Popular Key West entertainer, Randy Roberts will emcee and arrange the show this year. WEOW’s Rudegirl oversees the music. Twelve to Fifteen contestants will hit the stage to show their Headdress creations, judged from the shoulders up, and vie for the first prize of $5,000. Performances by some of Key West’s best local talent from over the years will again be featured. There is bar service and specialty wine; food may be preordered and delivered to your table. Tickets are $320 for a premium table of 4, $270 for a VIP table of 4, with Chair seating at $35 and General Admission (grass seating) at $30.

Once upon a time… the heroines stopped behaving, the villains got seductive, and bedtime stories were rewritten under the glow of candlelight and cocktails. Join us for a decadent night of mystery, mischief, and magic, where fairy tales go rogue and the monsters under the bed are invited in for a drink. ✨ Dress as your inner Vixen or Villain—a wicked queen in velvet, a dreamy siren in silk, a seductive beast from the shadows. Whether you come draped in lace or crowned in horns, your fantasy is welcome here.

Join us for a fabulous Drag Brunch on Sunday, September 7, from 12–3 PM, with dazzling performances starting at 1 PM! Enjoy a vibrant afternoon of entertainment, laughter, and a delicious buffet featuring shrimp bisque, French toast with berries, eggs, bacon, sausage, home fries, cured salmon, benedicts, jerk chicken with yellow rice, croissants, fresh fruit, salad, and sweet treats like flan and key lime pie. Grab your friends, sip something bubbly, and get ready for a Sunday full of glam and good vibes!

DJ Rude Girl is back and will be providing the tunes all night long! Hosted by the glittery empress, Chantal P. Big Hair, Bold Looks, and All the Diva Energy You Can Handle! Get ready to step back into the most glam, outrageous, and fabulous decade of them all! Join us for Decades of Divas: 80’s Prom—a night where neon reigns, glitter rules, and everyone is the star of their power ballad.

Join us for a high-energy concert celebrating iconic women in music through many generations. Featuring powerhouse local vocalists and unforgettable hits, this show brings the evolution of women’s artistry to life. One decade, one diva at a time. 

Now Cooler Than Ever—Literally! We’re tossing things up this year—indoors and in the A/C! Join us for the 5th Annual Cornhole Competition at American Legion Post 168, where the bags will fly, the drinks will flow, and the vibes will be unbeatable.

Celebrate Pride with an unforgettable journey through Key West’s vibrant LGBTQ+ past and present! Hop aboard our Pride History Trolley Tour, we will take you through the most iconic queer landmarks and honor the trailblazers who paved the way. Limited seating is available! But the celebration does not stop there – our final stop is the ultimate Pride Pool Splash at the newly renovated,  La Concha Key West, Autograph Collection - 430 Duval St. Step off the trolley and into one of Key West's hottest pool spot for an afternoon of community, sun, and music by local Dj, Mr. Enjoy! Enjoy a full cash bar and an included BBQ buffet with an island twist made by Executive Chef, Juan Cuadra. Whether you are here to learn, dance, or simply soak it all in, this Pride experience is one you will not want to miss!