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Making weekend plans? Check out these 33+ events in Winston-Salem this weekend (October 2-5), including the Carolina Classic Fair, Latin Fest, and Camel City Supper Club!
Don’t forget to look at our live music guide—it’s updated weekly!
Thursday, October 2
- Anniversary Gala – Habitat for Humanity of Forsyth County celebrates its 40th anniversary at The Millennium Center, featuring raffles, auctions, and the party band Envision! 5 PM
- Free Yoga – Take a deep breath. Join Lotus Yoga for this year’s final outdoor yoga session at Bailey Park. 6 PM
- Italian Dinner – Enjoy a three-course Italian meal at The Caviste, featuring mushroom arancini and braised short ribs. RSVP required. Seatings from 6 to 7 PM.
Friday, October 3
- Carolina Classic Fair – It’s opening day! Rides, contests, shows, and delicious treats—experience all the fun of the fair at the Winston-Salem Fairgrounds! Available through October 12.
- Listening Party – Enter a new era with “The Life of a Showgirl” at Okay Coffee, paired with treats by The Humble Bee Shoppe and mocktails by Cordial Cowboy. 6 PM
- Sailing for Support – Join Old Nick’s Pub to raise money for the Pretty in Pink Foundation, featuring a ping pong tournament, a cruise giveaway, and karaoke! 7:30 PM
- Happy Birthday – The Little Theatre of Winston-Salem turns 90! Celebrate at The Nash with live entertainment and archival items from their storied past. 7 PM
- Kaleidoscope Ball – Step right up to this circus-themed ball at Kaleideum, featuring games, auctions, and a showstopping performance by High School Reunion! 6:30 PM
- Night Moods – Get ready for the latest installment of NCMA Winston-Salem’s electronic concert series. 7 PM
- Paint & Sip – Paint a ceramic, book-shaped planter at The Bookhouse! 7 PM
- Improv Show – Watch Foolish Mortals, Winston-Salem’s local improv troupe, perform at Camel City Playhouse. 7:30 PM
- Dinner and a/movie – Enjoy dinner at Butcher & Bull followed by a screening of “Julie & Julia” at a/perture! 6:30 PM
- Theatre Show – Head to Hanesbrands Theatre for NC Black Rep’s production of “Purlie Victorious,” a comedy about a Black preacher in the Old South. Show runs through October 19.
- Paint & Trivia – Celebrate the release of “The Life of a Showgirl” with a Taylor Swift-themed painting & trivia night at Wine Design! 7 PM
- The givingRooms – Vote for your favorite interior design vignettes at greeNest—the furnishings and decor items will be available for purchase! Available through Saturday.
Saturday, October 4
- Fall Tent Sale – Save up to 60% off a wide selection of beers and wines at City Beverage and enjoy complimentary brats hot off the grill! 9 AM – 6 PM
- Triad Heart Walk – Join fellow walkers at Triad Park to support the American Heart Association’s research and increase CPR training accessibility. 11 AM
- Kernersville Oktoberfest – Celebrate Oktoberfest at Körner’s Folly with stein-holding & speed pretzel-eating contests, a German spelling bee, and polka music! 3-6 PM
- Moonlight Paddle – Enjoy an evening on the river at Easy Bend Farms. Boats are available to rent. 5-9 PM
- Pink Ribbon Talks – Cancer Services hosts its annual breast cancer conference at the Generations Center, featuring medical and survivor panels. 10 AM – 2 PM
- Uptown Dueling Pianos – Get ready for an all-request, sing-along show at Gypsy Road Brewing! 7 PM
- Candle Workshop – Make a fall-themed candle with Hand the Light at Wise Man Brewing. 11 AM
- Latin Fest – Experience a taste of Latin culture at Bailey Park with music and dancing, lessons, and cultural food trucks! 5-10 PM
- Moon View – Look at the moon through a powerful telescope at Winston-Salem State University’s Fountain Observatory! Free to attend. 7-9:30 PM
- Foothills Oktoberfest – Compete for the best lederhosen, shop from local vendors, and enter a raffle at Foothills Tasting Room! 12-6 PM
- Vintage Market – Shop for your new fall look from 20+ vintage clothing vendors at 675 W 5th Street. 11 AM – 5 PM
- Kids in the Kitchen – Kids will learn how to make hearty eats like beefaroni and Nutella rolls at Southern Home & Kitchen! 10 AM
- Wreath Class – Make a fall-inspired dry floral wreath arrangement at the Kernersville Recreation and Event Center! 10 AM
- Line Dancing – Learn new line dances at Simon’s Community Garden! 10 AM
- Maddie’s Miles – Run in a 5K at Jamison Park to support Phoenix Rising of Winston Salem, Inc., a non-profit that combats addiction through local drug court support. 9 AM
- Mission 5K – Run on a flat course starting at Fleet Feet Clemmons! A portion of proceeds benefits Good Works Engine, a nonprofit helping those in need.
Sunday, October 5
- Space Concert – Salem Band performs music from Star Wars, Dr. Who, and Guardians of the Galaxy at the Elberson Fine Arts Center! Free to attend. 3 PM
- Brunch ‘n Burn – Enjoy a free HIIT workout from D1 Fitness and 20% off brunch at Footnote Coffee. 1 PM
- Decor DIY – Paint the Winston-Salem skyline in a workshop guided by JK Woodworked Creations at Brouwerij DuBois! 2 PM
- Pickleball League – Hit the courts with the Average Joe Pickleball League at Oak Summit Park, then head to East of Texas to keep hanging out. 11 AM
- Supper Club – Join Camel City Supper Club at Fiddlin’ Fish to share a meal with new friends. Don’t forget to bring a dish—this month’s theme is soups and toppings! 5 PM
- Mahjong Class – Learn to play Mahjong with Camel City Mahjong at The Dogwood Boutique! All ages welcome. 2 PM
- New Farmers Market – Head downtown for the first Trade Street Farmers Market, featuring 15+ local vendors! 10 AM – 2 PM
- Family Workshop – Use cardboard and stamps to design a building or city scene at Reynolda House Museum! Intended for children grades 1-6. 2 PM
- Halloween DIY – Paint a picture inspired by Pennywise from Stephen King’s “It” at Radar Brewing! 2 PM
- All Mounds Matter 5K – Run in a 5K or 1 Mile Fun Run at Savage Roasters Coffee to support Cancer Services! Races start at 9 AM.
- Incendiary Oktoberfest – Enjoy German music, free bratwurst, and fall beer releases at Incendiary Brewing in Lewisville. All day.
