May 2025 Can't-Miss Events

May we suggest clearing your calendar? With warm breezes, longer days, and downtown streets buzzing with life, Winston-Salem shines brighter than ever in May. The city comes alive with music, food, art, and family fun—plus a few new events you’ll want to say you experienced. From longtime favorites like Gears & Guitars (pictured above) to exciting newcomers like the Dream Asia Food Fest, it’s a month you won’t want to miss. Here’s a look at 30+ events worth adding to your calendar.

May 1
Camel City Blues at Incendiary. Winston-Salem's favorite blues band, Camel City Blues, will play in the Coal Pit adjacent to Incendiary Brewing. The group blends Southern blues, classic rock, and R&B for a crowd-pleasing sound rooted in the blues. The event is free and runs from 6–9 p.m.

May 1 
Sunset Salutations - Community Yoga.  These free yoga classes occur on the first Thursday of the month from April to October in downtown's Bailey Park. Be sure to bring your yoga mat and water, wear comfortable clothes, and arrive a few minutes early to pick out a spot on the lawn. In the event of rain, the class will be relocated to the Wake Forest Biotech Atrium. The event begins at 6 p.m. 

May 1–3
Shepherd’s Center Used Book Sale. Book lovers, rejoice! The annual Shepherd’s Center Used Book Sale features thousands of titles in all genres, from hardback novels to paperbacks and more. Proceeds support programs for older adults through The Shepherd’s Center of Greater Winston-Salem. Admission and parking are free; books are individually priced. Held at the Winston-Salem Fairgrounds, 569 Fairgrounds Blvd (Gate 7). Hours are 9 a.m.–9 p.m. Thursday and Friday, and 8 a.m.–2 p.m. Saturday (half-price day).

May 2
NCMA Lakeside Concert: Sir Woman & Isaia Huron. Set against the serene backdrop of a spring-fed lake at NC Museum of Art, Winston-Salem (NCMA), the Lakeside Concert Series delivers a one-of-a-kind outdoor music experience featuring genre-blending pop and rock acts. The May show brings the soulful, gospel-infused funk of Sir Woman alongside the genre-bending, emotionally charged stylings of Isaia Huron. Tickets are $18 in advance and $23 at the door (plus tax/fees). 7 to 9 p.m. 

May 3
WS Symphony: Peter and The Wolf. Perfect for kids and families, this whimsical concert brings Prokofiev’s Peter and The Wolf to life with help from the Winston-Salem Symphony and the playful performers of the Really Inventive Stuff Theatre Company. The program also features Leopold Mozart’s “Toy” Symphony and Anatoly Lyadov’s The Mosquito. Adults $10, children $7. Held at Brendle Recital Hall on the Wake Forest campus from 11 a.m. to 12 p.m.

May 3
FUSE Makers Market. Hosted by the Metal Mavens, this one-day outdoor market showcases 49 artists and makers on the historic cobblestone grounds of NCMA Winston-Salem. Visitors can shop for handmade goods across a range of mediums, enjoy food trucks, and engage in hands-on experiences with local collaborators. Nearly half of the artists are local, with many participating for the first time. Free admission. The market runs rain or shine from 10 a.m. to 5 p.m. 

May 2
3rd Street Soundwaves. Get ready to dance in the streets at the inaugural 3rd Street Soundwaves, a new free outdoor concert series held in front of Kaleideum in downtown. The event will feature music from Somewhat Petty, a legendary Tom Petty tribute band. Food, beer, and wine will be available for purchase, and attendees can enjoy $5 museum admission as part of First Fridays at Kaleideum. Mark your calendar—West End Mambo takes the stage for the next concert on June 6. Both events will be from 6–9 p.m.

May 3
13th-annual Kentucky Derby Party. Don your Derby best and raise a mint julep in support of Trellis Supportive Care at this spirited fundraiser hosted by the Trellis Leadership Council. Held in Biotech Place in downtown's Innovation Quarter, the event features live music, festive food and drinks, a silent auction, and a live stream of the Kentucky Derby—all to support hospice care in our community. Tickets range from $50 to $125 depending on level; for details and ticket options. 4–7:30 p.m.

May 3–31 (Saturdays)
Bowman Gray Racing. The 77th season of racing at NASCAR’s legendary “Madhouse” rolls on each Saturday night in May, with four divisional races featured weekly: street stock, stadium stock, sportsman, and modified. May highlights include a 100-lap modified race (May 3), 50-lap street stock race (May 10), crash fest with a chain race and demolition derby (May 17), 100-lap sportsman race (May 24), and another 100-lap modified clash (May 31). Tickets are $12 for adults, $2 for kids ages 6–11, and free for children 5 and under. For tips on attending your first race, check out our Bowman Gray Racing Guide here. Gates open at 6 p.m., and races begin at 8 p.m.

May 6–11, 20–25
Winston-Salem Dash Baseball. The hometown Dash continue their 2025 season at award-winning Truist Stadium with two extended homestands in May. Game day promotions include Pups in the Park/Thirsty Thursday (May 8, 22), post-game fireworks (May 9–10, 23–24), and Sunday Fundays with a family ticket package of four tickets, hot dogs, chips, and drinks for just $60 (May 11, 25). Check the Dash website for full promotions, game times, and ticket info.

May 7, 8, 16
UNCSA Student Screenings. Get an inside look at the next generation of filmmakers during the annual student film screenings from the UNCSA School of Filmmaking. Third-year students present their inventive, university-funded short films on May 7–8, while graduating fourth-year students debut their professionally produced thesis films on May 16 (link). All screenings are at ACE Main Theatre on the UNCSA campus, 1533 S. Main Street. Admission is free. Showtimes are 7 p.m. on May 7–8, and 4 p.m. and 8 p.m. on May 16.

May 9
NC Fine Wines Awards Gala. Celebrate the best of North Carolina winemaking at this elegant gala held at downtown's Millennium Center. Enjoy a sparkling wine welcome, six award-winning wines paired with food, and the official unveiling of this year’s top bottles. It’s a night of sophistication, flavor, and fun in Winston-Salem, aka, the Gateway to Yadkin Valley Wine Country. Tickets start at $125. It will be held 6:45–10 p.m. 

May 10
NCMA 2nd Saturday: Family Art Activities. Create, explore, and get inspired during NCMA’s free Family Art Activities, held the second Saturday of each month from 11 a.m.–2 p.m. In May, families can make kinetic and mobile sculptures inspired by the Internal Review staff exhibition. That same morning, swing by Cars & Coffee from 9 a.m.–noon to see Italian cars on display. Admission to NCMA galleries is also free on second Saturdays—perfect for a full day of art, cars, and creativity.

May 10
SummerLark 2025: Old Crow Medicine Show. The third annual SummerLark concert returns to downtown's Bailey Park with a headline performance by Old Crow Medicine Show, the Grammy-winning Americana band known for their breakout hit “Wagon Wheel” and high-energy live shows. Hosted by Atrium Health Wake Forest Baptist, this benefit event supports the Cancer Patient Support Program. Enjoy an evening of music, food trucks, a free photo booth, and more. Ticket prices start at $47.50. 7–11:30 p.m.

May 10
Kaleideum After Dark: Gear Up! Enjoy a night of creativity and grown-up fun at Kaleideum’s monthly After Dark series. May’s edition teams up with Gears & Guitars for a night of bike-inspired fun, featuring hands-on activities, food trucks, and rooftop live music from throwback cover band High School Reunion. Tickets are $20 in advance, $25 at the door, and include two drink vouchers. 6:30–9:30 p.m.

May 10, 11
WS Symphony finale: Titan. In a stirring season finale, the Winston-Salem Symphony presents a dynamic pairing of Sarah Kirkland Snider’s haunting Something for the Dark with Mahler’s sweeping Symphony No. 1 in D minor, known as “Titan.” Conductor Michelle Merrill leads this emotional concert journey through light, darkness, despair, and triumph. Held at R.J. Reynolds Auditorium, 301 North Main Street. Tickets start at $25. Saturday at 7:30 p.m. and Sunday at 3 p.m.

May 13
Dino Dig at Washington Park. Little explorers are invited to Washington Park’s Dinosaur Playground for the annual Dino Dig, a free event hosted by Winston-Salem Parks & Rec. Kids can hunt for dino “fossils,” bones, and other fun surprises, then enjoy a themed craft activity. 10–11 a.m.
 

May 16
Art Crush 2025. The Downtown Arts District’s signature block party is held on the third Friday of each month from April to December. Enjoy street vendors, live entertainment, kids’ activities, extended gallery hours, and shopping for handmade art—all centered around the lively intersection of Sixth and Trade Streets. 7–10 p.m.

May 16
Innovation in Cinema Series: Pitch Perfect. Downtown’s monthly outdoor movie series continues with the 2012 musical comedy Pitch Perfect. Screenings are free and held at Bailey Park in the Innovation Quarter. Pets are welcome but must be leashed. Food and beverages will be available for purchase starting at 7 p.m., with the movie beginning at sunset.

May 16
Starlight Movie Night in Lewisville: Twisters. The Town of Lewisville kicks off its 2025 Starlight Movie Night series with the action-packed 2024 blockbuster Twisters, shown under the stars at Shallowford Square, 6555 Shallowford Road. Admission is free—just bring a lawn chair or blanket. Concessions will be available, and coolers are welcome, but pets and alcohol are not permitted. Pre-movie activities start around 8 p.m., with the film beginning at dark. 

May 16-18
Winston-Salem Greek Festival. Opa! The Winston-Salem Greek Festival returns with three days of mouthwatering cuisine, live music, cultural exhibits, church tours, shopping, and family fun. Held at the Annunciation Greek Orthodox Church, the festival features everything from souvlaki and spanakopita to handmade Greek jewelry and a bustling marketplace. Kids can enjoy games, treats, and more. Admission is $6 for adults and free for children 12 and under, with proceeds benefiting Cancer Services. Festival hours are 10 a.m.–10 p.m. Friday–Saturday, and 11 a.m.–8 p.m. Sunday.
 

May 17
MESStival at Kaleideum. Get ready to dive into gooey, slimy fun at Kaleideum’s annual MESStival, a hands-on celebration of science and art for the whole family. From foot painting to water play and a Rockstar Bubbles Foam Party, this all-day event encourages kids (and grown-ups) to get messy while learning through play. Activities take place inside the museum and outside in Liberty Plaza. Dress for mess and bring a towel and change of clothes. Included with regular admission or membership; tickets are $10 in advance, or $15 at the door. 10 a.m.–5 p.m. 

May 17–18
Dream Asia Food Fest. The largest Asian food fest in the U.S. comes to the Winston-Salem Fairgrounds with 90+ vendors, including 30+ buzzworthy pop-ups from NYC. Enjoy two full days of street food, cultural performances (like K-pop, lion dances, and more), shopping at a bustling bazaar, and hands-on workshops for all ages. Tickets are $12/adults, and free for kids 10 and under. 12–10 p.m. 

May 23
Fairgrounds Concert Series: Rodney Atkins with Hunter Hayes. The annual Fairgrounds Summer Concert Series kicks off at the Winston-Salem Fairgrounds Arena with two country-music stars. Rodney Atkins is a chart-topping artist known for heartland anthems like “Take a Back Road” and “If You’re Going Through Hell.” Meanwhile, Hayes is a polished country-pop musician known for his chart-topping hit “Wanted.” Tickets start at $42. 7 p.m.

May 23–24
Gears & Guitars 2025. Billed as “the biggest party on two wheels,” Gears & Guitars brings pro racing, community rides, and free live music to downtown Winston-Salem each Memorial Day Weekend. Friday night kicks off with the crowd-favorite Streets of Fire sprint race and music on Fourth Street, while Saturday’s all-day events unfold in the Innovation Quarter with Fondo rides, criterium racing, food trucks, a beer garden, and big-name concerts at Bailey Park. Full schedule and lineup are coming soon.

May 24
Fairgrounds Concert: Stokley ft. Chanté Moore. R&B powerhouses Stokley—Grammy-nominated frontman of Mint Condition known for “She”—and Chanté Moore, famed for sultry ‘90s hits like “Chanté’s Got a Man,” take the stage for a soulful night at the Winston-Salem Fairgrounds Arena. Special guests Envision open the show. Tickets start at $36. 7 p.m.

May 25
Winston-Salem Food Truck Festival. 1–7 p.m. Winston-Salem's biannual food truck festival returns to the downtown's Industry Hill neighborhood, as dozens of food trucks will line up along Ninth Street between Wise Man and Radar Brewing. There will also be live music, craft beer, kids activities, and more. Admission is free. 1–7 p.m.

May 27
Salem Band Concert with Paperhand Puppet Intervention. The nation’s oldest mixed wind ensemble kicks off its summer season with a crowd favorite: a magical, family-friendly performance alongside the acclaimed Paperhand Puppet Intervention. Enjoy music from Encanto, Pirates of the Caribbean, and more in historic Salem Square. Bring a blanket or lawn chair; food trucks will be on-site, or pack a picnic. Pre-concert activities begin at 6:45 p.m., and the free concert starts at 7:30 p.m.

THROUGHOUT THE MONTH

May Concerts at The Ramkat. Downtown’s premier music venue hosts a strong lineup of regional and national acts this May. Highlights include Americana duo Gillian Welch & David Rawlings (May 1), pop-violinist Kishi Bashi (May 2), gritty folk favorite Amigo the Devil (May 3), Phish tribute Runaway Gin (May 8), country star Sara Evans (May 10), Guns N’ Roses tribute Nightrain (May 15), North Carolina pop-rockers The Connells (May 17), Americana favorites American Aquarium (May 30), and Allman Brothers tribute End of the Line (May 31). Additional performances will take place in both the main hall and the more intimate Gas Hill Drinking Room.

David LaChapelle + Internal Review: Exhibits at NCMA. NC Museum of Art, Winston-Salem (NCMA) features two standout exhibits this month. David LaChapelle: Dear Sonja is a powerful retrospective of the internationally acclaimed photographer and UNCSA alum, on view through July 20. Through May 18, Internal Review showcases the creative work of NCMA staff across diverse mediums. Both exhibits are included with museum admission: $8 adults, $6 students, seniors, and military; free for kids 17 and under.

Taste of Art classes at Sawtooth. These popular one-night workshops let guests spend a few hours creating art to take home. Multiple classes are scheduled every Friday in May, all taught by local artists, and several Saturday workshops are also planned. Most Taste of Art classes are held at the Sawtooth School downtown (251 N. Spruce Street), though some weekday classes are at Sawtooth's secondary studio at The Generations Center (114 W. 30th Street). Classes are held in various mediums including glass, ceramics, jewelry, fibers, and more.

Reynolda Exhibit: Andrew Wyeth at Kuerner Farm. This is the final month to see this dazzling spring exhibit at Reynolda House Museum of American Art. On display until May 25, the exhibit highlights rare works from one of the most popular American artists of the 20th century, Andrew Wyeth. Admission is included with entrance to Reynolda; $18 adults; free from children, college students, teachers, veterans, and more. In addition, Reynolda has a number of special events happening this month to complement the exhibit, including a special Curator Talk with Allison Slaby, curator at Reynolda, on May 17. 

 
Want more May events?  Check out our Events Calendar to see dozens more local happenings this month.