11 Signature Fall Events Not to Miss in Winston-Salem

As the temperatures drop and the leaves begin to change, Winston-Salem celebrates the season with many fall festivals and events. From fairgrounds to beer gardens to book readings, the calendar is packed with fresh ways to celebrate each month. Fall is also a beautiful time to visit for scenic drives to beautiful state parks and crisp afternoons on winery patios. Mark your calendar for one (or more) of these fun events. 

Winston-Salem Food Truck Festival 
September 14 — 1 to 7 p.m.
Food trucks from across the state will line East 9th Street, serving up everything from Colombian and Japanese to Thai cuisine and more. There will also be live entertainment, plus beer and wine vendors. If you have a sweet tooth, they’ll have food trucks to satisfy that craving, too. 

• Good to Know:  On the same day, you can check out Arts on Fire held from 10 a.m. to 10 p.m. in the Mixxer Community Makerspace just steps from the Food Truck Festival. One of the main highlights is the Iron Pour, where artists melt down scrap metal and transform it into new works of art. Over 20 craftspeople take over “Artisan Alley,” so you can grab a bite from the food trucks, then browse hand crafted goods and support local artists.

Hispanic League Annual FIESTA! 
September 20 — 11 a.m. to 7 p.m.
Each year, over 20,000 people come together to kick off Hispanic Heritage Month in downtown Winston-Salem. Just outside the Milton Rhodes Center for the Arts, you’ll find food vendors serving a wide variety of Latin American cuisine, along with live music, entertainment, and community resources. Now in its 33rd year, this free event has become a popular celebration of culture, diversity, and family-friendly fun.

Apple Fest at Historic Bethabara Park 
September 27 — 10 a.m. to 4 p.m.
Celebrate the first Saturday of fall with a day full of crafts, Colonial games, face painting, and plenty of apples! Regional musicians will provide live entertainment, including Ken Bloom, who will play the bowed dulcimer. You can explore 18th-century history through demonstrations by traditional craftsmen, browse local artisan booths, and grab a bite from your favorite food vendors.

20th Annual Bookmarks Festival
September 25-28 — times and venues vary
As the largest annual book festival in the Carolinas, this four-day event is a must for any book lover. The festivities begin on Thursday with an opening keynote by Hoda Kotb, the award winning former co-anchor of NBC News’ Today and co-host of Today with Hoda & Jenna. On Friday evening, the popular Books & Bites event will be held at The Benton where you can mingle with the authors, have books signed, and munch on small bites. The main event takes place on Saturday with authors, vendors, food trucks, and more set up around Bookmarks Bookstore. This part of the festival is free and you can attend various panels throughout the day. Sunday there will be a closing keynote featuring Rick Riordan and Mark Oshiro. Some events are ticketed and take place at venues throughout the city.

Carolina Classic Fair
October 3-12 — times vary by day
The Carolina Classic Fair has been a Triad tradition for going on 143 years. At the fairgrounds, you’ll find classic rides, fair food, and nonstop entertainment from glassblowing and loom weaving to magicians and live music. Don’t miss the butter sculpture or the chainsaw carving demos, and be sure to wander through the Education Building to check out the competitive exhibits, with  entries from people all over NC in categories ranging from fine arts and crafts to agricultural items and food preservation. Kids will love the petting zoo and livestock events, especially the racing pigs. 

Out at the Movies International Film Fest
October 2-5 — times and venues vary
Now in its 12th year, the Out at the Movies International Film Festival showcases around 40 LGBTQ+ films, hosts 8–10 talkbacks, and throws nightly parties over the course of four days. Its mission is to celebrate the best LGBTQ+ films from around the world while encouraging a stronger sense of community. Since it began in 2013, it has grown into the second-largest LGBTQ+ film festival in the Carolinas. Visit their website to stay updated on venue and ticket details.

Kernersville Oktoberfest
October 4 — 3 to 6 p.m.
This beer and food festival takes place on the first Saturday in October at Kernersville’s most unique attraction, Körner’s Folly home. Sample craft brews from local breweries and enjoy bite-sized pairings from area restaurants. Participate in quirky contests like stein-holding challenges, speed pretzel-eating, and even a German spelling bee. Your ticket also includes a self-guided tour of Körner’s Folly, which was built in 1880 by interior and furniture designer Jules Körner. 

Yadkin Valley Grape Festival
October 18 — 11 a.m. to 5 p.m.
Just 25 minutes from downtown Winston-Salem, Yadkinville hosts an annual festival featuring Yadkin Valley wineries, food trucks, and local craft vendors. Wine tasting tickets include a souvenir glass and samples from each winery tent. As the gateway to the Yadkin Valley, Winston-Salem makes the perfect home base for a weekend of wine tasting and festival fun!

Ardmore Art Walk
November 8 — 11 a.m. to 4:30 p.m.
Wander through one of Winston-Salem’s most charming neighborhoods during the Ardmore Art Walk, a juried event that features local artists, live music, and food trucks. All participating artists have a personal connection to Ardmore, and their work must be handmade and sold in person. Spend the day enjoying performances from local musicians and browsing a wide variety of art across different mediums and experience levels.

Piedmont Craftsmen Fair 
November 22-23 — times vary by day
The Piedmont Craftsmen Fair brings over 100 fine artisans from across the country to the Benton Convention Center the weekend before Thanksgiving. You can find a wide range of items like handmade works in clay, wood, glass, fiber, metal, leather, photography, and more. Celebrating 62 years this year, it’s the perfect place to find gifts for the holidays or pick up something special for your home. Tickets are required for admission.

Turkey Strut 5k 
November 27  (Thanksgiving) — 9 a.m.
Kick off Thanksgiving with a 5K that gives back. Proceeds from the race support the We Care House, an outreach program of St. Peter's World Outreach Center that provides food and clothing to families in need throughout Winston-Salem and the surrounding area. The race takes place at the Winston-Salem Fairgrounds and offers both a 5K and 1-mile option.

Check out our online Events Calendar for a full list of the events happening this fall. Start planning your visit by requesting a free Visitor Guide or signing up for our email newsletter.