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Making weekend plans? Check out these 31+ events in Winston-Salem this weekend (September 25-28), including the Bookmarks Festival, Fall Plant Sale, and Winston-Salem Fashion Week!
Don’t forget to look at our live music guide—it’s updated weekly!
Thursday, September 25
- Paint & Sip – Paint a portrait of your pet while sipping on Cordial Cowboy’s NA drinks at DOSE. A portion of sales benefits Forsyth Humane Society. 6 PM
- Poker Night – It’s time to go all in. Play poker at The Ramkat to support Cancer Services. 5:30 PM
- Gospel Choir – The internationally acclaimed Soweto Gospel Choir performs at Wait Chapel! 7:30 PM
- Collage Night – Let your creativity flow and make new connections at Culture WS! Supplies provided. 6-10 PM
- Mom & Baby Yoga – Take a yoga class with your little one at Kaleideum! 10:30 AM
- Author Talk – The annual Bookmarks Festival kicks off with an opening keynote talk from New York Times bestselling author Hoda Kotb at Reynolds Auditorium! 7:30 PM
- Wine Tasting – Girls’ night out! Unwind with a selection of fall wines at Little Pep. 6 PM
- Vinyl Lounge – Meet fellow music lovers at NCMA Winston-Salem! Bring your records and enjoy listening to analog sound together. 5-10 PM
- Cocktails at Capone’s – Head to Robert Hall’s bar for handcrafted drinks by Thirsty Buffalo! 5-9 PM
- R&B and Poetry – Listen to live R&B and spoken word at Bar Nola! 8-11 PM
- Wine Tasting – Girls’ night out! Unwind with a selection of fall wines at Little Pep. 6 PM
- Author Talk – The annual Bookmarks Festival kicks off with an opening keynote talk from New York Times bestselling author Hoda Kotb at Reynolds Auditorium! 7:30 PM
- Sip For Paws – Support the Forsyth Humane Society by buying drinks at local “sipperies” (think coffee shops and breweries)! Participating businesses will donate 10% of their proceeds to Forsyth Humane Society. All day.
Friday, September 26
- House Hangs – It’s the final House Hang of 2025! Head to NCMA Winston-Salem for a live DJ, dinner from Native Root, sweets by Nougat Desserts, and NA beverages by Cordial Cowboy. 5-8 PM
- Soccer Game – Cheer on the Demon Deacons as they take on Clemson at Spry Soccer Stadium! 7 PM
- Book Launch – Join Louie & Honey’s Kitchen to celebrate the release of co-owner Naomi’s new cookbook, “Amish Baking at Home”! Expect book signings, complimentary treats, raffles, and live music. 3-6 PM
- Decades Party – Jam out to your favorite songs from the ‘70s, ‘80s, ‘90s, and ‘00s with Souljam at Wise Man Brewing—come dressed as your favorite decade! 8-11 PM
- Latin Dance – Join SonCaribe Latin Dance at the Coal Pit for a salsa and bachata dance class, followed by a night of social dancing! 7-11 PM
- Runway Shows – It’s Winston-Salem Fashion Week! Watch models strut unique styles at various venues around Winston-Salem. Shows continue through Sunday.
Saturday, September 27
- St. Baldrick’s Day – Support the St. Baldrick’s Foundation’s fight against childhood cancer at downtown Incendiary Brewing—expect head-shaving, a dunk tank, and raffles! 1 PM
- Bookmarks Festival – Head to downtown Winston-Salem for 50+ authors signing books and participating in panels, a kids’ zone with books and activities, and a food truck court! 9:30 AM – 5 PM
- Apple Festival – Celebrate the autumn season at Bethabara Park with 18th-century craftsmen demonstrations, Colonial games, face painting, and plenty of apples! 10 AM – 4 PM
- Movie Night – Join the Vecino Center for an outdoor screening of “Amélie” and enjoy French pastries on the house! Film in French with English subtitles. 7 PM
- Renaissance Festival – Hear ye, hear ye! Travel to The Brewer’s Kettle in the land of Kernersville for 40+ vendors, medieval combat, raffles, and more. 12 PM – 11 PM
- Silent Disco – Live DJs? Check. Headphones? Check. Looks like it’s time to jam out at The Ramkat! Tickets are BOGO free for all WS/FCS employees. 8 PM
- Fall Plant Sale – Shop for native plants and garden staff favorites at Reynolda Gardens’ plant sale! 8 AM – 2 PM
- Football Game – Cheer on the Demon Deacons as they take on Georgia Tech at Allegacy Stadium! 12 PM
- Bounce House Heaven – Head to Tanglewood Park for the ultimate playground, including a 900-foot blow-up obstacle course and the world’s largest bounce house! Available through Sunday.
- Runway Shows – Fashion Week kicks off at Robert Hall with models strutting unique styles (also featuring looks from local retail boutiques). 1-4 PM
- Kayak the Quarry – Experience The Quarry at Grant Park from the water! Time slots are also available on Sunday. Note: Only tandem kayaks are still available.
- Line Dancing – Join Maggie Shippley at Wise Man Brewing for free beginner lessons! 6 PM
- Swing Dance – Celebrate the 25th anniversary of the Piedmont Swing Dance Society at the Kernersville VFW Post with a free beginner’s lesson and social dancing! 7-11 PM
- Watercolors in the Garden – Capture the beauty of the Single Brother’s Garden with watercolors! 9 AM
- Salem Lake Trail Run – Run a 30K, 7-miler, or 5K at Salem Lake! Proceeds benefit multiple organizations. Races start at 8 AM.
- Singles on Segways – Meet fellow singles while touring Winston-Salem! Starts at Triad ECO Adventures. 9:30 AM
- Fall Festival – Shop unique, handcrafted items at South Fork Community Center! 9 AM -3 PM
Sunday, September 28
- Cocktail Class – Learn how to infuse autumnal flavors into your cocktail creations at easytalk. 4 PM
- Book Swap – Bring a book (or several) to swap with fellow literary lovers at West Bend Bar! 1-5 PM
- Wine Dinner – Enjoy an oyster dinner paired with cider from Cold Hill Farm at Little Pep! 5 PM until sellout.
- Oktoberfest – Grab your lederhosen and head to Brouwerij DuBois for polka dancing, schnitzel & bratwurst, and stein-holding competitions! 12-8 PM
- Closing Keynote – As the final event of the Bookmarks Festival, catch a conversation with New York Times bestselling authors Rick Riordan and Mark Oshiro at R. J. Reynolds Auditorium. 3 PM
- Cake Decorating – Stack, frost, and decorate a three-layer cake at The Canvas Cake Studio! 1 PM
- Vendor Market – Browse handmade items from local makers and artists at Robinhood Plaza. Don’t forget to grab a sweet sip at The Struggle Bus while you shop! 12-5 PM
- Yoga at the Winery – Unwind with a yoga class at Medaloni Cellars! 11 AM
