This year, 2025, commemorates the 160th anniversary of Juneteenth, a defining moment in American history and a representation of freedom, resilience, and the never-ending journey toward justice.
Here in Madison, organizers are excited about that anniversary as they prepare to celebrate the 36th annual Madison Juneteenth, led by Annie Weatherby-Flowers, the longtime chair of Madison’s Juneteenth Day celebration, who describes this year’s celebration as “bittersweet.”
(Photo by A. David Dahmer)
“In a way, it is very exciting … the 160th anniversary. But we’re also being confronted by the new Jim Crow mentality in America right now in the political system,” Weatherby-Flowers tells Madison365. “So with some of our bigger sponsors, like UW [University of Wisconsin], the funds are being attacked and people are being laid off, and some of the funding has been cut in terms of DEI across the country, affecting the funding for Juneteenth that we get from some of our biggest sponsors.”
Juneteenth commemorates June 19, 1865, a day when African-American slaves in Texas were told by Union forces that they were free. They were the final group of slaves to realize their freedom. Deep in the Confederacy, they were unaware of the signing of the Emancipation Proclamation almost two years earlier. A celebration of the day has been held annually in Texas ever since, which eventually spread to other states.
Since 1990, Madison’s annual Juneteenth Celebration at Penn Park, which was co-founded by Weatherby-Flowers and Mona Adams Winston, has been a fun, family-friendly celebration of the lived experiences and accomplishments of Black Americans historically and presently here in Madison and across the nation.
“We are going to kick off the celebration this year with the [Juneteenth] flag-raising as we do every year,” Weatherby-Flowers says. “We will have a book talk with Dr. Chuck Taylor, who has a new book [“Juneteenth: The Promise of Freedom”]. He will be hosting the event at the [Black Business] Hub.
“We’re looking at doing a celebration from June 19th to the 21st. The annual Juneteenth parade will be followed by the outdoor celebration and we’re targeting the 21st,” she adds. “On the 19th, we’re looking to do a gala with food and awards and entertainment.”
This year’s event will once again be hosted by Kujichagulia Madison Center for Self-Determination, a non-profit organization founded by Weatherby-Flowers and Winston that works to unite Madison-area African American communities to address the collective issues that affect certain sectors of its community.
“Our theme for this year is black resilience, and collectively, we will still rise in response to the attack and the new Jim Crow kind of stance that the political machine is launching in our country right now,” Weatherby-Flowers says. “We will be really focusing on the education of life after the emancipation, so [things like] the establishment and history of the Urban League, the history of the Divine Nine, the history of the black nations, and some of those historical institutions that spun out of slavery.
“We will really focus on the historical pattern of African American accomplishments and even challenges,” she continues. “So a lot of our educational sessions will be about some of those historical initiatives that are present today. We really want to connect the past to the present to let folks know that we’re not new to this rodeo. And how do we collectively pull together to really move forward?”
Janine Stephens Hale, the new Chief Administrative Officer (CAO) of The Center for Black Excellence and Culture, is coming back to help plan Juneteenth, Weatherby-Flowers says, and maybe to help “transition the organization of the celebration to the Center for Black Excellence.”
Weatherby-Flowers adds that after 36 years, this year will be the last as the lead organizer.
“Physically, I have a lot of stuff going on and it’s time for me to do something different with my life,” she says. “I’m not 100 percent sure at this point, but part of me does not want to let my baby go, but another part of me knows that it is time.”
Juneteenth has always been a very important day for Weatherby-Flowers, who grew up and lived in Milwaukee before she moved to Madison in 1989.
“I have fond memories of Juneteenth in Milwaukee … It’s when school was out and you would see the college students. There’s music. There’s food. There’s Gospel. There’s education,” she says. “It was just a great opportunity to be around people and hang out and eat roasted corn. It was like a coming together, like a big homecoming for different communities to converge.”
For Weatherby-Flowers, it also signified the beginning of summer in Milwaukee. “It was before Summerfest and before Kool Jazz Festival … those sorts of things. It was a wonderful opportunity to see people you maybe haven’t seen in a while,” she says. “The older I got, the better it became to me in terms of the significance of what it was … watching the parade, coming together as friends. For my youngest son, it was his first event watching Juneteenth in 1978.”
Weatherby-Flowers adds that it gives her joy “to see different generations come together at Juneteenth.”
“Now I’m seeing my grandkids with kids, with their children at Juneteenth. When we started Juneteenth, my boys were pre-teen and a teenager,” she says. “Now one is a grandfather. It’s really special to have the generations together in one space.
“Particularly now that we have become more individualized. We do things more on social media and less in person together,” she adds. “So Juneteenth is significant to come together collectively and celebrate the past, present and the future, because that’s what Juneteenth really is about.”
Weatherby-Flowers encourages people to check out the Juneteenth Facebook page to get more involved. Juneteenth is still looking for donations, sponsors, vendors and artists to perform.
“We really want to celebrate the 160th anniversary of Juneteenth, but we do have limited resources,” Weatherby-Flowers says. “Significant contributions and sponsorships are needed now more than ever.
“And if people reading this article have talents or food, or they want to contribute or volunteer, please contact us,” Weatherby-Flowers says. “There’s really no event like this in Madison. It’s one of the best.”
