Oct. 1, 15 
Manolo Boutique Wine Tasting. Join us every 1st and 3rd Wednesday for an evening of exquisite wine tasting at Manolo's Boutique Wines & Bistro. Sip and savor a selection of premium wines from Italy’s most iconic regions. Whether you're a wine enthusiast or just love a good glass, this is the perfect way to explore new flavors and enjoy a charming night out. See you there! 

Oct. 1-31 
Mystery & Mayhem SEGWAY Tour. Experience the Mysteries of Winston-Salem by a Segway Tour! This SEGWAY tour takes you through a winding tale of suspicious stories, mysterious mayhem, and local chaos as we glide through the streets of Winston-Salem. Take a tour of the town while your guide weaves tales of murder, suspicion and quirky circumstances. From spooks to specters, to ne’er-do-wells, this segway tour has it all. 

Oct. 1-31 
Reynolda Exhibit: Camel City: Tobacco & Transformation, 1875–1964. On display this fall at Reynolda House Museum of American Art, this striking exhibit traces the rise and legacy of R.J Reynolds Tobacco amid the company's 150th anniversary. The story is brought to life through rare artifacts, historic images, bold advertising, and several fine art commissions, showing how the Reynolds Tobacco empire shaped Winston-Salem and impacted consumer culture worldwide. It will be complemented by a number of programs and special events throughout the fall, from curator talks to cocktail evenings.

Oct. 2 
Camel City Blues. Winston-Salem based Camel City Blues will perform at Incendiary Brewing Company. A duo/trio/quartet that combines several genres but are solidly rooted in the Blues.

Oct. 3-31 
Pumpkin Pick Hayrides at Tanglewood. Take a scenic tractor-drawn hayride through Tanglewood Park to a pumpkin patch where kids can choose a pumpkin and snap plenty of photos. Offered all October on pre-scheduled weekend rides. Have a big group? You can book a private hayride for groups of 20–30 riders. Reservations are required. To reserve a spot, call 336-766-9540. The cost is $11 per person for a private ride (available weekends in October only) or $220 for a private ride (available any day in October). Cash or check only!

Oct. 3 
DADA 1st Friday Gallery Hop. Explore various downtown art galleries and get a glimpse of local artists works of arts. At various locations in downtown Winston-Salem. 

Oct. 3-25 
Wicked Whimsies. Now in its 13th year, this fairy-tale–themed spook trail in nearby Pfafftown twists beloved childhood stories into something far darker than the Grimm Brothers imagined. Encounter more than a dozen eerie scenes and 70+ live actors as you wander the haunted forest. Recommended for ages 12 and up; glow sticks are available to signal actors to soften the scares. Tickets start at $15.  Wicked Whimsies runs Fridays and Saturdays from 7:30–10:30 p.m. Get tickets here!

Oct. 3-12 
Carolina Classic Fair 2025. Celebrating 143 years of fun, the 2025 Carolina Classic Fair presents the theme "Barn to Be Wild." This year's theme honors the agricultural heritage while capturing the fair's high-energy spirit. From October 3-12, 2025, fairgoers can expect thrilling rides, wildly delicious food, and unforgettable experiences for the whole family. With something fun for everyone, you won't want to miss this fantastic tradition.

Oct. 4
Kernersville Oktoberfest. 3-6 p.m. Craft beer enthusiasts can look forward to tasting German, Oktoberfest, and Pumpkin brews, as well as other seasonal beverages during the annual Kernersville Oktoberfest at Körner's Folly. Local restaurants donate delicious small bites and local breweries pour tastings of their classic brews, while contributing to a great community cause! Each ticket includes beverage and food tastings, a souvenir tasting glass, and a house tour of historic Körner’s Folly. Tickets begin at $40 (this is a 21+ event).

Oct. 4 
Bailey Park Latin Fest. Join us for a vibrant evening filled with music, dancing, live performances, and a variety of food trucks! Experience the rich culture and flavors of Latin America right in our community. The event is from 5-10 p.m. at Bailey Park. Admission is free. Bring your friends and family for an unforgettable night. Don’t miss out on the fun—join us in celebrating Hispanic Heritage Month! 

Oct. 4
WSSU Rams Football vs. Virginia Union University. Head down to the iconic Bowman Gray Stadium and stomp your feet along with the Red Sea of Sound! Cheer on the WSSU Rams football team at home as they take on the Virginia Union University Panthers.

Oct. 6 
Murder at Raven’s Cove: An Interactive Mystery Experience. Step inside the crumbling Poe Mansion in Wraith’s Cove, where a vanished housekeeper and a shocking murder set the stage for gothic intrigue. Mingle amid ghoulish gossip and light reading (bring glasses!). Costumes welcome, not required. Incendiary Brewing, 7 p.m. Tickets: $35 individual, $55 couple. Advance purchase required. 

Oct. 6, 13, 20, 27 
Twin City Trolley Tour. Spend up to two hours exploring Winston-Salem’s landmarks and history aboard a stylish, air-conditioned trolley with cushioned seats and a lively guide. The route highlights Old Salem, Innovation Quarter, the Arts District, Historic West End, Graylyn Estate, Reynolda Gardens, WFU, plus select local shops. Tickets can be purchased in advance online or call 336-722-7777. 

Oct. 10 
Food Truck Fridays in Bermuda Run. Come out and enjoy a Friday evening full of fun with the family and try various local cuisines of the various food trucks.

Oct. 11 
Cars & Coffee: Porsche at NCMA Winston-Salem. Cars & Coffee is free and open to the public. After perusing the automobiles, be sure to explore the art galleries at NCMA Winston-Salem. Cars & Coffee is a safe and family-friendly celebration of cars and the car community. To ensure all attendees and participants have an enjoyable experience, please follow the rules. Anyone found to be breaking the rules will be suspended from participating in future Cars & Coffee events. 

Oct. 16 
Blinds Boys of Alabama. Six-time GRAMMY® winners and Gospel Music Hall of Famers, the Blind Boys of Alabama have spent 70+ years redefining gospel—collaborating with artists from Eric Clapton and Prince to Bonnie Raitt and Willie Nelson. Doors 7 p.m., show 8 p.m. 

Oct. 17 
Oyster Roast at Shelton Vineyards. Get ready for an unforgettable evening of coastal flavors and vineyard views at a festive Oyster Roast & Low Country Boil in the heart of Yadkin Valley. Your $65 ticket includes a welcome wine cocktail, two glasses of wine, a full coastal dinner with sides, a fresh starter salad, and bite-sized desserts—tax and gratuity included. 

Oct. 17-31 
Old Salem Night Watchmen Tours. Embark on a spine-tingling journey through Old Salem this Halloween with the Night Watchman Tours! Join costumed guides on lantern-lit walks, venturing into the original buildings where chilling tales and mysteries unfolded. This immersive tour is designed for ages 10+ and runs for 60 minutes. Tickets are $50. Tours will be held six nights in October (Oct 17-18, 24-25, 30-31) and are likely to sell out. Tours depart every 15 minutes between 6:30 pm and 7:45 pm on each date. Dress warmly and wear comfortable shoes, as the tour is partially outdoors and explore uneven streets and buildings with stairs. 

Oct. 17 
Art Crush. This event is held on the Third Friday of every month from 7-10 p.m. on Trade Street and 6th Street in the heart of the Arts District of Winston-Salem, NC. Established members of the community curate the visual artists and performers of Winston-Salem to provide you with a night of creative expression, exploration and celebration! This event is free to the public.

Oct. 17, 18, 24
Carolina Thunderbirds Hockey. Catch the action on the ice at the Winston-Salem Fairgrounds Annex as you cheer on the Winston-Salem Thunderbirds! With three home games this month, grab your tickets today!

Oct. 18
Innovation in Cinema Series: "Little Shop of Horrors" This free movie screening in downtown's Bailey Park will feature the cult classic "Little Shop of Horrors," just in time for the Halloween season. Food and beverages will be available for purchase from local food trucks. Pets must be leashed, BYO picnic blankets and lawn chairs. 

Oct. 18 
Garden Sprouts: Pumpkin Patch. Celebrate the season with a festive hayride through Reynolda’s Meadow! Families are invited to explore the outdoor Meadow Classroom through hands-on Pumpkin STEM activities and nature-based play. Children will choose a pumpkin from the field and decorate it using natural materials gathered from the gardens and grounds. This Garden Sprouts program is suggested for children ages 2-10, accompanied by an adult caretaker. Rain date is scheduled for Sunday, October 27. 

Oct. 18 
Joytoberfest at Joymongers. This annual fall celebration at Joymongers Barrel Hall channels a German-style Oktoberfest with steins, music, and plenty of cheer. Local favorite Ears to the Ground provides the soundtrack as guests celebrate all day and dance into the night. Admission is free. 

Oct. 19 
Monster Dash & Goblin Hop. The annual Monster Dash and Goblin Hop invites kids to dress up and “goblin hop” along the Village Point Greenway, where local businesses host games, crafts, and giveaways. Activities include pumpkin golf tee hammering, mummy-apple making, beanbag tosses, spoon races, and dance lessons. Kids collect candy, toys, and fun prizes at every stop. Rain date: October 26. 

Oct. 21 
Drop In for a Spell: Witch Hat Decoration Station. Gather at CasaShanti from 12–5 p.m. for a spellbinding Make and Take Witch Hat Decorating event. Step into an enchanting space where cauldrons bubble with creativity and tables overflow with mystical trimmings—velvet ribbons, shimmering stones, glittering charms, and silken feathers await your magical touch. Whether you’re conjuring a whimsical or daringly dark hat, all materials are provided—just bring your imagination and get ready to brew up something extraordinary before Friday’s Witches Walk! Cost: $13 includes supplies.

Oct. 21 
Jazz: Christian McBride, bass, & Brad Mehldau, piano. Two of the most respected artists in contemporary jazz join forces. Brad Mehldau’s “intimate piano voice” partners with Christian McBrides's “sophistication and swing”. This longtime friendship and musical camaraderie have led to various collaborations through the years including the albums Mood Swing (1994), Round Again (2020), and Long Gone (2023) with Joshua Redman and Brian Blade. Tickets: $10-$25, Free with WFU ID. 

Oct. 24 
Second Annual Downtown Witches Walk. The Second Annual Downtown Witches Walk takes place Friday, October 24, from 6–8 p.m. Participants will gather at CasaShanti before strolling through the Downtown Arts District, visiting shops to collect letters that spell a secret magical word. Return completed cards to CasaShanti for a raffle ticket and the chance to win a prize; purchases at participating shops earn extra raffle tickets, though buying is not required. This free event invites guests to dress in their best witchy attire and enjoy an evening of community spirit and enchantment. Participating locations will be announced soon. 

Oct. 25 
Ghoul Times at Kaleideum. Let the ghoul times roll with a day of costumes, crafts, face painting, and trick-or-treating inside and outside Kaleideum. Families can enjoy wacky science experiments, a haunted hallway and obstacle course, rooftop dance party, and food trucks along 3rd Street. Admission is $7 online or $10 day of; free for children under 1. 

Oct. 25 
Boo! At Bethabara. Enjoy listening to spooky song selections in the 1798 Gemeinhaus; meeting a few “spirits" of Bethabara's past during a walk to God's Acre; gathering under a tent to hear ghost stories by acclaimed storyteller Cynthia Moore Brown; making a corn husk doll; watching Glen Yost's sleight of hand magic show; playing Colonial games; getting your face painted; visiting the Forsyth County Public Library Bookmobile; and more. Admission is free. 

Oct. 25 
Winston-Salem Halloween Bar Crawl. Get ready for a night of haunted fun at the Halloween Bar Crawl. Starting at 4 p.m., you’ll move from one spooky venue to the next, guided by a Halloween-themed Digital Bar Crawl Map that lists every participating bar and its specials. Be sure to check your email for event updates and promotions before you head out. To join the crawl, you must check in on time to receive your wristband; if you arrive late, you may not be able to participate. A friend can pick up your wristband with proof of purchase if you can’t make check-in. Remember, this event is for guests 21 and older, and all bar specials are subject to change at the venues’ discretion. Party responsibly and plan ahead for a safe ride home. All sales are final, with no refunds or exchanges. 

Oct. 25 
Ghoul Moon Festival. The West Salem Art Hotel, in partnership with The Full Moon Crew, hosts a magical community event uniting art, makers, and vintage vendors with live music, visual and performing arts, and hands-on workshops led by local artists and nonprofits. Guests can enjoy spooky contests with big prizes, plus tasty bites from local pop-ups and food trucks, along with plenty of beer and beverages. The event runs from 4–10 p.m. 

Oct. 25 
Hoots Scared Stupid Halloween Bash. Come out and enjoy a Halloween Costume party with live music at Hoots Beer Co. from 7-11:55 p.m.

Oct. 26 
Murder is Forever at Radar Brewing - A Murder Mystery Game. Step into espionage at Murder Is Forever, Mystery Men Productions’ spy-themed mystery at Radar Brewing Company. In Dr. Vanessa Silverthumb’s lavish labs—where the ex-villain claims to be reformed—guests mingle with secretive VIPs, from Kitty A. Plenti and Sebastian Dusk to MI17’s tech wizard Q Veecee and Director “Em” Stump. When disaster strikes, agent Jimmy Dawn leads the race to unmask the killer. Bao Yeah! serves Asian-fusion bites 6–9 p.m. Dress in tuxes, gowns, or spy-chic. Tickets are $30, 21+; food and drinks sold separately. 

Oct. 27 
Barks, Booze & Boos Halloween Bash at Tuckers Tapyard. Pick the perfect costume for your pup and enter them into the contest. Each entry requires a $5 entry fee which will be donated to Unchained Winston. Then take your dressed up pup over to the DesiLu Pup Photo Booth to capture some awesome pictures. My Kitchen will be on-site, and we will be serving up some special spooky cocktails. 

Oct. 30 
Cocktails at Capone’s. Unwind, sip, and savor at Cocktails at Capone’s on the last Thursday of every month for handcrafted drinks by Thirsty Buffalo Beverage Catering, good company, and a laid-back atmosphere. Whether you're catching up with friends or winding down after work, this is the perfect spot to raise a glass. 

Oct. 30 
Candlelight Concert: A Haunted Evening of Halloween Classics. Experience a spine-tingling Candlelight concert inside the historic Millennium Center during this special concert titled "A Haunted Evening of Halloween Classics." During the show, classical musicians with the Listeso String Quartet will perform Halloween-inspired works amid a glowing sea of candles. The hour-long show blends spooky favorites like "Thriller" and "Ghostbusters" along with songs from The Exorcist, Stranger Things, Halloween, Beetlejuice, and more. Doors open at 8 p.m. with music starting around 8:45 p.m. Ages 8 and up are welcome; under 16 must be with an adult. 

Oct. 31 
Downtown Kernersville Trick or Treat. Kernersville’s 30th Annual Downtown Trick or Treat will be from 6-8 p.m. Put on your masks, capes, and robes and grab your buckets and bags as we venture along the sidewalks of Downtown Kernersville in search of yummy treats. Hosted by the Kernersville Chamber of Commerce, TOK-Parks & Recreation, and the Kernersville Police Department. This event provides a safe and fun opportunity for kids to visit Downtown Kernersville and meet business owners while filling up your candy bag! 

Oct. 31 
Spirited Halloween Ball at Körner's Folly. Körner’s Folly in Kernersville hosts the 2025 Spirited Halloween Ball, a Victorian-inspired celebration with snacks, drinks, costumes, and mysterious entertainment. Guests join The Ghost Girls for a guided paranormal investigation of Jule Körner’s 1880 home, spanning three floors and seven levels, with tours beginning on the hour at 7, 8, 9, and 10 p.m., limited to 15 people per group. Before and after their investigation, guests can enjoy seasonal brews, cocktails, and mocktails from Breathe Cocktail Lounge, hors d’oeuvres by The Board Babe, music by DJ Spectral Frequency, and a spooky popup by Badkat Beadworks. Great State Paranormal explores Victorian Spiritualism and the tools of ghost hunting, while The Witching Hour offers included tarot readings and Spirit Quest provides aura photography for an additional fee. Doors open at 6 p.m. 

Oct. 31
Boos, Brews, and Booze Halloween Bash. Wise Man Brewing hosts a two-night Halloween celebration on Friday, October 31, and Saturday, November 1, featuring special beer releases, food trucks, face painting, fire spinning, and free live music. A ticketed voodoo doll–making class will be held Friday at 6 p.m. Guests are encouraged to wear their best costumes for a chance to win prizes in the nightly contests. The event is family-friendly and promises two evenings of hauntingly good fun.