One of Julian Walters’ fondest childhood memories of Juneteenth is the early summer mornings he spent getting ready for the local parade on Madison’s south side. Each year, he dressed up as a Black trailblazer, like Martin Luther King Jr., and practiced powerful quotes before reciting them to crowds waiting along Badger Road. Walters, a longtime Madison resident, says the streets came alive as people followed the promenade making its way down Badger Road, up Park Street and over to Fisher Street before reaching Penn Park, where the parade blossomed into a full-fledged jubilee.
“It was such a beautiful thing,” says Walters, recalling years past. “It was just a lot of camaraderie … It was Black brilliance.”
Madison’s Juneteenth celebration has been ongoing since 1990 — 19 years before it became an officially recognized Wisconsin holiday in 2009, and 31 years before it became a federal holiday in 2021. Annie Weatherby-Flowers and Mona Adams Winston planned Madison’s first Juneteenth festivities with a committee of just 10 people, on a budget of $1,500. With limited resources, the first few festivals required a lot of creativity to develop a program reflective of Black Madison. The powerful experiences they were able to foster — encapsulated in Walters’ fond memories of the parade — are a true testament to the grit of Weatherby-Flowers, Adams Winston and their early collaborators, and their pride in Madison’s Black community.
Annie Weatherby-Flowers (on left) and Mona Adams Winston (on right) planned Madison’s first Juneteenth festivities with a committee of 10 people and a budget of $1,500.
“We really want our community to become more empowered through its rich heritage and history,” says Weatherby-Flowers. “On Juneteenth, we’re all the same. We all have a shared history, a shared culture and a shared goal.”
This year’s Juneteenth marks a special milestone. It’s 160 years since the fateful day when Union Army troops alerted the last enslaved people in Galveston, Texas, of their emancipation on June 19, 1865 — two years after Abraham Lincoln signed the Emancipation Proclamation.
The 160th anniversary of Juneteenth is occurring in a difficult political climate, where discussions around race and history are increasingly politicized, challenged and, in some cases, erased. In Madison, where we straddle the reality of being named one of the best places to live in the U.S. and one of the worst places for Black Americans, Juneteenth symbolizes resistance and gives Black Madisonians a chance to declare they belong.
At the same time, the anniversary comes as Madison’s Black community starts a new chapter. 2025 welcomes two cultural and enterprise centers — The Center for Black Excellence and Culture (currently under construction) and the Black Business Hub (opened in August 2024) — dedicated to uplifting Black voices and strengthening opportunities for Madison’s Black community.
Meanwhile, honoring 160 years of freedom at Madison’s 36th Juneteenth festival — the theme this year is “We Will Still Collectively Rise” — is an opportunity for Madison to celebrate the history of Black people in Wisconsin while recognizing that the journey toward inclusivity and equality is ongoing. This June, Black Madison will come together to acknowledge an enduring legacy of liberation that’s distinctly tied to some of Madison’s first Black settlers — a legacy that’s worth celebrating in the streets with music, singing and food, and that highlights the irreplaceable joy of being connected to and proud of one’s community.
Madison’s Festival
The first few years of planning Madison’s Juneteenth celebration were hard, admits Adams Winston. She remembers when Weatherby-Flowers first shared her vision for the event.
Originally from Milwaukee’s northside and working at the Madison Inner City Council on Substance Abuse at the time, Weatherby-Flowers says the idea for Madison’s Juneteenth festival was born from her own vivid memories of attending Milwaukee’s Juneteenth celebration, which is the oldest of its kind in Wisconsin and one of the oldest nationwide.
“It was the place where we saw everyone,” Weatherby-Flowers says. “The kids who came back from college, folks from across the town. It was like a homecoming — good food, good music, and it was fun and entertaining and educational.”
In 1989, Weatherby-Flowers moved from Milwaukee to Madison with her teenage sons for a fresh start. Shortly after that, she started assembling a small but mighty planning committee of around 10 people, including Adams Winston and Adams Winston’s then-husband, John Winston; Cheryl and Isadore Knox Jr.; and others.
Local sponsors chipped in $1,500 that first year. At times, Adams Winston and Weatherby-Flowers paid out of pocket for equipment and materials and relied on family and friends to ensure the event came together smoothly. Ultimately, Adams Winston says, the event became a family affair.
“We knew that we were [planning] such a wonderful day for the community — our beloved community,” Adams Winston says, “where we come together and just have a blast, between eating and singing and learning about our history.”
Knox says he remembers the first few festivals requiring a lot of creativity to develop a program reflective of Black Madison. He said the committee asked local educators to teach about Juneteenth and the African American soldiers who served in the Civil War, also known as Buffalo Soldiers. They invited local dance troupes to perform and vocalists to sing “Lift Every Voice and Sing,” a James Weldon Johnson hymn that’s often called the Black National Anthem.
“[Juneteenth] just drew a lot of creativity out of everybody,” says Knox. “The more someone got involved, the more they all had something cultural to add. It just worked.”
Christmas in June
Over the years, the Juneteenth celebration continued to grow, and at its peak in the early 2000s it welcomed nearly 15,000 people to Penn Park, according to Weatherby-Flowers. In those early years, the programming was overseen by the Madison Inner City Council on Substance Abuse, and later the Nehemiah Center for Urban Leadership Development, before Weatherby-Flowers launched the Kujichagulia-Madison Center for Self-Determination in 2006, which now hosts Juneteenth as its flagship program at Penn Park.
Each June, Penn Park is transformed by colorful tents spread across the lawn, brimming with history, performances and cultural exchange. The gospel tent, led by the African American Council of Churches, invites folks to enjoy musical stylings from local choirs. The heritage tent connects attendees to the African diaspora through food samples, textile showcases and community speakers. The kids’ tent and the “old school” tents cater to those specific generations — kids enjoy face paint and educational resources while elders swap stories and play cards.
Juneteenth celebration gallery
“To see Penn Park being used for dancing and music and tents and food and celebration felt like Christmas in June,” says Dr. Alexander Gee, pastor at Fountain of Life Covenant Church and founder of Nehemiah. “It was done with such excellence and passion that it made me so proud to be Black and [to] be Black in this community.”
Weatherby-Flowers says these traditions encourage Madison’s Black residents to engage with others in the Madison community while reflecting on their personal histories as Black Americans. She acknowledges that the number of attendees has decreased in recent years, now annually averaging about 2,500 to 5,000 people. Weatherby-Flowers says Madison’s Black community has changed over time, seeing shifts in population, economic conditions and social dynamics. Overall, she doesn’t view this decline negatively, but as a natural evolution of the community and how people engage with cultural celebrations. One of the greatest results of her commitment to the tradition is that it has inspired a new generation of organizers and leaders seeking to embrace the city’s local Black culture.
Julian Walters, who remembers plunging community leaders in dunk tanks and playing basketball at the Juneteenth event, now hosts his own annual block party at Penn Park every August to promote Black excellence in the community. He says “Ju Ju’s Annual Block Party,” which boasts a basketball tournament, scholarships, food and more, is directly related to his experiences during Madison’s Juneteenth festival at Penn Park.
Ju Ju’s Annual Block Party
“In a city like Madison, you can never have enough celebration,” he says. “It’s important to have block parties and Juneteenth and other celebrations because you want to feel like you belong in the city that you’re from.”
A Tale of Two Towns
In between celebrations, Walters points out that Madison still feels like “a tale of two different towns … and there aren’t a lot of opportunities here to learn about our culture and history.” The separation of Madison’s Black community has been a long-standing challenge. In the 1930s, Madison’s African Americans were geographically isolated by discriminatory redlining practices, which forced them to live in specific neighborhoods on the south and east sides and excluded many Black people from economic mobility. Landmark studies like the 2023 Race to Equity Report (first introduced in 2013) have also found that Madison’s Black residents are four times less likely than white residents to own homes regardless of their income level, and they experience poverty at a disproportionate rate in comparison to their white counterparts.
Weatherby-Flowers says celebrations like Juneteenth help to disrupt systems or silos that attempt to keep the Black community disenfranchised. The events also encourage them to embrace the spirit of Kujichagulia, a Kwanzaa principle representing self-determination (and the namesake of Weatherby-Flowers’ organization).
“When we first started [celebrating Juneteenth in Madison], there were pockets of Black people in Madison, and 35 years later, we are still fragmented, economically, socially, educationally, by the disparities,” Weatherby-Flowers says. “It’s better than it once was. However, it is not as good as it could be, because we have not been able to break down all of those barriers that hold us back collectively. So how do we do a better job of empowering our community, our total community, to become a more effective part of the city? That’s what this is about.”
While local celebrations seek to honor culture and teach Black history, the Trump administration has sought to rapidly roll back cultural observations like Juneteenth and other federal heritage holidays. Madison Mayor Satya Rhodes-Conway says the city of Madison will continue to support diverse programming despite federal attacks.
“We’re going to keep staying true to our values … There’s no way we’ll stop celebrating Juneteenth, and there’s no way that we’ll stop valuing the diversity that we find in our community, in our history and our future,” she says, adding that the city raises the Juneteenth flag every year in observance of the holiday. Gov. Tony Evers signed the first executive order raising the Juneteenth flag at the state Capitol in 2020.
“We have some very significant African American history going back for a very long time. … It’s really important for us to acknowledge all aspects of our history, and Juneteenth is very much a part of that,” says Rhodes-Conway.
Madison Mayor Satya Rhodes-Conway (left) says the city will continue to support diverse programming despite federal attacks.
As Madison’s 2025 Juneteenth theme “We Will Still Collectively Rise” suggests, Weatherby-Flowers is confident that Madison’s Black community and its celebrations will “survive and thrive” despite renewed threats to diversity. “We’ve been here before … this is not different. [We must] remember our history, remember our resilience, our ability to bounce back,” she says. “We have resources in our own community that have kept Juneteenth alive. We can still do that.”
‘We Will Still Collectively Rise’
As the city reflects on 160 years of Juneteenth and 36 years of its own observation of the holiday, local organizers continue to rally around the anniversary of the emancipation of Black Americans while forging a path toward a more just and inclusive Madison. Efforts include support for new intentional spaces where Black people can learn and experience fellowship, enjoy local events, unwind, create and take up space, and where organizations can build strong ties with young professionals — giving them an outlet to be fully themselves.
The Center for Black Excellence and Culture, currently under construction on Badger Road, will “proliferate Black culture, tell the stories of Black greatness and bequeath excellence to the next generation,” says Gee, the center’s founder. It will be a space to support Black business owners, provide sanctuary for mental and emotional wellness and serve as a gathering spot for Black people to laugh, talk, connect and build with one another, he says.
“Our hope is that we can make Black people proud to be Black and a Wisconsinite,” Gee says. “We want a space where we can find ourselves in our culture, just like the majority culture can find the reinforcements of its culture.”
Meanwhile, the Black Business Hub, which sits north of The Center for Black Excellence and Culture, is also changing the landscape of south Madison by offering another physical space for the city’s Black entrepreneurs. Led by the Urban League of Greater Madison, the Black Business Hub had its grand opening in August 2024 and now offers accelerator programs to train entrepreneurs as well as options for events, nonprofits and small businesses in need of office and commercial space.
Beyond these physical spaces, young leaders in Madison are also carving out programs and opportunities that celebrate their cultural pride, with a goal to make Madison a place young Black people can be proud of.
Kayla Conklin is a Madisonian who embodies the fervent spirit of Juneteenth. Conklin has lived in Madison for seven years and is president of the Urban League of Greater Madison’s Young Professionals, which has 75 members. Since becoming president, Conklin has worked with her team to develop a scholarship fund for Madison-area students, host networking events to help young professionals grow, and present an annual awards gala and Juneteenth party to celebrate Black culture. She says the group also prides itself on supporting any and all Black-led spaces and organizations throughout the city to promote unity and collaboration. Although she recognizes that the city still has work to do, she says the beauty of Madison is that it is committed and small enough to evolve into a thriving place for Black people.
“My favorite part of living in Madison, and why I truly believe that we have a lot of power to change here, is because it is a small city, and we do have a lot of resources,” Conklin says. “We’re really creating a legacy, creating opportunities for young people in our city and continuing to make that impact here.”
There is a fervent energy in Madison to create spaces and hold events that help Black residents feel a deeper sense of belonging. This transformation comes as the country stands at a crossroads — one that calls for a reimagining of how we protect these spaces and the communities we love. Most importantly, Weatherby-Flowers says, the city’s Black community must continue to “come together and collectively support each other.”
Whether you’re a long-time community member or a first-time attendee, consider this an invitation to Madison’s 2025 Juneteenth celebration at Penn Park on June 21. It’s more than an event — it’s an opportunity to amplify Black triumph, connect with local resources and build bridges in the community.
“We’re more than what the newspapers say. We’re more than what the statistics say,” Weatherby-Flowers says. “We are the hopes and the dreams of the slaves, and so let us not forget that as we continue to strive for inclusion and equity.”
The Making of a Holiday
A combination of “June” and “nineteenth,” Juneteenth, also known as Freedom Day or Emancipation Day, highlights that abolishing slavery was a gradual process. The abolition of slavery was neither immediate nor fully realized when Abraham Lincoln issued the Emancipation Proclamation in 1863. To remedy this, U.S. Maj. Gen. Gordon Granger issued General Order No. 3 to free more than 250,000 enslaved Black Americans in Galveston, two months after the end of the Civil War in 1865. This came two years after the Emancipation Proclamation and about six months before the ratification of the 13th Amendment, which abolished slavery for Black people who were still enslaved. Around 2,000 federal troops arrived in Galveston to announce the general order, many of whom were recently liberated Black men from the United States Colored Troops.
“The colored troops being in Galveston was actually an accident,” says Dr. Charles Taylor, author of “Juneteenth: A Celebration of Freedom” (published in 2002) and a retired Edgewood College professor. “They were sent from Virginia to guard the Mexican border. … They were low on supplies with a terrible storm, and the storm took them to Galveston, which was the first place they could get off their boats.”
Imagine the newly freed people of Galveston learning of their freedom from Black men arriving with the authority of the U.S. government now on their side. Taylor, who depicts the first Juneteenth in his latest book published in 2025, “Juneteenth: The Promise of Freedom,” says there was “tremendous emotional release.”
“People reacted in all kinds of ways,” Taylor says. “There were tears of joy. There was disbelief. There was a woman holding her baby who just kept saying, ‘Baby, you free. Baby, you free.’ There was an old man who hadn’t straightened his back out for years because of the cotton field and could [now] straighten his back out and lift his hands upward to the sky.”
Although the exact names of the Black troops who landed in Galveston in June 1865 are unclear, according to the Wisconsin Veterans Museum, two future Black Wisconsin residents were likely among the troops present when the order was issued to free the enslaved. Those two soldiers were Howard Brooks, who eventually landed in Madison, and Horace Artis, who later lived in Appleton.
Taylor says Madison’s connection to this pivotal day is no surprise, adding that “Madison has a long history of activism,” including strong ties to Juneteenth activism, which was largely led by the late Dr. Ronald “Doc” Myers, who spearheaded the national movement to make Juneteenth a federal holiday.
Raised in Milwaukee and a graduate of the University of Wisconsin–Madison School of Medicine, Myers went from state to state promoting the adoption of Juneteenth as an official state and federal observance. Myers traveled the country for over 20 years meeting with state officials advocating for Juneteenth, and according to Taylor, every time a state governor made Juneteenth an official holiday or observance, Myers would present them with the book “Juneteenth: A Celebration of Freedom.” Myers was even present in Milwaukee when former Wisconsin Gov. Jim Doyle signed a bill making Juneteenth Day a state holiday in 2009. Unfortunately, Myers died in 2018, three years before Juneteenth was declared a federal holiday.
“I just wish that Myers had lived to see what he had really started,” says Mona Adams Winston, who lived in Madison for many years and lobbied alongside Myers in Washington, D.C., in the early 2000s as a member of the National Juneteenth Observance Foundation board. In a 2021 tribute to Myers, Illinois Rep. Danny Davis said Myers was “one of the real reasons that President [Joe] Biden was able to sign into law Juneteenth as a national holiday [in 2021].” According to Davis’ address, Myers was instrumental in passing Juneteenth as an official observance in 45 states and the District of Columbia before it became a federal holiday.
Kynala Phillips is a contributing writer to Madison Magazine.
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