Winston-Salem’s Top Twelve Wine-Country Escapes

The Living in Winston-Salem Events Page focuses on events at these twelve vineyards and wineries. If you’re a wino, be sure to subscribe to our newsletter. We’ll keep you updated as we continue to add content on the area’s best vineyards and wineries. With around 200 wineries and 400 vineyards across the state, North Carolina ranks 10th […]
RAYLEN: Hallowine Pumpkin Carving Festival
Event Details: Join Raylen for an annual Hallo-Wine pumpkin carving festival from 5:00-9:00pm! Dress in your best Halloween costume and enjoy an evening of pumpkin carving, live music, and delicious food! Live music by SoundKraft and food for purchase from West Coast Wanderer. Sweet treats and specialty drinks will also be available from Sweet Magnolia Mercantile. Pumpkins are $10 […]
RAYLEN: Fall Market
Event Details Usher in the Fall season with Raylen’s Annual Fall Market – the biggest one yet! Shop local and support some of the area’s best vendors. Market hours: 11am-5pm. There will be live music by Darrel Hoots and food for purchase from JJ’s Cuban Kitchen, El Taco Vaquero, Victory Donuts, Patriot Pretzel, and Old South Kettle Corn from noon-4pm. Interested in […]
RAYLEN: Jazz Sunday
Event Details Spend a relaxing Sunday afternoon at the vineyard listening to the smooth jazz sounds of Red Umber Food for purchase from Wanderlust Boards and Sol Kitchen from 1:00pm-4:00pm! You can pre-order a charcuterie board by clicking HERE. Music is complimentary and open to the public. Feel free to bring a lawn chair! No outside alcohol, food, balls, scooters, […]
RAYLEN: Fall Cornhole Tournament
Event Details Raylen’s Annual Cornhole Tournament in partnership with the Gilliland Foundation to benefit children battling cancer. A fun-filled day of live music, food trucks, wine, and more! Tournament Details: -Two-Person Double Elimination -48 team slots available -$50 registration fee per team -Check-in begins at 11am -Games start at 12pm Entertainment Details: -Food Trucks: Kaveman Dogs & Mom Boss […]
RAYLEN: Friday Night Live
Event Details: Live music by Red Umber and food available for purchase by Agueybana El Bravo. Music is complimentary and open to the public. Feel free to bring a lawn chair! No outside alcohol, coolers, balls, scooters, or bicycles. Rain or shine.
Giggles & Glasses Comedy Night at Raylen
Join us for an evening filled with laughter and good times at RayLen Vineyards! We are excited to present a Comedy Night featuring the hilarious comedian Derrick Knopsnyder and his friends from the Uncorked Comedy Tour. Get ready for an evening of side-splitting jokes and witty humor that will leave you in stitches! Date: July 13th, 2023 […]