The 37th annual Madison Juneteenth will take place Saturday, June 20, 11 a.m.-5 p.m. at Penn Park on Madison’s South Side. This year’s theme is “Black Resilience: Celebrating Our History and Presence,” and will commemorate the 160th anniversary of Juneteenth.
Madison’s longest-running Juneteenth celebration is once again being organized by Annie Weatherby-Flowers, the longtime chair of Madison’s Juneteenth Day celebration. This will be her 37th year in that role. Weatherby-Flowers fondly remembers helping to start Juneteenth here in Madison back in 1990.
“When I grew up in Milwaukee, Juneteenth was always like homecoming. Folks who went off to college, they were back. You had the collective. You have people from different areas and different backgrounds all in the same place, all enjoying each other and sharing the same food, culture, and community,” Weatherby-Flowers tells Madison365. “When I first moved to Madison from Milwaukee, it was such a different environment here. If you didn’t belong to a sorority or fraternity or a certain church, there was no sense of collective community.
“I remember thinking, ‘We need to organize a Juneteenth here in Madison.’ That was a conversation over lunch,” she adds. “And 37 years later, here we are.”
Since 1990, Madison’s annual Juneteenth Celebration at Penn Park, 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.
“I still see many people at Juneteenth from those very first years,” Weatherby-Flowers says.
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.
“We are excited to come together collectively to have a space where there’s nothing but pride and showcasing all of the wonderful things and all the contributions that we have made, not only in the United States, but in the world,” Weatherby-Flowers says. “This is such an important day. We all benefit from a collective celebration of the hopes and dreams of the slaves and the people who marched to make a change and to get these basic rights for people in America throughout our history.
“Our overarching theme is Harambee, which is Swahili for ‘pulling together,’ and so that has always been the fundamental process … pulling together,” she adds. “We will be celebrating the resilience in Black communities across the nation.”
The Juneteenth Parade will kick off the Madison Juneteenth event this year, as it does every year, starting at the Labor Temple and making its way down Park Street to Penn Park.
(Photo by A. David Dahmer)
“We will have a Juneteenth band, we have our youth area, the church area, the teen area, and some of the things and some of the programming that we have done before,” Weatherby Flowers says. “We will have local community groups and our local vendors, so it’ll be similar, but it’ll be a little bit more condensed than usual because of budgets.”
Juneteenth is hosted by Kujichagulia Madison Center for Self-Determination, a nonprofit organization founded by Weatherby-Flowers and Winston that works to unite Madison-area African American communities to address collective issues affecting certain sectors of the community.
(Photo by A. David Dahmer)
This Juneteenth is important, Weatherby-Flowers says, because this year marks the 100th anniversary of Black History Month, but it also comes at a time when equity and DEI initiatives are under attack.
“When we look at the Voting Rights Act, we look at the Civil Rights Act, we look at the DEI being attacked and dismantled … The University of Wisconsin DDEEA [Division of Diversity, Equity & Educational Achievement] was a $10,000 sponsor [of Madison Juneteenth], and it no longer exists, for example,” Weatherby-Flowers says. “I think that when Juneteenth began, it was put on by the community. People brought food, people entertained, and they celebrated in a different way. As it grew and became more profitable, sponsorships and things like that became very important, because it requires a lot to put this big celebration together.
“The political climate has turned and all these programs are losing funding and existence and the money that was going to all of us and those programs is no longer there. We’ve lost quite a bit of money (due to anti-DEI initiatives) and have to fill the holes,” she adds. “It’s been a challenge. It’s been sad to see that the feeling of equality and equity and access to political systems are no longer there,” she adds.
Despite those budget restrictions, Weatherby-Flowers is confident people will have a great time at Madison Juneteenth 2026. “This Juneteenth Celebration will be nice because I don’t try to do anything that’s not nice, because my mother always said, ‘If a task is once begun, never leave it till it’s done. Be the labor great or small, do it well or not at all.’”
However, after 37 years, this could be the last one that Weatherby-Flowers will be organizing.
“I’m trying to hand it off to some younger folks. We’ve been talking about this for a couple of years,” she says. “I’m not sure if young people think collectively like we have in the past and I think that’s been the biggest obstacle as I look to hand this off to the younger generation. My physical health is dictating that I let it go and maybe just be an advisor. I would love to see people from the younger generations take this over.”
Juneteenth celebrations have been popping up everywhere since it became a national holiday, including a few more in Dane County. “That competition for funding has impacted our celebration greatly. But the Madison Juneteenth will always be the original Juneteenth,” Weatherby-Flowers smiles.
“We always need and appreciate volunteers for Juneteenth,” she adds. “It’s a great event.”
To volunteer for Juneteenth Madison 2026, click here.
