May 2026 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 to the return of Art Crush, it’s a month you won’t want to miss. 

May 1
Pictures at an Exhibition (with Film). 7:30 p.m. The Piedmont Wind Symphony — an ensemble of the region's top wind musicians — present this uniquely immersive concert experience at Brendle Recital Hall on the Wake Forest campus. Modest Mussorgsky’s "Pictures at an Exhibition" is brought to life with film, transforming this beloved work into a multi-sensory journey. The concert also features Gala Flagello’s virtuosic "The Bird-While," blending vivid soundscapes with storytelling. Tickets are $27-$64,

May 2
Derby Day at Wise Man: “The Grateful Derby.” Wise Man Brewing puts a jam-band spin on the Kentucky Derby with a two-part celebration: Derby by day, Dead by night. Catch the race on big screens, browse a vintage market (12–7 p.m.), and create your own look at the brimmed hat bar. Then stick around for live music, with afternoon jam sets followed by a Jerry Garcia tribute band in the evening. Admission is free.

May 3
Trade Street Farmers Market. 10 a.m.–2 p.m. The Arts District’s monthly market returns, bringing more than 30 regional vendors to Trade Street between 5th and 6th. Shop fresh produce, flowers, baked goods, and prepared foods while enjoying live music and a laid-back Sunday vibe. Admission is free. For updates and vendor info, visit the market’s Facebook page (link).

May 3
14th-annual Kentucky Derby Party. 4–7 p.m. Don your Derby best and raise a mint julep in support of Trellis Supportive Care at this spirited fundraiser in downtown's Robert Hall. Enjoy live music, festive food and drinks, a silent auction, and a live stream of the Kentucky Derby—all to support hospice care. Tickets are $85 and include drink tickets; VIP admission is $150 and includes open bar and a mint julep.

May 7
Sunset Salutations - Community Yoga.  Led by 2B Yoga, these free yoga classes occur on the first Thursday of the month from spring to fall 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. NOTE: Physical activity release waivers are required for each session. Complete the waiver in advance here or come early to fill it out in person.

May 7-9
Shepherd’s Center Used Book Sale. 9 a.m.–9 p.m. Held at the Winston-Salem Fairgrounds, this beloved annual event features thousands of titles in all genres, from hardback novels to paperbacks and more. Proceeds support programs for older adults in the community. Admission and parking are free; books are individually priced.  Saturday hours will be 8 a.m.–2 p.m. Saturday (half-price day).

May 9
WS Symphony: Defying Gravity: Music of OZ. 7:30 p.m. The Winston-Salem Symphony and conductor Michelle Merrill bring the epic songs from the wonderful world of OZ to life in this visual POPS concert. Dance down the yellow brick road with music from The Wizard of OZ, The Wiz, and Wicked. Held at Reynolds Auditorium, 301 N. Hawthorne Road. Tickets start at $30. 

May 9
Vegan Seafood Pop-up at Radar Brewing. 12–4 p.m. The popular plant-based takeover returns to downtown, serving up 100% vegan twists on nostalgic coastal classics. Come "sea" for yourself as Radar Brewing hosts a full menu of creative, animal-free seafood platters and loaded sides. It’s the perfect spot to grab a pint and enjoy a unique Saturday lunch. Admission is free

May 9
SummerLark 2026: The Fray. 7 p.m. The fourth annual SummerLark concert returns to downtown's Bailey Park with a headline performance by chart-topping rock band, The Fray. Hosted by Atrium Health, this benefit event supports the Cancer Patient Support Program. Enjoy an evening of music, food trucks, a free photo booth, and more. Remaining tickets are $60.

May 10
Tour Pour Du Jour at Graylyn. 4–6 p.m. Enjoy a guided butler tour of Graylyn’s historic Manor House, the former estate of the Bowman Gray family and one of Winston-Salem’s most storied landmarks. Afterward, relax with wine and appetizers in the library. $60 per person.

May 14
NCMA Field Trip: Culture WS. 6 p.m. The NC Museum of Art (SECCA) continues its "Field Trip" series with a visit to Culture WS, a thriving creative hub on the 9th floor of downtown's Liberty Plaza building. This month's trip coincides with its popular Collage Night, allowing guests to explore 30+ artist studios, watch live demos, and participate in a community art-making session. Admission follows NCMA’s “Pay What You Want” model. 

May 15
Lyrics by the Lake (Season Kickoff). 7–10 p.m. This popular spoken word and music series returns for Season 6, moving indoors to the Hanesbrands Theatre while keeping its signature energy and vibe. Hosted by LB the Poet and Mr. P.E.T.T.Y, the evening features poetry, live music, and performances from artists across the region, plus local vendors. Tickets start at $30; season passes are available.

May 15
Art Crush 2026. 7–10 p.m. The Downtown Arts District’s free Friday night block party returns with new experiences, fresh themes, and a refined format. Enjoy street vendors, live entertainment, kids’ activities, extended gallery hours, and handmade art, all centered around Sixth and Trade streets. Each of Art Crush features a different theme; May’s “Color the District” offers a vibrant preview of next month's Pride Festival with hands-on activities, including street painting.

May 15
Outdoor Movie in Bailey Park –Talladega Nights. 7–10 p.m. Downtown’s monthly outdoor movie series continues with this rowdy 2006 comedy starring Will Ferrell and John C. Reilly. Bring a blanket or lawn chair; pets are welcome but must be leashed. Food and drinks (including beer) will be available starting at 7 p.m., with the movie at sunset (around 8:30 p.m.). The screening is part of the “Innovation in Cinema” series by Innovation Quarter and A/perture Cinema.

May 15-17
Winston-Salem Greek Festival. 10 a.m.–10 p.m. Opa! This popular three-day festival returns with authentic Greek cuisine, live entertainment, cultural exhibits, church tours, shopping, and family-friendly fun. Kids can enjoy games and treats, while adults browse vendors. Admission is $5; free for children 12 and under. Held at Annunciation Greek Orthodox Church. 

May 16
Fair Share Farm’s Annual Barn Bash. 10 a.m.–3 p.m. Kick off the growing season at Fair Share Farm in Pfafftown with a family-friendly celebration. Browse a stocked Barnstore with produce and more, and shop from over 20 local food, beverage, bakery, and craft vendors. The day features live music, kids' activities, yard games, farm tours, and door prizes. Admission and parking are free.

May 16
RuralFest 2026. 11 a.m.–9 p.m. Head to Rural Hall's Covington Park for a day of community-oriented fun. The festival features craft vendors and food trucks along with live music kicking off with the Men in Black from 1–4 p.m., followed by the smooth yacht rock sounds of the Camel City Yacht Club from 6–9 p.m. Stick around for the grand finale fireworks show. Admission is free.

May 16
Lewisville: Starlight Movie Night – Jurassic World Rebirth. The Town of Lewisville kicks off its 2026 outdoor movie series with this action-packed 2025 blockbuster starring Scarlett Johansson. Admission is free; bring a lawn chair or blanket. Concessions will be available, and coolers are welcome. No pets or alcohol permitted. Pre-movie activities begin at 6 p.m., with the movie starting at dark.

May 16–17
Carnivorous & Exotic Plant Symposium & Expo. This annual gathering at the Kernersville Recreation & Events Center features over 60 vendor booths filled with rare and unusual species. Attendees can explore special exhibits, join guided tours, and learn cultivation tips from expert speakers. It’s a must-visit for seasoned collectors and curious families alike. General admission is $15.

May 17
MESStival at Kaleideum. 12–5 p.m.  This annual eventlets kids get immersed in gooey, slimy fun at Kaleideum Museum. Activities will be inside and out, from water play and oobleck pools to foam parties and foot painting. The day ends with a Rockstar Bubbles Foam Party. Dress for mess and bring a towel + change of clothes. Included with admission; $10 in advance, $15 at the door. (Free for members)

May 22
Kaleideum After Dark (All-Ages). 5–9:30 p.m. Kaleideum's monthly after-hours party gets a twist this month, blending its typical 21+ vibe with the energy of the Gears & Guitars festival for an all-ages evening. Enjoy live music and the "Streets of Fire" bike races outside the museum before heading in for a K-Pop dance party, Guitar Hero competitions, and a cash bar. It’s the perfect way to experience the museum attractions with a prime view of the festival action. Admission is $5 (free for members).

May 22–23
Gears & Guitars 2026. Billed as “the biggest party on two wheels,” Gears & Guitars brings pro bike racing, community rides, and live music to downtown each Memorial Day Weekend. Friday night kicks off with the "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 free music in Bailey Park.

In addition to the cycling events, admission to all live music at Gears & Guitars is free. Here's the band line up for the 2026 festival: 

• May 22: Friday concerts will be at Merschel Park, just in front of Kaleideum, and headlined by alt-country rising star  Ruston Kelly
  • Noon –  Ears to the Ground
  • 2 p.m. – High School Reunion
  • 5 p.m. –  Ruston Kelly (headliner
• May 23: Saturday concerts take place in downtown’s Bailey Park, featuring a lineup of regional favorites along with leading indie-pop band Saint Motel
  • Noon –  Ears to the Ground
  • 2 p.m. – High School Reunion
  • 5 p.m. – Gods of Grunge
  • 9 p.m. – Saint Motel (Headliner)

May 22-24, 29-31
Theatre Alliance: Everybody’s Talking About Jamie. 7:30 p.m.; Sunday matinees at 2:30 p.m. This feel-good, coming-of-age musical follows a 16-year-old who dreams of becoming a drag queen, navigating school, family, and self-doubt along the way. Inspired by a true story, it’s an uplifting celebration of identity, acceptance, and the courage to be yourself. Performances are at Theatre Alliance (650 W. Sixth St.). Tickets are $23–$25.

May 23
Tonight's Special Comedy Special. 8 p.m. Head to the Milton Rhodes Center for a high-energy comedy variety show featuring a mix of improv, music, and stand-up. Each monthly performance is entirely new, offering a unique "grab bag" of humor that’s never the same twice. It’s a perfect Saturday night out for those looking for fresh local laughs. Tickets start at $15; suitable for ages 18+.

May 24
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.  Happening simultaneously is the free MIXXER Maker Market. Shop for hand-made goods, watch local artist demos, and enjoy and free tours. MIXXER is also where you'll find the Food Truck Festival picnic area.

May 26
Salem Band Concert w/ Paperhand Puppet Intervention.  Salem Band’s free summer concert series opens with a crowd favorite: Paperhand Puppet Intervention, known for their whimsical, larger-than-life creations paired with music from Encanto, Fiddler on the Roof, 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., with the concert at 7:30 p.m. 

May 30
Green Home Tour 2026. 11 a.m.–2 p.m. Get inspired by local sustainability at Piedmont Environmental Alliance.  Explore Winston-Salem houses and gardens featuring solar energy, rain barrel systems, and Audubon-certified habitats. Ticketholders can connect directly with homeowners to learn the first steps toward making their own green improvements, with refreshments available at most stops. Tickets are $20–$35; location details are provided upon purchase.

May 30-31
WS Symphony finale: Copland's Fanfare. Saturday, 7:30 p.m.; Sunday, 3 p.m. In a stirring season finale, the Winston-Salem Symphony presents Copland’s enormous Symphony No. 3 ("Fanfare for the Common Man"). It will be proceeded by a work from Winston-Salem's own Dan Locklair, featuring the poetry of Maya Angelou, narrated by NC Poet Laurate Jaki Shelton Green. Held at R.J. Reynolds Auditorium. Tickets start at $30.

THROUGHOUT THE MONTH

Reynolda Exhibit – Layered Looking: Making Sense of Art 
This immersive exhibition remains on display throughout the spring in Reynolda’s Babcock Wing while the historic home undergoes renovations. The show invites visitors to engage works from Reynolda’s permanent collection through sound, touch, movement, and hands-on exploration during regular museum hours. Like all major Reynolda exhibitions, it will be accompanied by complementary events. May highlights include:

• May 9, 23 – Open Studio Saturday. 9:30 a.m.–4 p.m. Reynolda hosts family-friendly studio sessions on select Saturdays, allowing guests to create a take-home art project. Included with admission ($14 adults; $5 kids; free for dual/family members).
• May 16 – Layered Looking Curator Talk. 2–3 p.m. Layered Looking curator Julia Tanner shares insights into the ideas and creative process behind the exhibit in the Reynolda Auditorium. $25; $20 for members.

May Concerts at The Ramkat. 
Downtown’s premier music venue hosts a strong lineup of regional and national acts this month, including Laura Jane Grace (May 2), featuring Black Guy Fawkes; Let’s Sing Taylor: A Live Band Tribute to Taylor Swift (May 8); Nashville Nights: Ultimate ’90s Country Experience (May 9); contemporary swing favorites Big Bad Voodoo Daddy (May 14); and Grateful Dead tribute Cosmic Charlie (May 16). Additional performances will take place in both the main hall and the more intimate Gas Hill Drinking Room. For tickets and more details, visit The Ramkat’s website.

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 classes are held at the Sawtooth School (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.

Winston-Salem Dash Baseball 
May 1-3, May 12-18, May 26-31
Catch the hometown Dash at award-winning Truist Stadium during three home stands in May. Weekday promotions in May include post-game fireworks every Friday and Saturday (May 1, 2, 15, 16, 29, 30) and Pups in the Park/Thirsty Thursdays (May 14, 28). Tickets start at $10-$14. Don’t miss special theme games such Star Wars Night (May 3), Shag Night (May 15) and Dinos at the Dash (May 31). For more details on weekly promos and standout theme games, check out our Dash 2026 Gameday Guide.

Bowman Gray Racing. (Saturdays) The 77th season of racing at NASCAR’s legendary “Madhouse” rolls on each Saturday night in May, with five race nights featuring multi-divisional races: street stock, stadium stock, sportsman, and modified. Admission: $12 adults, $2 children (6–11), free for kids 5 and under. Gates open at 6 p.m., and races begin at 8 p.m. May highlights include:

• May 02 - Kevin Powell Motorsports 100-lap Modified Race
• May 09 - Twin 25-lap Modified races; 50-lap Street Stock logo
• May 16 - Crash Fest - Skid Race, Demolition Derby & More 
• May 23 - Stadium 100 (100-lap Sportsman Race) 
• May 30 - 100-lap Modified Race

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