There’s always a reason to hit the road and head to Winston-Salem – especially with its more than 100 downtown restaurants and 5,000 hotel rooms – and the upcoming slate of end-of-summer events and festivals is more than reason enough to visit.
Sept. 10, 2021
Lighting the path toward multicultural understanding is Winston-Salem’s Hispanic League — and their annual street festival, FIESTA, traditionally brings thousands of visitors together each year in an effort to achieve that initiative. In light of the pandemic, FIESTA 2021 has been reimagined as an outdoor drive-in concert with live Latin music and folkloric dancing.
The Fiesta: Concert Under the Stars takes place Friday, Sept. 10 from 5:30 – 10:30 p.m. at the Winston-Salem Fairgrounds and features a slew of family-friendly entertainment including West End Mambo, Los Acoustic Guys, and Ballet Folklorico Corazón De Mexico. Serving up authentic Latin cuisine, food trucks will be onsite throughout the evening’s festivities.
View the entertainment schedule here.
Sept. 23-26, 2021
Nowhere else in the country can you find a festival dedicated to everything book-related. The largest annual book festival in the Carolinas, Bookmarks’ Festival of Books & Authors attracts thousands of bibliophiles each year.
This year’s hybrid event (both in-person and virtual) will be held Saturday, Sept. 25. Virtual events will begin on Thursday, Sept. 23. Fifty authors will be in attendance for in-person events, and 14 authors will participate virtually during the 2021 Festival of Books & Authors.
“Bookmarks is thrilled to celebrate our 16th anniversary festival in a hybrid format this year. In-person events will take place downtown in six venues including and surrounding Bookmarks’ retail location, and pre-recorded virtual events will be streamed simultaneously as part of the festival program.”
– Jamie Rogers Southern, executive director of Bookmarks
The street festival will feature community exhibitors and food trucks, along with most of the author programming. Authors from around the country will speak on topics as varied as podcasting to using storytelling as a life skill, and genres from horror to romance.
Located in the heart of downtown on Fourth Street, Bookmarks—Winston-Salem’s only nonprofit bookstore and literary arts organization—is surrounded by hotels and restaurants to make your overnight stay easier. A two-night stay at the Historic Brookstown Inn includes a $50 Bookmarks gift certificate, two food truck vouchers, and loads of festival goodies. A special festival rate is also available at the Kimpton Cardinal Hotel.
For a complete list of participating authors, featured books, special events, and festival locations, click here.
Sept. 24-26, 2021
While the sidewalks and parks are full of activity the weekend of Sept. 23, certain Winston-Salem trails and roads will also be abuzz with the sound of cycling as the annual Winston-Salem Cycling Classic fills the streets.
For three days straight, Sept. 24-26, cyclists race for first place in a variety of events including the 2021 USA Crit Series Criterium Challenge for both men and women and the Winston-Salem Cycling International Criterium Challenge. Opportunities to meet some cycling pros will be abundant throughout the weekend.
The races aren’t only for professionals, either. Several amateur events will be held including a veterans ride, a community bike ride that highlights much of Winston-Salem’s urban and rural scenery. All of the events will surround downtown’s Bailey Park and the Gears & Guitars performances. Registration for all Winston-Salem Cycling Classic events is now open.
The nearby Embassy Suites by Hilton Winston-Salem has an indoor pool for you to cool off and Small Batch Brewing, stop no. two on our Craft Draft Beer Crawl, is mere steps away. Grab a lager and burger and beat the heat.
For more on how easy it is to bike around Winston-Salem, check out our blog.
Sept. 24-26, 2021
The bass in Bailey Park will be bumping this Sept. 24-26 as Winston-Salem welcomes back Gears & Guitars, the south’s biggest party on two wheels, for their fifth annual event.
Hosted in Innovation Quarter, Gears & Guitars is an outdoor concert series held in conjunction with the Winston-Salem Cycling Classic. Music lovers will gather for three days of back-to-back live music. This year’s line-up features Grace Potter and Hannah Wicklund on Friday, Sept. 24; Gov’t Mule, Devon Gilfillian, and Ida Mae on Saturday, Sept. 25.; and The Smithereens, Fastball, and Magnolia Green on Sunday, Sept. 26. Individual concert tickets and 3-day tickets are available to purchase online, and tickets will be available at Bailey Park on the day of each respective concert.
Plan your trip now and book a stay at nearby Hampton Inn & Suites Downtown or the Kimpton Cardinal Hotel, both of which will serve a breakfast that’ll deliver that morning kickstart needed after a long night out on the town.