Downtown W-S to host several festivals

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.

Winston-Salem Open

Aug. 21-28, 2021

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Come to Winston-Salem and create a racquet in honor of the Winston-Salem Open’s10th anniversary. Center court action takes place Aug. 21-28 and boasts full capacity and full prize money.

“Our tournament this August promises to be a thrilling event for fans and will feature some of the best professional tennis players from around the world,” says Jeff Ryan, Winston-Salem Open tournament director. “The tournament will also include a number of rising American players.”

Previous players include Sam Querry, Steve Johnson, Pablo Carreno Busta, Jurgen Melzer and John Isner, a North Carolina native who has won the WSO twice. The Open is held at the Wake Forest Tennis Complex adjacent to Truist Field.

Just minutes from the tennis courts is the Reynolda Mile, where out-of-towners can experience a glimpse into the life of the Reynolds family, one of Winston-Salem’s most revered couples. The estate of R.J. and Katharine Reynolds, the Reynolda House Museum of American Art, is located at the center of Reynolda’s 180 acres and considered a rare gem among the nation’s cultural institutions and historic green spaces. The museum presents a renowned art collection in a historic and incomparable setting: the original 1917 interiors of the country manor.

A 10-minute drive from the tennis action is the Historic Brookstown Inn, the perfect place to lay your head after a night of watching people get served. The Inn has a special hotel package that includes two tickets to either the 3 or 7 p.m. tournament match.


Sept. 11, 2021

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Lighting the path toward multicultural understanding is Winston-Salem’s Hispanic League — and their annual street festival, FIESTA, brings thousands of visitors together each year in an effort to achieve that initiative.

As one of downtown Winston-Salem’s largest annual street festivals, FIESTA promises an experience like no other. The Parade of Flags greets the crowd upon entrance, hyping up attendees while the sounds of Latin music drift down the street and the aroma of Latin food wafts through the air.

This year, in addition to music and food, there will be arts and crafts, a children’s area, and the annual dance competition. The event takes place on Sept. 11.

If your feet are tired after dancing the day away, there’s several lodging options available, all within walking distance. The rooftop bar found in the Courtyard by Marriott Winston-Salem Downtown, Top of Fourth, is a great place to put your feet up while still feeling like you haven’t turned in for the night.

Bookmarks Festival of Books & Authors

Sept. 23-26, 2021

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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.

At the 2019 festival, Bookmarks, Winston-Salem’s only nonprofit bookstore and literary arts organization, attracting more than 20,000 readers and hosting more than 50 authors and illustrators.

Visits from national and international best-selling authors is the highlight of Bookmarks’ Festival of Books & Authors, as well as appearances by state and local authors, kids’ authors, and the vendor fair lining the streets of downtown Winston-Salem. Seminars and panel discussions are also held throughout the event at various walkable locations.

“Bookmarks is thrilled to celebrate our 16th anniversary festival in a hybrid format this year,” says Jamie Rogers Southern, executive director of Bookmarks. “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.”

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 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.

Additional events related to the festival and event updates will be released throughout the summer.

Winston-Salem Cycling Classic

Sept. 24-26, 2021

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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.

Gears & Guitars

Sept. 24-26, 2021

Facebook: @gearsandguitars

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 Winston-Salem’s Innovation Quarter, Gears & Guitars is an outdoor concert series held in conjunction with the Winston-Salem Cycling Classic (see below for more information). Music lovers gather at Bailey Park for nightly concerts with nationally-recognized recording artists.

This year’s lineup is still being finalized but judging from prior years, it’s sure to wow.

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.

For more on upcoming events and festivals, visit here. For hotel and lodging amenities, visit here.