Weekender: 28+ Events in Winston-Salem this Weekend, Including Western NC Benefit Concert, Carolina Classic Fair, and New Bookstore

Making weekend plans? Check out these 28+ events in Winston-Salem this weekend, including a Western NC Benefit Concert, the Carolina Classic Fair, and a new bookstore!

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

Thursday, October 3

• ConvergeSouth 2024 – Attend Flywheel’s large-scale startup expo and digital media + marketing conference at Biotech Place. Runs through Friday.
• Bourbon Series – Sample premium bourbons, whiskeys, and ryes at The Kimpton Cardinal Hotel while exploring the historic building. 6 PM
• Free Yoga – Stretch out with Lotus Yoga at Bailey Park! Remember to bring a mat. 6 PM
• The Pink Couch – Join REACH Women’s Network at Project Space 411 for a conversation between female storytellers and entrepreneurs. 5:30 PM
• Benefit Concert – Ears to the Ground performs at Incendiary Brewing! The concert will raise funds for the American Red Cross and The App State Disaster Relief Fund. You can also bring items to donate. 6 PM
• Nonpartisan Candidates Forum – Candidates from all backgrounds discuss their platforms and answer audience questions at Galiliee Missionary Baptist Church. 6:30-8:30 PM

Friday, October 4

• Carolina Classic Fair – The fair officially opens at the Winston-Salem Fairgrounds! Opening day tickets are only $5. The fair will be in town until October 13.
• Free Line Dancing – Learn how to line dance, then show off your new skills during the open dance at East of Texas. 8-10 PM
• Trunk Show – Artfolios presents “Rooted and Grounded” at The Gallery at Stimmel, featuring the works of two local artists. 6-9 PM
• First Friday – Browse a vendor market, jam out to live music, and explore the works of the featured artist of the month at Wise Man Brewing. 5-8 PM
• Ribbon Cutting – Celebrate the reopening of the Trolley Pub with a ceremony conducted by Mayor Allen Joines, free food, and live music. 12-2 PM
• Kaleidoscope Ball – Join Kaleideum for cocktails, dinner, and dancing at a Willy Wonka-themed ball! This event helps the museum provide access and programs to those who otherwise couldn’t afford it. 6:30-11:30 PM
• Fall Photo Walk – Practice your photography with Sawtooth at the Carolina Classic Fair. All skill levels are welcome. 7:30 PM
• “The Shining” Parody – Watch this musical parody of Stephen King’s masterpiece at Theatre Alliance of Winston-Salem. Runs through Sunday.
• Children’s Consignment Sale – Find fall and winter clothing + Halloween costumes, strollers, and baby items at Messiah Moravian Preschool! Runs through Saturday.

Saturday, October 5

• Forsyth Woman Boutique Crawl – Visit several boutiques in and around Winston-Salem with Forsyth Woman Magazine. Your admission ticket enters you into the grand prize drawing, valued at $1800! 5 PM
• Oktoberfest Carnival – Celebrate Oktoberfest at Foothills Tasting Room with stein-holding & lederhosen competitions, carnival games, and polka music! 12-5 PM
• Shred For A Cause – Support Riverwood Therapeutic Riding Center by shredding your important documents at The Children’s Center. 9 AM – 12 PM
• Grand Opening – Visit Kernersville’s newest bookstore, Byrdhouse Books! 10 AM – 4 PM
• Singles On Segways – Join Triad Eco Adventures on a segway tour and mingle with other singles ages 30-45. 9:30 AM
• Heart Walk – Walk in Triad Park to support the American Heart Association! 11 AM
• Kids Symphony – The Winston-Salem Symphony brings Karen LeFrak’s Sleepover at the Museum to life at Kaleideum at 3 PM! Second performance on Sunday.
• Kernersville Oktoberfest – Ein Prosit! Raise your glass (or stein) at Körner’s Folly and take a tour of the historic home. 3-6 PM
• Outdoor Concert – The Kruger Brothers perform at Shallowford Square! Attendees are invited to bring non-perishable food donations for the Lewisville Community Assistance Program. 4:30 PM
• Collectible Show – Explore a huge selection of sports cards, Pokémon, Funkos, comics, and more at Truist Stadium. 9 AM – 4 PM
• Maddie’s Miles – Run in a 5K at Jamison Park! Proceeds benefit Phoenix Rising of Winston Salem, Inc., a non-profit combating addiction through local drug court support. 9 AM
• Ride For WNC – Ride with CycleBar; all proceeds from this ride will go toward organizations assisting families in Western North Carolina. 12 PM
• Latin Fest – Experience the rich culture and flavors of Latin America at Bailey Park with music, live performances, and dancing! 5-10 PM
• Fundraiser Paint Night – Paint with Wine & Design and help raise money for the NC Disaster Relief Fund. 7 PM

Sunday, October 6

• Incendiary Oktoberfest – Join Incendiary Brewing in Lewisville for stein specials, live music, and free bratwurst while supplies last. All day.
• Fall Vendor Market – Shop from local vendors at Joymongers Barrel Hall! Bonus: The Humble Bee Shoppe will be hosting a cupcake decorating class at this market. 2-5 PM
• Haunted Wine Run 5K – Run through the beautiful scenery of Divine Llama Vineyards in this Halloween-themed race. 12 PM
• Calligraphy Class – Join Sip & Script at Joymongers Barrel Hall to learn the basics of calligraphy and letter a faux pumpkin! Supplies included. 4:30 PM