Annie Weatherby-Flowers Enters Her 36th Year of Leading Madison’s Juneteenth Celebration: A Juneteenth Day Community Icon

Annie Weatrherby-Flowers

Annie Weatherby-Flowers has been a chair or co-chair of the Madison Juneteenth Day Committee since the first celebration was held in Penn Park in 1989.

By Jonathan Gramling

For the past 35 years, Annie Weatherby-Flowers has headed up, once in concert with Mona Adams Winston and for the past 12 years solo, the Madison Juneteenth Day Committee and has been a community icon of Madison’s Juneteenth celebration held annually in Penn Park.

Annie has hinted loudly that this may be her last year in the leadership role. We wanted to make sure that Annie received her flowers while she was still the leader. The following comments are from people involved in Juneteenth, past and present:

Mona Adams Winston - When Annie and I met it was as if we had known each other forever. She had the dream and true inspiration for Juneteenth. She was able to form a committee that believed in her dream of a Community Event that would pull our Beloved Village together.

I felt like I was more of the detail person and was able to add my organizational and fundraising skills to the Juneteenth Celebration Committee. This is the reason I still worked with Annie three years after I moved to Mississippi. She has set Juneteenth up to be able to continue under another nonprofit. We are still very close and I wish her the very best as she moves on to the next chapter of her life.

Fabu Phillis Carter - I first met Annie as a new member at church.  She talked about the Juneteenth Celebration and I decided to take my young son and attend.

I could tell even then, this celebration was important to her.  Later I learned the history of how she and other African Americans celebrated in Milwaukee and so she brought the Juneteenth Celebration to the location where she and her family decided to make their new home.  Juneteenth has grown over the years, but at its heart and core, it has been Annie's vision and dedication that has made it unique and successful.  No one else in Madison has the detailed knowledge,care for our spirits, culture, history and family friendly focus as she does.   Annie has established relationships with city officials , written grants, and raised money, all while keeping her love of Black folks at the forefront to shape this celebration.

All of Madison should honor her 35 years of presenting Madison Juneteenth as a dedicated leader.  Juneteenth, a celebration of freedom, is such an important part of who we are and its importance must be remembered to all Madisonians and Annie's work continued.

Jacquelyn Hunt - Annie has been an amazing mentor, sister and friend to me!  She was my sponsor in my early recovery days.  She introduced me to My church home here in Madison.  Because of her I believed I could!  Annie and Mona gave both myself and Tequila our initial experience with Juneteenth.

I am actually the founder of the Juneteenth Parade, and it was Tequila and I who created the children, youth, and teen areas!  Yes Annie and Mona saw in us what we hadn't unleashed for ourselves.  Annie would lay out the theme each year and we made sure to bring it out in all the areas.

Later Annie entrusted me to create the Old Skool Area!  It has been an amazing 28 years serving alongside Annie as her desire is to ensure the Juneteenth Celebration remains intact and that our community is able to experience with pride the rich heritage of Black Americans!

Terri Strong - We honor and celebrate a true pillar of the Madison community—someone whose unwavering dedication to justice, equity, and the well-being of Black people has been nothing short of extraordinary.

Annie Weatherby Flowers  through decades of tireless work, had raised critical issues, uplifted voices too often unheard, and championed health equity with wisdom, courage, and grace. Whether advocating for civil rights, advancing affirmative action, or educating our community about the struggles and triumphs of African-American people, her impact has been powerful and far-reaching.

Her steadfast dedication to Juneteenth—as both a celebration and an educational platform—has been nothing short of formidable. She has prioritized this sacred tradition year after year, for 35 years ensuring that the significance of freedom, resilience, and Black history remains centered in our collective consciousness. Madison’s Juneteenth celebration bears the unmistakable mark of her heart, vision, and commitment.

Ms. Annie, has led with strength and purpose, even in the face of personal health challenges, never once letting them slow her mission. Her resilience inspires us all, and her legacy is deeply woven into the fabric of this city.

We thank Annie for her fierce advocacy, her steady leadership, and her heart for the people. Madison is better because of Annie Weatherby-Flowers

Janine Stephens-Hale - I would be delighted to share some thoughts on the extraordinary contributions of Ms. Annie Weatherby Flowers to Madison's annual Juneteenth celebration over the past 35 years. Her leadership and coordination have been truly remarkable, making the event a cornerstone of our community.
Personally, Ms. Annie has been an incredible mentor to me over the last decade. I have learned a tremendous amount from her wisdom, dedication, and passion for Juneteenth and Black history. Our partnership has been invaluable, and I eagerly anticipate its continuation, particularly as we explore the future leadership of the annual Juneteenth celebration with the Center for Excellence in Black Culture.
Ms. Annie has done an exceptional job in moving the needle and fostering greater awareness within our community. As she considers retirement this year, she will undoubtedly leave behind some very significant shoes to fill. I am deeply grateful for her interest in me as a potential successor to lead this important tradition forward.

Christine Russell - From the pews of Fountain of Life Church, to the boardrooms discussing health advocacy, to the tents of community celebrations, Ms. Annie has been a steady and subtly powerful presence in my life since I was a young girl. I have had the honor of working directly, and indirectly with Ms. Annie through the Lupus Support Group for Women of Color in partnership with the Foundation for Black Women's Wellness, where her passion for creating safe spaces for Black women to heal, learn, share and grow is unmatched.

Our partnership expanded as we sit together on the Community Advisory Board (CAB) of the All of Us Research Program, where she champions the importance of equitable health research and representation. Ms. Annie is relentless in her mission to ensure Black and Brown communities understand the power of knowing their health history, their family stories and how that knowledge is inextricably tied to our strength and resilience as a community.

And of course, there is Juneteenth! Every year, Ms. Annie has shown up - organizing, speaking, guiding and directing to ensure that this Madison community understands not only the history of our freedom - but the responsibility of keeping our history alive. She is a living bridge - between generations - between the past and the future - between pain and healing. Her legacy is not just in the work she's done, but in the lives she has touched --- including mine.
Thank you, Ms. Annie. For everything you do, and everything you are. We love you!

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Sonia Spencer - Annie’s leadership isn’t just about organizing the Juneteenth event; it embodies Kujichagulia’s mission of personal and economic empowerment and addresses social disparities in the Madison area. Through her steady hand and unwavering commitment, the Juneteenth weekend has consistently been more than a celebration; it’s a powerful statement of community, heritage, purpose, and progress.

Serving on the committee these past two years has been an honor. I’m deeply grateful to have contributed alongside such passionate leaders and visionaries. Annie, thank you for your steadfast leadership, your heart for the community, and the legacy you continue to shape through your work.

Corinda Rainey-Moore - Annie as you know is one of the co-founders of Juneteenth. I have been working with Annie on Juneteenth for about the past  20 years. Annie has poured a lot into Juneteenth making this an event that everyone regardless of ethnic background can enjoy.  What I like most is her ability to collaborate to make sure that all voices are brought to the table around this event. She brings together people of all ages and backgrounds to this event. Annie does not often get the credit she deserves for  being a founder and for keeping this event going for as long as she has. Juneteenth is not just a celebration, it is about history, culture, and the resilience of African- Americans. Annie  wants us to always remember who we are as  Black people because by knowing and understanding the rich history that is ours, we can believe and know that there is nothing that can stop us as a people. She not only believes this, but she lives this every day. When it comes to Juneteenth, she is  Visionnaire extraordinaire.

Roxanne Johnson - I have known Annie for over 25 yrs. She has played a pivotal role in my life. I was a member of The Women of the Unashamed that was led by her. We traced together, supported each others families, held one another accountable and did everything in love. She stood on how God loves his people and taught each broken woman how to trust the God in each of us.

Annie also saw so much more in me than I knew about me. I had my first acting gigs under her guidance as she produced plays and small skits for Juneteenth. Annie always had a way of never making you feel less than. You knew what she said and did always came from a place of love. May God continue to bless Mrs Annie with good health, healing, peace and love.