Before you head to the Winston-Salem Greek Festival, be sure to check out the entertainment lineup. | Photo courtesy of The Greek Festival
These are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
Foodie favorites
2025 NC Fine Wines Awards Gala | Friday, May 9 | 6:45-10 p.m. | Millennium Event Center | $200 | Start your evening with food and wine pairings + learn more about some of the best local wineries.
Winston-Salem Greek Festival | Friday, May 16-Sunday, May 18 | Times vary | Annunciation Greek Orthodox Church | $5 | Savor Greek dishes as you watch live music and dance performances + shop the marketplace.
Gear up for a little competition in May.
Photo courtesy of Gears & Guitars
Festivals + fairs
May Day Market and Festival | Sunday, May 4 | 1-6 p.m. | Brouwerij DuBois | Cost of purchase | Celebrate planting season with a vendor market, live music, food by Smoke Revival Meat Company, and seasonal taps.
Gears and Guitars Festival 2025 | Friday, May 23-Saturday, May 24 | Times vary | Bailey Park | Free | Combine live music + cycling, and you’ve got one of the country’s most prestigious cycling events.
Shannon Curtis: “‘80s Kids” | 8 p.m. | The Ramkat | $28+ | The show combines some of the biggest hits from the decade into one show — think: John Hughes movie soundtracks.
Wednesday, April 30
Charles Krypell Spring Trunk Show | Wednesday, April 30-Thursday, May 1 | Times vary | Windsor Jewelers | Cost of purchase | Meet Charles in person as he helps you choose a piece from the latest collections — refreshments will be provided.
Thursday, May 1
38th Annual Shepherd’s Center Used Book Sale | Thursday, May 1-Saturday, May 3 | Times vary | Winston-Salem Fairgrounds | Cost of purchase | Start adding to that “to-be-read” pile by shopping thousands of used books for sale.
Friday, May 2
“Charlie and the Chocolate Factory” | Friday, May 2-Sunday, May 4 | Times vary | Winston-Salem Theatre Alliance | $19+ | Enter a world of pure imagination when you watch this tasty Broadway and West End musical based on the famous novel and hit movie.
Saturday, May 3
Tequila Tasting | 2:30-4 p.m. | Alma Mexicana | $25 | The restaurant will talk about its house tequila, El Jimador, while guests taste pours of three types of the liquor.
Tickets are still available for this one-night-only concert in Bailey Park, presented by Allegacy Federal Credit Union. All proceeds support Atrium Health Wake Forest Baptist’s Cancer Patient Support Program.
ICYMI, here’s what to expect at this year’s festival:
An opening act by Big Daddy Love, an “Appalachian Rock” quartet founded by Sparta and Winston-Salem natives.
Grammy-winning headliners Old Crow Medicine Show
Food trucks, a free photo booth + family-friendly fun
Winston-Salem software company Troodie is one of two state startups to receive funding from NC Idea. The $10,000 grant is intended to advance companies’ objectives + includes an eight-week customer discovery and product launch program. (Winston-Salem Journal)
Ranked
The UNCSA School of Filmmaking has done it again. It’s landed on Variety’s list of top film schools for the 10th consecutive year, with the publication noting the school’s “ability to prepare students for a variety of careers.” See for yourself — graduating seniors will present over a dozen free screenings next month.
Shop
Shop ‘til ya drop — after hours. City Beverage is hosting an outdoor night market from 5 to 8 p.m. on the second and fourth Wednesday of every month. Through October, browse a variety of food and artisan vendors in the parking lot. (Winston-Salem Journal)
Learn
T-minus two days until registration for the Vecino Center’s summer intensive courses opens. Classes meet three times weekly for two weeks, beginning at 6 p.m. Bookmark the website tab so you can browse for the course that suits you.
Eat
Satisfy your weekend brunch cravings with this easy chicken and waffles recipe. Hint: It transforms the classic combination into a deliciously satisfying one-pan casserole, which pairs perfectly with a drizzle of hot honey. Get cooking.*
The car tech upgrades you need ahead of summer road trips for better, safer driving:
🗺️ No more phone in your cup holder — keep navigation instructions in your eyeline with a suction cup phone mount equipped with one-button release.
🔊 Skip plugging in your phone to activate CarPlay and use this wireless CarPlay adapter for a faster, more reliable bluetooth connection.
🚙 A front and rear dash cam can make all the difference in a fender bender — this one captures crystal-clear footage even at night.
📲 Everyone gets to charge their devices at once with a four-port car charger that’s here to end road trip squabbles.
🌸 Looking for an air freshener upgrade? This No. 1 best-selling wood air freshener looks chic on your sun visor.
Hey Winston-Salem. 👋 I’m just popping in to say hello as I help Kellina out this morning.
But while I have you, I wanted to (respectfully) point out OpenTable’s oversight. If you were reading the reservation platform’s “Top 100 Brunch Restaurants,” you’ll notice the Twin City’s absence. What about one of these 20+ egg-cellent options?
Hey [First Name], I wanted to personally send you this quick note. I hope you're doing well! Let me know if you have any thoughts on this. Feel free to reply, and we can chat more. Looking forward to hearing from you soon.
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