18 Favorite Annual Winston-Salem Events
Here’s our guide to 18 favorite annual Winston-Salem events. Discover North Carolina history, culture, food, and other unique experiences. Make sure you add your favorites to your 2025 calendar.
December events in Winston-Salem
Whether it’s holiday cheer, chocolates or fine crafts, Winston-Salem is ready for locals and visitors in December. 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: Find Christmas-themed historic house tours, caroling, and family-friendly activities on the 170 acres that comprise the Reynolda House Museum of American Art, Reynolda Gardens, and Reynolda Village.
Holidays at Old Salem: Take a stroll 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 isn’t complete without this classic ballet. It features UNCSA student 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 2025 with a foot race through the lights at midnight on New Year’s Eve.
And speaking of New Years Eve …
Millennium Center’s New Year’s Dance Party: Looking to raise the bar on your New Year’s celebration? Dance into 2025 with us! Complimentary champagne toast and breakfast. Cash bar. General admission and VIP tables. Get your tickets here.
Winter annual events to cheer you up
Don’t let winter get your down. Start the year with a run for a good cause and enjoy two of life’s favorite things – chocolate and wine!
January – Miles for HOPE: Each year Justin Bailey runs the number of miles that correspond with his birthday to raise funds for local charity Help Our People Eat. Choose from a 5K, 10K, or 1 mile run to raise money and awareness – or go the full distance with Justin!
February – Greensboro Wine & Chocolate Festival: Just over in nearby Greensboro, you can celebrate great wines and chocolates from North Carolina. Take some home to enjoy by the fire.
Celebrate Spring events in Winston-Salem
Spring kicks off in Winston-Salem with beautiful botanical garden blooms, then a well-regarded film festival, the largest Earth Day Celebration in NC and wraps up with the biggest party on two wheels.
March – Paul 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.
April – RiverRun 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, celebrate the Piedmont Earth Day , 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 offer African American culture and Sci-Fi events, while the city plays host to world class tennis in August.
June – Juneteenth 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. 
July – ConGregate: This is a completely volunteer-run, interactive science fiction convention. For the Sci-Fi fan, it’s more than just an exhibit hall – it’s total immersion.
August – Winston-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, fiestas, and a classic fair with rides and a midway. And be sure to start your Christmas shopping with the one of the Mid-Atlantic’s most renowned artisan craft shows and sales.
September – Bookmarks Festival of Books & Authors: Meet your favorite authors, add to your literary collection, and converse with publishers 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.
October – Carolina Classic Fair: For 10 days, over 300,000 visitors enjoy a world-class carnival, nationally known musical entertainment, a midway full of food and exhibits of livestock, poultry, fine arts, and crafts.
November – Piedmont 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.
