colorful holiday lights in trees

The Best Annual Winston-Salem Events for Your Calendar

With the holiday season just around the corner, we started thinking about all the great events in Winston-Salem. We’ve put together something for each month, starting with the “most wonderful time of the year.”

Annual Winston-Salem events

Whether it’s holiday cheer, chocolates or fine crafts, Winston-Salem has so much to offer both residents and visitors alike. The diversity of annual celebrations is astounding and covers the arts, fashion, culture, heritage, and of course, food and beverage.  Here’s just a sampling.

December events in Winston-Salem

Take a step back to Christmas Past, rekindle holiday memories with a classic ballet performance, and revel in a festival of lights.

Holidays at Reynolda: Christmas-themed historic house tours, caroling, family-friendly activities and more can be found on the 170 acres that comprise the Reynolda House Museum of American Art, Reynolda Gardens and Reynolda Village.

Holidays at Old Salem: Take a walk back to the 1800’s with a Moravian North Carolina Christmas. Enjoy an abundance of greenery, decorated “pyramid” trees and tasty treats from the popular Winkler Bakery.

The Nutcracker at UNC: The holiday season just doesn’t seem complete without this classic ballet. The ballet features UNCSA students who are dancers, musicians, theater designers, and technicians. And Tchaikovsky’s masterpiece is performed by the UNCSA Symphony Orchestra. A Winston-Salem favorite since 1966.

Festival of Lights at Tanglewood: Let there be lights – and Tanglewood Park has ‘em! Fill up the car and take a tour. And you can start 2024 with a foot race through the lights at midnight New Year’s Eve.

And speaking of New Years Eve …

new years eve dance party 2024 millennium center

Millennium Center’s New Year’s Dance Party: Looking to raise the bar on your New Year’s celebration? Dance into 2024 with Millennium house DJs and 815 Events. Complimentary champagne toast and breakfast. Cash bar. General admission and VIP tables. Get your tickets here.

More top annual events, month by month

While December is full of holiday events in Winston-Salem, there’s something happening every month. Here are a few more annual celebrations and festivals to put on the calendar.

JanuaryCarolina Weddings Show: Held at the Winston-Salem Fairgrounds, this is one of the longest running wedding shows in the region and known for amazing fashion shows. 

FebruaryGreensboro Wine & Chocolate Festival: Just over in nearby Greensboro the Coliseum, you can celebrate great wines and chocolates from North Carolina.

Celebrate Spring in Winston-Salem

Spring kicks off in Winston-Salem with beautiful botanical garden blooms, then takes us to a well-regarded film festival, the largest Earth Day Celebration in NC and wraps it up with the biggest party on two wheels.

beautiful tulips in shades of pinkMarchPaul J Ciener Botanical Garden: Celebrate Spring with the beginning of the blooms. Starting in late March and all through April, witness the Spectacular Tulip Bloom.

AprilRiverRun International Film Festival: This 10-day festival serves as an Oscar-qualifying event for filmmakers. Full length features as well as film shorts are showcased.

Also in April, locals and visitors alike celebrate the Piedmont Earth Day Fair. It the biggest Earth Day celebration in North Carolina.

May Gears and Guitars: Held in Winston-Salem’s Innovation Quarter, this weekend event combines world class cycling and live music. It’s the biggest party on two wheels!

Annual Summer events in Winston-Salem

June and July find locals and visitors celebrating African American culture and international Black performing arts, while the city plays host to world class tennis in August.

JuneJuneteenth Festivals: Enjoy rich African American cultural traditions, Afrocentric fashion and collectibles, and a soulful culinary court. There are also two stages of entertainment, a kid’s area, and special exhibits

JulyInternational Black Theatre Festival: The North Carolina Black Repertory Company takes the stage for six days of performances, poetry, film, and more. 

AugustWinston-Salem Open:  Held at the Wake Forest University Tennis Complex, this annual tennis tournament serves as the final ATP Tour stop before the US Open. See all the greats at this international tennis event.

Fall for these Winston-Salem events

Cooler temperatures bring literature, fiesta, fashion, food, and one of the top arts & crafts festivals to the Mid Atlantic.

September Bookmarks Festival of Books & Authors: Meet your favorite authors, add to your literary collection and meet publishers and other vendors while filling up at the food trucks.

The month also brings the Hispanic League Fiesta, a free street festival celebrating diversity, Hispanic heritage, and cross-cultural understanding. This one-day event is the largest street festival in the Triad, drawing over 20,000 attendees.

Rounding out the calendar is Winston-Salem Fashion Week. Since 2015, WSFW has presented emerging designers from the Triad and surrounding areas as well as New York, Atlanta, and Washington DC. 

OctoberCarolina Classic Fair: This agricultural fair averages 325,000 each year. For 10 days, visitors enjoy a world-class carnival, nationally known musical entertainment, a midway full of food and exhibits of livestock, poultry, fine arts, and crafts. 

Fall also brings October’s Winston-Salem Food Truck Festival. Downtown sets the stage for food trucks from all across North Carolina. Sample them all while enjoying live music and your favorite adult beverage.

NovemberPiedmont Craftsmen Fair: Held at the Benton Convention Center, this two-day fair features over 100 fine artisans from across the US. Here you’ll find one-of-a-kind works for your home – or for someone special on your holiday gift list.

These are just a few great Winston-Salem annual events. Learn more about what the area has to offer with our Insider’s Guide. And if you need accommodations, here’s a lineup of downtown hotels.

Whatever the time of year, Millennium Center is the perfect place for your Winston-Salem wedding, special occasion or corporate event. Contact us to discuss your event and to schedule a tour

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