The fourth annual Homewood-Flossmoor Juneteeth Festival on Saturday, June 15, will include some new features, entertainment, art, more food than ever and the return of many favorite activities.
Youth leadership and empowerment organization You Matter 2 will operate what organization officials say is the biggest Juneteenth celebration in the South Suburbs.


Juneteenth marks the day, June 19, 1865, when Union troops arrived in Galveston, Texas, to inform the enslaved people there that they were free. That moment was long celebrated by Black communities, but in recent years has gained a mainstream following.
Juneteenth marks the day, June 19, 1865, when Union troops arrived in Galveston, Texas, to inform the enslaved people there that they were free. That moment was long celebrated by Black communities, but in recent years has gained a mainstream following.
Juneteenth was recognized as a paid holiday in Cook County in 2020, as a federal holiday in 2021 and as a state holiday in 2022.
In addition to music, art, history, kids activities and food, the event will feature hundreds of area Black-owned business vendors.
The festival from 11 a.m. to 6:30 p.m. will be held in the south parking lot of Homewood-Flossmoor High School, 999 Kedzie Ave.
There will be three big changes this year, two of which were made necessary by the festival’s size and popularity, according to You Matter 2 founder and CEO Destiny Watson.
One is the addition of off-site parking. The festival takes up all of the H-F High south parking lot, and most of the north lot is needed for vendor parking. Additional parking will be available at two nearby churches, All Nations Community Church, 18620 Kedzie Ave., and Woodlands Community Church, 18301 Governors Highway.
Shuttle buses will run regularly throughout the day.
There will also be an admission charge for the first time, $5 for children from age 3 to 17 and $10 for adults age 17 and up.
You Matter 2 founder and CEO Destiny Watson said the fee is necessary to account for rising costs of putting on the large event and the need to support the organization’s year-round work.
“We have to find ways as a small nonprofit that’s been growing to be able to pour back into our organization and ensure that we can still operate beyond Juneteenth,” she said.
You Matter 2, founded in 2014, creates programs throughout the year to support youth leadership and personal growth.
Watson said some large festivals in the region have succumbed to cost increases. Hyde Park Summer Fest, for example, would have celebrated its 10th anniversary this year but closed because of high security costs.
“We don’t want to charge astronomical prices, but there has to be that type of community support there as well,” she said, noting that vendor fees, merchandise sales and sponsorships no longer bring in enough revenue.
Tickets are on sale for the children’s activities, which include a zip line, Toxic Meltdown, musical chair swing and soft play area. The cost is $30 for unlimited play when purchased in advance or $35 on the day of the festival.
H-F High alumnus Abe Ilo and the Annie Lee Art Foundation will return. Ilo’s art was featured in a gallery at the festival in 2023.
The festival will feature artist JessTimeless. She will set up a mural that folks at the festival can help create.
“I dabble in anything and everything when it comes to art,” she said, noting that she does everything from face painting to curating exhibits to teaching art in Chicago Public Schools. “I will be supplying free sketch boards. You can come out, feel free to paint on it.”
“Ferguson Voices” also will return. The exhibit displays excerpts from interviews following the police killing of Michael Brown in 2014.
Entertainment this year will include returning favorites like the Jesse White Tumblers and the 40+ Double Dutch Club plus the Fieldcrest School of Performing Arts, Genxsis Step Team. There will be 14 performing acts throughout the day plus other activities, including an African drum circle.
Another new feature will be a beer and wine garden in the food court with three vendors, Tapville Mobile Taproom, Vintrendi Wine Company and Moor’s Brewing Company.
The food options will expand, too, with 32% more vendors than last year.
The Juneteenth parade on Wednesday, June 19, marks the 159th anniversary of the news of emancipation reaching Galveston. The plan is similar to last year’s event. It will start at 9 a.m. at Western Avenue School, 940 Western Ave. in Flossmoor.
The parade route will head south on Brassie Avenue, then west on Flossmoor Road to the Parker Junior High parking lot.
The parade typically includes marchers, dancers and steppers performing along the route. Organizers invite spectators to line Flossmoor Road to watch the parade pass by.