With so many fun events happening this October, we couldn’t pick just a few. There’s something for everyone on this list – get in the Halloween spirit with these fun, fall happenings!
Oct. 3-31: Kids can select their ideal pumpkin and snap great photos after a Scenic Hayride through Tanglewood Park on a fun, tractor-drawn journey to the patch.
Oct. 3-25: Now celebrating its 13th year, Wicked Whimsies, a fairy-tale–themed spook trail in nearby Pfafftown takes beloved childhood stories and twists them into something far darker on Fridays and Saturdays from 7:30-10:30 pm. Prepare to encounter more than a dozen scary scenes and over 70 live actors as you brave the spooky forest.
October 19: Gather your costumed kids—from monsters to princesses—for the annual Monster Dash and Goblin Hop from 2:00-4:00 pm on the Village Point Greenway in Clemmons, where local businesses offer spooktacular tables and kid-friendly activities to fill their goodie bags.
October 19: Wear your costume and enjoy a friendly-spooky afternoon at Winston-Salem Symphony’s Halloween Spooktacular at Brendle Recital Hall. Enjoy music from Harry Potter, Star Wars, Wicked, and more, plus preconcert fun at 2:00 pm featuring storytelling, crafts, and an instrument petting zoo before the 3:00 pm performance.
October 23-November 2: Don’t miss Evil Dead: The Musical at Camel City Playhouse—a hilariously gory, over-the-top cult classic brought to life.
October 24-November 1: Theatre Alliance presents its 9th Annual Production of The Rocky Horror Show—a wild, interactive, and delightfully risqué Halloween tradition filled with music, madness, and audience participation!
October 25: Meet and greet your favorite superheroes, princesses, and storybook characters at the Character Breakfast, a fundraiser for the Ronald McDonald House; seating is available at 9:30 am at Forsyth Country Club.
October 25: Get ready for Halloween crafts, face painting, haunted hallways, an obstacle course and more at Trick or Treat: Ghoul Times! at Kaleideum from 12:00-5:00 pm.
October 25: Ghost walks + spooky stories will take place at Boo! at Bethabara Park for FREE from 1:30-4:30 pm.
October 25: Celebrate the Ghoul Moon Festival at the West Salem Art Hotel from 4:00–10:00 pm with art and vintage vendors, live music, performances, food trucks, drinks, and spooky contests with big prizes!
October 25: Check out Winston’s best bars at the 2025 Winston-Salem Bar Crawl with check in at Wise Man Brewing between 4:00-8:00 pm.
October 25: Join the Winston Salem Social Halloween Bash at easytalk from 8:00 pm–12:00 am for a spooky night of dancing, complimentary treats, a costume contest with cash prizes, and professional photos to capture all the fun!
October 26: Enjoy a haunting Halloween Organ Spooktacular at Reynolda from 2:00–4:00 pm, featuring spooky tunes on the 1917 Aeolian organ in the grand Reception Hall—perhaps even with a ghostly nod from Halloween-lover Katharine Reynolds herself.
October 26: Bring your costumed pups and enjoy cold drinks with the Knock Out BBQ food truck and Salty Paws Doggie Ice Cream at Tucker’s Tap Yard’s annual Barks, Booze & Boos Halloween Bash from 3:00–6:30 pm, featuring a dog costume contest with entry by donation to Unchain Winston!
October 28: Show off your costume and enjoy an afternoon of fun at Project Pumpkin, the largest student-led community building event at WFU, on Hearn Plaza from 3:00-6:00 pm.
October 30: Witness the magic of this season with Candlelight Concert: A Haunted Evening of Halloween Classics at Millennium Event Center at 8:45 pm.
October 31 & November 1: Kick off your day at Wise Man Brewery with their Boos, Brews and Booze featuring food trucks, costume contests, face painting, live music & more.
October 31: Gear up for Bar Nola’s Annual Halloween Party from 9:00 pm–2:00 am, featuring DJ A Vegas, an exciting costume contest with a $200 cash prize, and complimentary drinks and free snacks + candy with a $30 entry!
