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
Ardmore Art Walk 2025 | Saturday, Nov. 8 | 11 a.m.-4:30 p.m. | Ardmore Baptist Church | Free | Explore artwork from some of the historic neighborhood’s talented residents on front lawns. You’ll find handmade pottery, jewelry, wooden utensils, clothing, art prints, and more.
Piedmont Craftsmen’s 62nd Craft Fair | Saturday, Nov. 22-Sunday, Nov. 23 | Times vary | Benton Convention Center | $11+ | Meet makers, enjoy live art demonstrations, and shop goods like handmade gifts, wearables, furniture, and functional wares from 100+ artists from across the US.
For the fam
African American Oral History of Winston-Salem | Thursday, Nov. 13 | 5:45-7 p.m. | Malloy/Jordan East Winston Heritage Center | Free | Celebrate East Winston’s rich heritage by hearing captivating stories from elders, activists, and neighbors as they share personal and historical experiences that shaped the community.
HanesBrands Holiday Warehouse Sale | Thursday, Nov. 13-Sunday, Nov. 16 | Times vary | Winston-Salem Fairgrounds & Arena | Free | Stock up on clothing basics, holiday gifts, and home goods at one of the biggest sale events of the year. Proceeds will benefit United Way of Forsyth County.
Blue skies and sunshine are forecasted for Saturday’s event.
Courtesy Ardmore Art Walk
Friendsgiving Friendship Bracelets | Saturday, Nov. 15 | 10 a.m.-12 p.m. | Miller Park Community Center | $5 | Celebrate the season of gratitude by creating something special for a friend or someone you admire.
Art Crush: Holiday Market | Friday, Nov. 21 | 7-10 p.m. | Arts District | Free | Enjoy local art and performances, art-making, exhibits, plus discover local talents and organizations within the community.
Greek Bake Sale | Saturday, Nov. 22 | 8 a.m.-5 p.m. | Annunciation Greek Orthodox Church | Indulge in sweet and savory pastries made by Winston-Salem’s Greek community, from loukoumades to baklava and spanakopita.
Seasonal events
The Gingerbread Craft Fair | Thursday, Nov. 6-Saturday, Nov. 8 | Times vary | Masonic Center of Winston-Salem | Free | Find gifts for your loved ones and shop goods from regional crafters, sample freshly baked sweet treats, and enjoy a handmade meal at The Gingerbread Café.
Reynolda Village Holiday Stroll | Saturday, Nov. 22 | 1-5 p.m. | Reynolda Village | Free | Enjoy the magic of the holidays with carolers in Victorian costumes, carriage rides, and visits with Santa as you stroll through the historic village.
Holiday Market & Christmas Tree Lighting | Saturday, Nov. 22 | 2 p.m. | 500 W. 5th St. Building | Free | Soak in the magic of Christmas with a festive celebration, including live music, kids’ arts & crafts, plus a 3-mile fun run downtown.
Turkey Struk 5K | Thursday, Nov. 27 | 7:30 a.m.-2:30 p.m. | Winston-Salem Fairgrounds | $16+ | Get active before the feast and kick off Thanksgiving holiday, and get ready for a groovy holiday — bring at least three canned food items to donate to the We Care House food bank.
Live music
Nightrain: The Guns N’ Roses Experience | Saturday, Nov. 15 | 8 p.m. | The Ramkat | $23+ | Experience the high-energy ambiance as the band pays tribute to one of the most iconic rock ‘roll energy bands in history.
Ethernaut Live: A Night of Jazz with Winston-Salem’s Finest | Friday, Nov. 21 | 7:30 p.m. | Milton Rhodes Center for the Arts, Reynolds Place Theatre | $20+ | Dive into an intimate concert experience featuring Winston-Salem’s own jazz supergroup as they take center stage with spontaneous grooves, smooth harmonies, and masterful improvisation.
Theater
“Sister Act” | Friday, Nov. 7-Sunday, Nov. 23 | Times vary | HanesBrands Theatre | $17+ | Get inspired by the feel-good musical comedy filled with disco hits, heartwarming sisterhood, and high-stakes adventure.
RiverRun Film Screening: 75th anniversary of “Sunset Boulevard” | Saturday, Nov. 8 | 7:30 p.m. | UNCSA, ACE Main Theatre | Watch the special screening exploring the dark sides of Hollywood, plus stay for a talk with Wake Forest University professor emeritus David M. Lubin about his new book.
Try with friends
Book Launch with Diana Overbey: A Historic Dive into Bethabara Park | 2-4 p.m. | Historic Bethabara Park Visitor Center | Free | Discover archival maps, drawings, portraits, and photographs that tell Bethabara’s story, from 18th century, plus stay for the book signing and refreshments.
Sunday Afternoon at the R.J. Reynolds Building | Sunday, Nov. 16 | 3-5 p.m. | Kimpton Cardinal Hotel | $27 | Learn about the historic building, which is approaching its centennial birthday, take a curated tour of the Art Deco skyscraper’s signature features, and seal the night with drinks and conversations.
Winter Painting Pop-Up | Sunday, Nov. 16 | 2-4 p.m. | The Brewer’s Kettle, Kernersville | $36 | Paint, sip, and create a holiday-themed wooden door hanger as your masterpiece to take home and show off to all your friends and family.
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.