Live Music with Nate HadleySaturday, August 23 | 3–6 PMJames Charles Winery Spend your Saturday afternoon in the vines with the acoustic sounds of Nate Hadley, a Winchester-based folk-Americana artist. Known for his rich, heartfelt vocals and rootsy storytelling, Nate draws inspiration from artists like The Lumineers and Tyler Childers. His warm, honest sound...
Saturday, September 6, 2025 | Noon – 7 | James Charles Winery & Vineyard Cousins Maine Lobster Food Truck is rolling into James Charles Winery & Vineyard for a day of fresh, mouthwatering seafood! Indulge in Maine-style lobster rolls, creamy bisque, flavorful tacos, and more, all perfectly paired with your favorite award-winning wines.