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  • Purple background with text announcing the 5th Annual Corn Hole Tournament and Fundraiser called 'Beat the Heat Indoor Cornhole Tournament.' The event is part of Key West Women Fest and encourages indoor gaming with colorful graphics and palm trees.

    Cornhole Tournament

    Thursday, Sept 3 ~ 12:00pm

    Get ready for a little friendly competition at the Annual Corn Hole Tournament & Indoor Games! Whether you’re a seasoned cornhole champion or just looking to have some fun, this event is the perfect opportunity to enjoy some spirited competition with fellow Womenfest attendees. In addition to the cornhole tournament, a variety of indoor games will keep the fun going for everyone. Grab a partner, make some new friends, and join us for an afternoon of games, camaraderie, and plenty of Womenfest fun!

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  • Maddie Rean in Concert

    Friday, Sept 4 ~ 8:00pm

    Raised in the rural heart of South Carolina, Maddie Rean brings a little bit of rock, a whole lot of country grit, and a voice you won’t soon forget. Rooted in classic and Southern rock, country, blues, and a touch of rap, Maddie has created a sound all her own—bold, soulful, rebellious, and unmistakably Southern. Maddie first caught national attention when her original song “Whiskey and Women” exploded on social media, earning more than 700,000 views and helping grow her following to more than 90,000 fans.

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  • Black and white illustration of a woman singing into a vintage microphone, with a piano below her. The woman has large earrings and her hair tied back. The text around the image reads "DIVAS THROUGH THE DECADES: A Celebration of the Music of Lady Ladies of Music History." The logo at the bottom left says "Key West WOMENFEST," and the production credit at the bottom right says "Produced by: Marjory Lee."

    Gallery Trolley Tour

    Saturday, Sept 5 ~ 11:00am

    Celebrate the creativity and impact of women in the arts on this inspiring trolley tour of Key West’s women-owned and women-managed galleries. In honor of this year’s Lost Women in the Arts theme, you’ll visit a curated selection of local galleries, meet the artists and gallery owners behind them, and discover the stories, talent, and vision that continue to shape Key West’s vibrant arts community. Each gallery stop includes a complimentary beverage, giving you the chance to sip, socialize, and enjoy each unique space while learning about the featured artists and their work.

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  • Colorful digital graphic with neon text that reads 'Key West Women Fest 80s Prom' against a space-themed background with geometric shapes and lightning bolts.

    80's Prom

    Saturday, Sept 5 ~ 7:00pm

    Dust off your shoulder pads, tease up your hair, and get ready to dance the night away at the Annual Womenfest ’80s Prom! This year’s celebration shines a spotlight on the Lost Women in Music, honoring the groundbreaking female artists whose voices, style, and influence helped define one of the most unforgettable decades in music. Come dressed in your favorite ’80s-inspired attire; whether you’re channeling an iconic music legend, rocking classic prom fashion, or creating your own totally rad look. Dance to the biggest hits of the decade, strike a pose for prom-worthy photos, and celebrate the women who made the ’80s soundtrack unforgettable. Costumes are NOT required, so grab your date, your friends, or come solo and make new ones as we relive the magic of prom, Womenfest style.

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  • Drag Brunch

    Sunday, Sept 6 ~ 12:00pm

    Wrap up an unforgettable Womenfest at our fabulous all-welcome Closing Drag Brunch, hosted by Hugh Janus! Enjoy spectacular drag performances, a special performance by our Queen Mother, Claire Brummell, delicious food, and nonstop laughter as some of Key West's most talented entertainers take the stage throughout the afternoon. Indulge in an abundant brunch buffet including flan and Key lime pie.

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