Break out your calendar, Winstonians and say goodbye to FOMO because we’ve got you covered with some of the biggest events happening this year.
Note: Some major events don’t have a set date yet, but also keep in mind some set dates are subject to change.
The Clash at Bowman Gray Stadium | Feb. 1-2 | Get ready for an adrenaline-fueled weekend as you watch NASCAR’s top athletes compete for the top spot. Pro tip: Parking is limited, so make sure to arrive early to grab a spot. Watch the weekend schedule here.
Face to Face Speaker Forum: John Legend | Apr. 8 | The multiplatinum singer-songwriter will share how he rose in the entertainment industry from a young age. Pro tip: Buy your ticket ahead before it sells out.
RiverRun International Film Festival | Apr. 11-19 | Calling all cinema lovers — meet + network with other cinephiles from around the world and watch special screenings, premieres, and programs.
Piedmont Earth Day Fair | Apr. 26 | The biggest earth day fair in NC will return to the Winston-Salem Fairgrounds with environmental exhibits, live performances, and more. This educational event is perfect for the family.
Gears & Guitars | May 23-24 | The 12th annual cycling weekend event features professional + amateur cycling, community bike rides, and free outdoor concerts. Pro tip: Stay tuned to see who the next big headliner will be.
Pride Festival | June 14 | This community celebration will include a parade and food for purchase from food truck vendors.
Triad Cultural Arts Juneteenth Festival | June 21 | Experience a vibrant array of Afrocentric cultural exhibits, culinary selections, and merchandise in commemoration of 160 years of freedom.
1Love Festival | June 26-28 | The two-day celebration of peace features international and local musicians, filmmakers, poets, thought and faith leaders — so get ready for soulful melodies + uplifting performances.
Winston-Salem Open | Aug. 16-23 | Watch world top tennis players compete for the No. 1 spot on the courts before they advance to the US Open.
Historic Bethabara Apple Festival | September | Explore history with 18th-century craftsmen, bring the kids to play colonial games and enjoy face painting, plus shop a multitude of apples from local vendors.
Bookmarks Festival | Sept. 25-28 | Meet authors you know and love or discover new ones. Attend Q+A’s, workshops, book signings, and more.
Fiesta! | Sept. 20 | Get ready to party at one of the Triad’s largest cultural festivals and take part in arts and crafts activities, shop food from Latin America and watch colorful dance performances.
Winston-Salem Fashion Week | Sept. 25-28 | From runway shows to designer’s meet ups, this week-long event showcases a wide range of daily wear, urban street style, and formal wears.
Eat. Drink. Triad. Restaurant Week | TBD | Celebrate local cuisine across the Triad this October. You can shop at participating restaurants at a discounted price and discover your new favorite eats.
Carolina Classic Fair | Oct. 3-12 | There’s no better place for carnival rides, competitions, games or to try out new innovative foods than this annual fall fair.
Tanglewood Park Festival of Lights | Nov. 14-Jan. 1, 2026 | Stroll through a five-mile journey, watching dazzling light displays and installations which attracts over 300,000 visitors on average every year.
The Nutcracker | December | The cherished holiday tradition wows thousands of attendees every year with a captivating choreography performed by students artists. Watch the whimsical winter performance at the Steven Tanger Center in Greensboro while the Stevens Center undergoes renovations.
Piedmont Craftsmen’s Fair | November | Shop quality handworks from more than 100 fine artisans from across the country.
Small Business Saturday | Nov. 30 | Support Winston-Salem’s small businesses by shopping local during the nationwide event. Follow @downtownwinstonsalem to see which local business is offering a special discount that weekend.
Winston-Salem Holiday Parade | Dec. 6 | Watch bands and community groups march downtown celebrating different religious holidays. Plus, end the night with the annual tree lighting at Corpening Plaza.
Bookmark this article and see just how many events you can attend in the Twin City this year. Did we miss one? Drop us a line for a chance to be included.