Lucky you. You just found WStoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout Winston-Salem each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Festivals
Carolina Classic Fair 2025 | Saturday, Oct. 3-Sunday, Oct. 12 | Times vary | Winston-Salem Fairgrounds | $0+ | It’s that time of the year again, with carnival rides, concert performances, out-of-the-box food combos, and livestock shows.
Fall Festival | Saturday, Oct. 18 | 10 a.m.-3 p.m. | Koren Farms, Mocksville | Free | Fall in love with pumpkins, Alpacas, hayrides, food trucks and crafts by local vendors. Don’t forget to browse from a selection of craft beer and ciders, apple cider slushies, and s’mores.
Shalloween Festival 2025 | Saturday, Oct. 25 | 1-2:30 p.m. | Shallowford Square | Free | Parents, bring your kiddos up to 12 years old for a bewitching array of activities + participate in a costume contest, stay for haunted fun like arts and crafts activities.
Active
Brunch ‘N Burn | Sunday, Oct. 5 | 1-2 p.m. | Footnote Coffee & Cocktails | Free | Workout + brunch? Yes, please. Enjoy a free 1-hour HIIT workout from D1 Fitness + and head over to Footnote to receive 20% off your brunch.
Ardmore Run Against Hunger | Saturday, Oct. 18 |8 a.m. | Redeemer Presbyterian Church | $22+ | Run for a cause and support food-insecure and at-risk families get access to meals and resources. Gather a group or run solo.
More than 900 runners participated in 2022.
Photo by Amber Renea Photography via Ardmore RAH!
Down Dogs & Dogs Yoga | Saturday, October 18 | 3-4 p.m. | Forsyth Humane Society | $25+ | Stretch, strengthen, and snuggle with adoptable dogs (and puppies if available) — bring your yoga mat.
For the fam
Food Truck Fridays in Bermuda Run | Friday, Oct. 10 | 4-9 p.m. | Town of Bermuda Run | Free | Enjoy live music, food trucks, and plenty of kids’ activities in the countryside.
WSSU 2025 Homecoming Week | Sunday, Oct. 12-Saturday, Oct. 18 | Times vary | Winston-Salem State University | Free | The week will start with a lighting show, continue with live performances, a fashion show, a royal coronation ball, and conclude with the homecoming football game of the year.
Visual artists are provided a free table and don’t have to pay a booth fee to participate in ART CRUSH.
Photo by @hiaj via @artsdistrictwsnc
Art Crush: Hispanic Heritage Celebration | Friday, Sept. 19 | 7-10 p.m. | Arts District | Free | Enjoy local art and performances, art-making, exhibits, plus discover local talents and organizations within the community.
Seasonal events
House party: Corporate Takeover 2 | Tuesday, Oct. 7 | 5:01 p.m.-12 a.m. | Fair Witness Fancy Drinks | Free | Bring your business attire and wear your alter ego at this techno and house music event with DJs spinning all night.
Körner’s Folly Oktoberfest | Saturday, Oct. 04 | 1:30 p.m. | Körner’s Folly, Kernersville | $10+ | Celebrate the German heritage tradition with tasting classes, local cuisine, and show off your strength in stein-holding challenges.
2nd Annual Downtown Witches Walk & Winston “the Other” Salem Night Market | Friday, Oct. 24 | 6-10 p.m. | Downtown Winston-Salem | Browse goods from local vendors, enjoy activities like pumpkin carving, trick or treat, music, performances, and more.
Kaleideum’s Ghoul Times 2025 | Saturday, Oct. 25 | 12-5 p.m. | Kaleideum | $7+ | Throw on your favorite costume and trick-or-treat your way through Liberty Plaza and the museum’s exhibits.
4th Annual Halloween Costume Contest | Friday, Oct. 31 | 9 p.m.-2 a.m. | Bar Nola | $30 | Bring your wildest, creepiest, funniest costume for a chance to win a $200 cash prize + enjoy complimentary drinks as you vibe on the deck.
Live music
Evening in the Atrium: de la Fonk | Thursday, Oct. 16 | 5 p.m. | 500 West 5th St. | Get ready for a funky evening under the skyline with a high-energy mix of soul and funk, plus enjoy complimentary bites from The Downtown Grille.
Walk A Mile In My Shoes | Camel City | Saturday, Oct. 18, Tuesday, Oct. 21 | Times vary | Reynolda House | $75 | Watch a powerful storytelling performance, showcasing the music that fueled a movement for racial and economic justice during the 1940s tobacco era.
UNCSA Fall Chamber Music Festival | Saturday, Oct. 18, Tuesday, Oct. 21, Saturday, Oct. 25 | 7:30 p.m. | Watson Hall | $25 | Experience the monumental piece highlighted by Sergei Taneyev’s Piano Quintet — rarely performed and vastly challenging to play, joined by students, other faculty and guest artists.
Ben Folds in Concert | Saturday, Oct. 11 | 7:30 p.m. | RJ Reynolds Auditorium | $70+ | The Emmy-nominated singer-songwriter-composer comes home to perform with the Symphony at his high school alma mater for one night only.
Theater
Hocus Pocus 2 (2022): Starlight Movie Night | Friday, Oct. 10 | 7-9 p.m. | Shallowford Square | Free | Bring friends and family for a cinema experience under the stars and watch the story of how the Sanderson Sisters stop the child-hungry witches from wreaking havoc on the world.
“Mordreadi! A Musical Comedy at Sea” | Sunday, Oct. 19 | 2-4 p.m. | Generations Center, Gallery Theater (Room 211) | Free | The staged reading and musical performance Set sail on the good ship in the swinging 1970s, where Mordreadi, a hapless magician, turns a Greek Isles cruise into a riot of mishaps.
Murder on The 518 | Friday, Oct. 24-Sunday, Oct. 26 | Times vary | Mountcastle Forum | $14+ | Red-eye travelers on the westbound 518 are in for a surprise when the first passenger, and then another, mysteriously drop dead right before their eyes.
Try with friends
End of Days Distillery Tasting | Sunday, Oct. 5 | 2 p.m. | The Dutch Light | $27 | The guided tasting experience offers an award-winning range of spirits + canned cocktails perfect for sipping, plus discover your new favorites.
House party: Corporate Takeover 2 | Tuesday, Oct. 7 | 5:01 p.m.-12 a.m. | Fair Witness Fancy Drinks | Free | Bring your business attire and wear your alter ego at this techno and house music event with DJs spinning all night.
Winston Girls Club: Matcha Class | Thursday, Oct. 9 | 6:30-8 p.m. | Chill Nitro | $65 | Text the girl chat. Learn the art of whisking like a pro and create a delicious matcha latte topped with cold foam at this interactive workshop.
Taylor Swift Karaoke Night | Friday, Oct. 24 | 6:30 p.m. | The Paul J. Ciener Botanical Garden, Kernersville | $10 | Grab your friends and slip through the garden gate for an Eras Tour takeover with local food trucks, vendors, and bracelet swaps.
Workshop: Chinese Calligraphy | Saturday, Oct. 25 | 11 a.m.-2 p.m. | NCMA Winston-Salem (Overlook Gallery) | $19 | Create your own scroll, combining mark-making and visual symbols in a personal, meditative artwork as you learn the history and philosophy behind Chinese characters.
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.