Events

Weekender: 37+ Events in Winston-Salem this Weekend, including Dirty Dozen 5K, Food Hall Invasion, and Fall Vintage Market

Jacob Gauthier

September 10, 2025

Making weekend plans? Check out these 37+ events in Winston-Salem this weekend (September 11-14), including the Dirty Dozen 5K, Food Hall Invasion, and Fall Vintage Market!

Don’t forget to look at our live music guide—it’s updated weekly!

Photo courtesy of YMCA

Thursday, September 11

Climb to Remember – Honor those who lost their lives in the September 11, 2001 terrorist attacks by climbing 2,977 steps at Allegacy Stadium. Free to attend, registration required. 6 AM
Open Mic Night – Join Winston-Salem Writers at The Bookhouse to share your original work! 7 PM
Steak Frites Dinner – Enjoy a three-course meal prepared by Bobby Boy Bakeshop at The Caviste. Seatings from 6-7 PM.
Birthday Bash – Born in September? Celebrate your birthday with a free bubbly drink and cupcakes at Brouwerij DuBois! 6-8 PM

Friday, September 12

Artistic Elements Showcase – Experience a night of creativity at NCMA Winston-Salem as seven local artists share their work—featuring visual art, live music, dance, delicious food, and more! 6-8 PM
Fitness Friday – Join F45 Training in the Coal Pit for a free 30-minute workout and stay afterward to socialize at Cugino Forno! Registration required. 5:30 PM
Movie Night – Watch Disney/Pixar’s “Inside Out 2” at Shallowford Square! Movie starts at dark. Come early to play prize bingo.
Dueling Pianos – This isn’t your average piano concert. Uptown Dueling Pianos performs an all-request, sing-along show at West Bend Bar! 7 PM
Pours & Pilates – Head to Winston-Salem Wellness Collective for a Pilates class and NA drinks from Cordial Cowboy. 6 PM
Hairspray – Good morning Baltimore! Watch Theatre Alliance’s production of “Hairspray,” an award-winning musical set in 1960s Baltimore. Runs through September 21.
Night Market – It’s Wise Man Brewing’s last Night Market of the season! Shop from local vendors, grab a drink, and enjoy live music from Celtic band Banna. 5-9 PM
NC Comedy Fest – Unwind from the week with a comedy show at Marketplace Cinemas, featuring 15 comedians! 8 PM
Ace ‘n Ale – Grab your racquet and head to Hanes Park for Winston-Salem Tennis’ young adult social league! 6 PM
Outdoor Movie – Watch “La Bamba” at Bailey Park! SonCaribe Latin Dance will offer a short dance lesson before the movie starts at dusk.
Author Talk – Join Katherine Scott Crawford as she discusses her new book, “The Miniaturist’s Assistant,” at Brydhouse Books. 6 PM

Saturday, September 13

Dirty Dozen 5K – Race in an obstacle course mud run at the Jerry Long Family YMCA, then join in the Oktoberfest celebration afterward! Races start at 7:30 AM; Oktoberfest starts at 8:30 AM.
Kaleideum After Dark – Test your knowledge with book trivia, sip on the “Tequila Mockingbird,” and explore pop-up book sales set up around Kaleideum! 21+ only. 6:30-9:30 PM
Walk & Roll Fest – Head to Truist Stadium for raffles, food trucks, vendors, and the chance to explore the NEW Twin City Trail with a 5K, bike ride, and kids run! Free to attend. 8:30 AM – 1 PM
Fall Vintage Market – Shop from 45+ local vendors, grab a bite from a food truck, and take a self-guided tour at Körner’s Folly! 9 AM-3 PM
Comedy Show – Get ready for a hilarious night with Bad Momz of Comedy at Reynolds Place Theatre! Show times at 6 and 9 PM.
Children’s Consignment Show – Find fall & winter children’s clothes, toys, books, baby gear, and more at Friedberg Moravian Church. Select items will be half-priced! 9 AM-12 PM
Fashion Exhibition – View “Dandyism, The Rebirth of Refined Style” at the Elberson Fine Arts Center—the reception includes a body painting fashion runway show. 5-8 PM
Plant Sale – Discover native plants, flowering shrubs, trees, and more at N.C. Cooperative Extension, Forsyth County Center. 9 AM-1 PM
Anniversary – Celebrate seven years of Incendiary Brewing’s downtown location with food trucks and a performance by Better Than Ezra at Bailey Park! 6 PM
Walk for Apraxia – Walk at The Quarry at Grant Park to help raise funds for Apraxia Kids’ programs! 10 AM
Singles On Segways – Meet fellow singles while touring Winston-Salem! Starts at Triad ECO Adventures. 9:30 AM
One Act Play Festival – Watch plays written by local playwrights at Camel City Playhouse! Runs through September 21.
Cornhole Tournament – How’s your cornhole game? Test your skills at Bodine’s Bar—amateurs only! 4 PM
Night Market – Shop from 30+ vendors, enjoy live music, and grab a bite from on-site food trucks at Incendiary Brewing in Lewisville. 5-8 PM
Never Walk Alone – Head to Bailey Park for an addiction awareness event, featuring live music, food trucks, interactive activities, and access to recovery resources. 12-3 PM
Painting DIY – Learn how to use the acrylic pour method to create a unique painting at Wine & Design! 7 PM
Classic Car Cruise In – Admire classic cars and connect with fellow enthusiasts at 101 S Main Street in Kernersville! 4-7 PM
Bloom & Reflect – Take it slow at Lizzie’s All Natural Products with a guided journaling session and floral bouquet workshop. 3 PM
Rollin For Rescues – Support Forsyth Humane Society at this Jeep show at North Point Chrysler Dodge Jeep Ram Fiat! 11 AM-4 PM
Latin Dance – Join SonCaribe Latin Dance at AFAS for a salsa dance class, followed by a night of social dancing! 7-11 PM
Family Art Day – Take your kids to NCMA Winston-Salem and create multi-media mythical creatures together! Free to attend. 11 AM-2 PM
Movie Night – Watch the original Aladdin at Main Street Park in Mocksville! Movie starts at dark.

Sunday, September 14

Winston-Salem Food Truck Festival – Grab a tasty meal or dessert from 24+ food trucks lined up on 9th Street! 1-7 PM
Arts on Fire – Watch iron pours and live art demonstrations at Mixxer—you can even become part of the action with hands-on classes! Free to attend. 1-7 PM
Yoga at the Winery – Unwind with a yoga class at Medaloni Cellars! 11 AM
Vendor Market – Shop from 40+ local artisans and specialty vendors, listen to Dustin York perform, and visit a food truck at Foothills Tasting Room! 1-6 PM
Food Hall Invasion – Top-rated chefs serve up delectable meals at Second Harvest Food Bank. The mission? Helping our hungry neighbors eat. 5-7:30 PM
Pickleball Play – Join Average Joe Pickleball for low-key, co-ed matches at Oak Summit Park, followed by brunch at East of Texas! 10 AM
Baking Class – Learn to make classic French desserts like chocolate eclairs from Chef Nguyet Nguyen at Southern Home & Kitchen. 1 PM
Barktember Festival – Celebrate autumn at Tucker’s Tap Yard with a vendor market, specialty drinks, live music, and food trucks! 1-5 PM
Fall Painting – Create a fall-themed wooden door hanger with JK Woodworked Creations at Fiddlin’ Fish! 2 PM