Juneteenth in Winston-Salem: The Evolution of a City’s Freedom Celebration

10 minute read

There is a deep-rooted connection between Cheryl Harry and the community she was born and raised in. She witnessed Winston-Salem’s transformational journey from segregation to the Civil Rights era to today, where she’s a community leader and catalyst for the city’s annual Juneteenth celebration.

For Harry, Juneteenth in Winston-Salem is more than a celebration; it’s a way of preserving a deeply important–and personal–history. 

Behind the scenes, Harry, the founder of Triad Cultural Arts, Inc. has established–and reestablished–the local Juneteenth event that this year will celebrate 160 years of African American freedom in America.

Winston-Salem’s Juneteenth celebrations join communities in surrounding areas and across the nation to honor the federal holiday, which memorializes the day in 1865 when Union soldiers announced and enforced that all people were free in Galveston, Texas. Galveston was the last community in the U.S. to officially abolish slavery, which is why the holiday is often referred to as Freedom Day.

While Juneteenth only began to be recognized as a federal holiday in 2021, Winston-Salem has been celebrating that history for a lot longer. Officially, the local celebration dates back 26 years, though Harry remembers an even earlier beginning.

This year’s Juneteenth celebration will be the tenth hosted in the iQ, and that partnership–and the event itself–were born from Harry’s passion for remembering and celebrating Winston-Salem’s unique story within Black history.

Cheryl Harry is the keeper of the Juneteenth Celebration in Winston-Salem
Cheryl Harry, Founder of Triad Cultural Arts, Inc.

Juneteenth Through a Local Lens

Harry has been a driving force in celebrating Black history in Winston-Salem for decades, which has a very well-kept and storied legacy. She’s been a part of the Juneteenth celebrations from the very beginning.

For many community members, Winston-Salem’s Juneteenth celebrations in 2005 and 2006 were the first community Freedom Day events they remember. These celebrations attracted a great deal of attention as the famous poet, writer, Civil Rights activist, and Wake Forest University professor, Maya Angelou participated as a guest speaker.

These first two festivals were planned by the Juneteenth Festival Committee, which included Harry, with the support of the City of Winston-Salem’s Human Relations Department. This committee was the preamble to Harry starting the Triad Cultural Arts organization in 2007, which still plans the Juneteenth event along with other experiences that aim to preserve, interpret, and exhibit the heritage of Black Americans.

According to Harry, the celebrations of Juneteenth in Winston-Salem in the mid-2000s were a resurgence of community celebrations (highlights pictured below). The actual inaugural community event was held in the late ‘90s. At the time, Harry was working at the YMCA developing community programs, and local storyteller, Pat “Mardia” Stepney, introduced the idea of hosting a Juneteenth festival. 

“We were in a recap meeting after a Kwanzaa event, and it was the first time I’d ever heard the story about the people in Galveston,” Harry says. 

The YMCA held the community’s first Juneteenth celebration in 1999 behind the YMCA on Waterworks Road.

What Harry remembered the most about that first event was the important role the vendors played in the event. They elevated authentic African culture with artisan crafts and apparel. 

“We had storytellers, music, and all kinds of Afrocentric art and accessories,” Harry says. “I think that’s what made it special because you witnessed the celebration and appreciation for African culture through these items.”

At one of these Juneteenth celebrations, Harry even bought a carved Sankofa bird, which became part of the inspiration for the Triad Cultural Arts logo.

The festival continued for years, but stopped after Harry and other staff members left the YMCA. Harry eventually assembled grassroots community members to form the Juneteenth Festival Committee, which reestablished the festival that led to what the community now enjoys at the annual Juneteenth celebration. 

The Legacy Under Our Feet

In order to better preserve and communicate local Black history, Harry founded the Triad Cultural Arts, which solidified the Juneteenth festival, as well as promoted other cultural events to preserve history in Winston-Salem for years to come.

For the Juneteenth festival, Harry continued to incorporate more and more local history each year, like instituting an event that celebrated the day African Americans in the Town of Salem first heard their freedom announced.

St. Philips Moravian Church, Pictured center. Photograph by Henry Lineback, ca. 1866. Collection of Old Salem Museums & Gardens.

On May 21, 1865, the Union cavalry gathered into St. Philips Moravian Church, the oldest African American church still standing in North Carolina, to proclaim all persons were free. Triad Cultural Arts added an event to its Freedom Day celebrations that is hosted at the church–which still has pews from the famed moment–on or around the 21st of May each year to commemorate the announcement. The local story keeps the recent national movement much closer to home. 

However, the larger celebration in June was hosted in a variety of locations around Winston-Salem until the Triad Cultural Arts Alliance relocated the Juneteenth celebration to the Innovation Quarter. The change of venue came about when Harry attended a meeting for another purpose in the Wake Forest Biotech Place building. She looked around and thought it would make a great venue for the event. 

Juneteenth in the Innovation Quarter in Winston-Salem

“Our celebration feels perfectly placed here,” Harry says.  

Harry wasn’t sure how the idea would be received, but Lindsey Schwab, the director of community relations for the iQ, was enthusiastic about the idea.

“When Cheryl brought us the idea of hosting Juneteenth in the iQ, we were thrilled,” Schwab says. “It was an amazing chance to connect to and honor the history that took place in the former tobacco district.” 

Juneteenth in Winston-Salem had a new home. The location in the iQ was an enhancement—having both an inside space and an outdoor stage—and attendees loved it. 

Over the years, the event grew in the iQ. The first year, attendance eclipsed 3,000 attendees. Last year, during the 25th anniversary of the local celebration, organizers entertained more than 12,000 people. Even with the location proving good for future growth, for Harry, there was more than a physical uplift to the event–there was a spiritual one as well. 

“When I saw the people in [Bailey Park], it looked like they were supposed to be there,” Harry says, “but more than that, it was like our ancestors were with them—like we were our ancestors’ dreams.”

Harry’s reasons for choosing the iQ as the new home of the Winston-Salem Juneteenth celebration weren’t just because of the amenities and space it offered, but also the innovation district’s connection to local Black history.

While that history may not be as widely known as the tobacco to technology story many know about the district, a mural on Seventh Street in the northern part of the district highlights what once was a mecca for Black businesses in Winston-Salem. The legacy under the feet of festival participants are the streets, sidewalks, and land where Black businesses and communities thrived around the R.J. Reynolds Tobacco Company. 

Harry remembers riding the Safe Bus, which operated out of what is now the iQ, with her grandmother as well as spaces where Black residents could shop, gather, and be served with respect, even as Jim Crow laws denied them equal rights elsewhere. The echoes of that resilience still linger in the repurposed tobacco warehouses and revitalized streets.

Mural located on Seventh St. honoring the former Black business district

“The richness of this [former] community provided a sense of security,” Harry says. 

By hosting Juneteenth in the historic tobacco district, the festival is not only a celebration of emancipation in 1865, but also a tribute to those who endured, built, and believed in a better future for their community throughout the nineteenth and twentieth centuries.

The Keeper of History

Harry has been the driver behind many of the additions to Juneteenth in Winston-Salem, understanding the significance of hosting the festival in the historic tobacco district and the importance of recognizing Winston-Salem’s local Freedom Day.  

Normally, those connections are realized by a historian or archivist. Harry isn’t either, at least not by trade, but she recognizes the importance of collecting, organizing, and sharing information. She attributes her contributions to preserving Winston-Salem’s local history to passion. 

“Preserving and teaching history seemed to find me,” Harry says.

The Winston-Salem native holds a wealth of community knowledge through her own lived experience. Harry’s work experience also exposed her to historical research and presented opportunities to distribute that knowledge to her community. One of the roles that brought her closer to Black history in this area is serving as cultural curator and director of African American programs at Old Salem Museum and Gardens.

“That’s when I really got into the history,” says Harry. “As I learned more from the pristine records kept at the museum, I thought to myself, ‘Why don’t we know this as Black people in Winston-Salem?’”

Celebrating Juneteenth in Winston-Salem

Everything she learned about African Americans while curating content or programs at Old Salem, Harry implements into Triad Cultural Arts’ events not only to enhance Black culture, but also to equip the community with valuable knowledge. It is why the May 21st event was introduced to the Freedom Day festivities, instilling local history into Juneteenth.

“I remember the thriving businesses, the Safe Bus, Mrs. McClean’s business school, doctors’ offices, and the Model Pharmacy. I just have the memories of being there,” says Harry. And she’s made it her mission to tell the stories and pass on the essence of Black history through events like the Juneteenth Celebration.

Be a Part of Juneteenth in Winston-Salem 

Triad Cultural Arts is set to host its 26th Juneteenth Celebration on Saturday, June 21 from 12:30 to 8 p.m. in the iQ. Hosting the day’s festivities is Kara Peters of WXII News and Triad-native entertainer B-DAHT. The celebration takes place on Bailey Park’s main and upper-level stages, as well as in the Wake Forest Biotech Place Atrium, for a day of culture, creativity, and fun.

Rich history of the Junteenth Celebration in Winston-Salem

Get ready for a celebration packed with nonstop entertainment across three stages. From the soul-stirring rhythms of African drumming and the powerful voices of the Piney Grove Mass Choir to R&B, hip-hop, and line dancing, there’s a musical style for everyone. Watch the McIntosh County Shouters bring history to life, sway to smooth jazz performances from Janice Price, Cle Thompson, and Diana Tuffin, and experience the artistry of spoken word led by LB the Poet and E’laina Barron. 

“The Juneteenth celebration is one of our favorite celebrations,” Lindsey Schwab says. “It brings a vibrant energy to the iQ, and this year, we’re looking forward to how Triad Cultural Arts is incorporating even more local history into the event.”

This year, Triad Cultural Arts is adding a Black Joy Street Procession, starting at 11:30 a.m. It is a walk of freedom beginning on Martin Luther King Jr. Drive, leading to the huge community celebration in Bailey Park.

Before the annual community bash, Triad Cultural Arts observes June 19 with two other events, including flash mobs throughout the day in Forsyth County. Then, in partnership with the Town of Kernersville, a Juneteenth celebration with fireworks and drones will be held in Harmon Park later that evening at 6:30 p.m.

Juneteenth in Winston-Salem

To learn more about this year’s Juneteenth celebration and the Black History of Winston-Salem, visit Triad Cultural Arts. You can also learn more about the Black History of the historic tobacco district on the iQ website. 

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