A MESSAGE FROM 500 W 5TH
Chef's Kiss Dining
5 reasons to dine at The Downtown Grille this spring!
The Vibe: Sun-drenched windows, an intimate dining room, and a plant-filled patio with couches for cocktails and apps and tables when you're ready for the full experience.
Locally Rooted: Nearby farms supply the kitchen, local distilleries stock the bar, and every dollar spent strengthens the community.
The Chef: Creativity and consistency on each plate, a combination that's hard to find. Stay tuned: their summer menu comes out next week.
Drinks Done Right: Crafted cocktails and mocktails that are genuinely chef's kiss. Their new cocktail menu just dropped. We are eyeing the "Fresh Out The Slammer."
Daily Specials: Deals run all day, every day. Think $12 crafted cocktails every Friday and $5 off Chef-Selected Appetizers every Tuesday.
Go ahead and make your reservation!
📅 Mark Your Calendar
From The Fray live in concert to the annual Greek Festival, May has something for everyone to enjoy!
Winston-Salem Greek Festival
Music & Entertainment
SummerLark | May 9 | Bailey Park | The Fray takes the stage for this year’s benefit concert supporting Atrium Health's Cancer Patient Support Program. We already have “How to Save a Life” stuck in our heads.
Defying Gravity | May 9 | Reynolds Auditorium | No need to travel over the rainbow. The Winston-Salem Symphony performs your favorite tunes from “The Wizard of Oz,” “The Wiz,” and “Wicked”!
Gears & Guitars | May 22 & 23 | Downtown | Watch high-speed cycling races and jam out at 7 free concerts, featuring local acts and headliner Saint Motel!
Music & Puppets | May 26 | Salem Square | Giant puppets and your favorite movie soundtracks? Paperhand Puppet Project and Salem Band team up for a magical performance!
Interactive
Cardboard Boat Regatta | May 9 | Winston Lake Park | Cheer on the brave captains racing homemade cardboard boats across the lake!
Greek Festival | May 15-17 | Annunciation Greek Orthodox Church | Dive into a Greek cultural experience! Savor authentic dishes, watch traditional dances, and tour the magnificent church. Opa!
Food & Shopping
Hope du Jour | May 5 | Various establishments | Dine out and give back. Over 100 local restaurants will donate 10% of proceeds to Crisis Control Ministry. It's a delicious way to make a difference.
Used Book Sale | May 7-9 | WS Fairgrounds | Stock up on your summer reading for a steal (and a good cause)! Proceeds benefit The Shepherd's Center, a nonprofit providing services and enrichment programs for older adults.
Food Truck Festival | May 24 | E. 9th Street | With 12+ food trucks to choose from, the only problem you'll have is deciding where to start!
Three types of workers you will meet at Flywheel Coworking:
Entrepreneur/Business Owners | From legal professionals to creatives, Flywheel attracts a diverse range of business owners — like Miller C.
Remote Workers | Industries of all kinds call Flywheel home, from education and finance to marketing and law — like Donny W.
Small Teams | Small companies of 2-3 people to large teams of 10, like The Go-To Winston-Salem (oh hey).
Ready to find your people? Check out Flywheel's flexible memberships and find your perfect coworking spot!*
🗓 Events
Saturday, May 2
Johnny Loves Johann - Bach, reimagined. Experience the music of Bach performed by a GRAMMY-winning violinist alongside a breathtaking dance performance at Agnes de Mille Theatre. Additional performance on Sunday.*
Community Day - Face painting, scavenger hunts, disc golf tournaments, and more — don’t miss Lewisville’s first-ever community day! Free breakfast and lunch included. 10 AM - 2 PM
Petals & Pints - Cross off your Mother's Day shopping list. Browse 15+ vendors and grab a plate of BBQ at Radar Brewing! 1-6 PM
The Wizard of Oz - Watch the classic movie at Tanglewood Park for free; arrive early for a Dash City Saxophone Quartet performance! Movie starts at sundown.
Brookstown Block Party - Browse art vendors and grab a bite from food trucks at Cotton Street Apparel! 12-5 PM
Sunday, May 3
Rescue for the Roses - This Derby-themed fundraiser at Medaloni Cellars features Uptown Dueling Pianos, a silent auction, and lawn games! Proceeds support Red Feather Equine Sanctuary. 12 PM
Trade Street Farmers Market - Taste the difference. Support your local producers by shopping fresh fruit and veggies, baked goods, and more on Trade Street! 10 AM - 2 PM
May Day Festival - Celebrate spring with face painting, flower crowns, live music, and a vendor market at Brouwerij DuBois! 12-8 PM
Line Dance Party - Pick up a new routine with Maggie Shipley, then hit the floor for open dancing! 12:30-4:30 PM
Embroidery 101 - Learn the basics of embroidery and stitch a dandelion at Village Fabric Shop! Supplies included. 4 PM
Monday, May 4
Trivia Night - May the 4th be with you. Show off your Star Wars knowledge in Wise Man Brewing’s themed trivia night! 7:30 PM
DIY Cards - Handmade is better. Learn to craft a beautiful card at the Generations Center — just in time for Mother's Day! 1 PM
🗞 Other News
💪 Strength: The power duo you didn't know you needed. Emsella + Emsculpt NEO work together to strengthen your pelvic floor and sculpt your core with no downtime. Feel strong & confident this summer!*
🍊 Opening: The Jugo Bar opens at 411 W. 4th Street this Friday! Created by local William Fulton, this juice bar will serve cold-pressed juices, smoothies, smoothie bowls, mushroom coffee, and rooibos tea.
🎓 University: Forsyth Tech is one of 25 semifinalists for the 2027 Aspen Prize, the nation’s most prestigious community college award! Finalists will be announced in June, with the $1 million prize winner revealed in April 2027.
🏆 Ranking: JOLO Winery’s End Posts Restaurant made OpenTable’s Top 100 Brunch Restaurants! Check out our brunch guide for even more great brunch spots.
📖 Save the Date: Two-time Pulitzer Prize winner Colson Whitehead is coming to town on July 30! Whitehead will discuss his new novel, “Cool Machine,” live at First Baptist Church. Grab your tickets before they're gone!
🍨 Star Wars: Come to the dark side, we have ice cream. Twin City Sweets’ Star Wars-themed weekend kicks off this Friday! Expect character cutouts, animatronics, and themed sundaes like the “Mintlennium Falcon.”
🧸 Kids: Kaleideum opens the first-ever “Doc McStuffins” children's museum exhibit this Saturday! Kids will dive into imaginative play at the McStuffins Toy Hospital while learning about health and wellness.
👀 Poll results:
All the time - 33%
Occasionally - 49%
Never - 18%
Madison A. listens to music all the time and shared, “I stay focused better if I’m listening to my favorite songs. Plus, it drowns out the silence of looking at a computer screen all day.”
SPONSORED
Upcoming Events
Community Gathering - One of America's most celebrated poets is coming to town! Join the Winston-Salem Foundation for a social hour, hands-on activity, and keynote from poet Ada Limón at the Benton Convention Center on May 18.
🌀 The Wrap
😅 Our bad. Kayak rentals at Salem Lake won't be available May 1 as we mentioned in last night’s newsletter.
🎉 Happy birthday to team member Bre! We have a bittersweet update: Bre will be moving away after she gets married this summer. We've absolutely loved having her on the team and are so grateful for the joy she brought us. Wishing her all the best in this exciting new chapter!
THANK YOU TO OUR PARTNERS
* denotes sponsored content