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.

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.

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. Whether you’re an avid art collector or simply looking for a fun afternoon exploring Key West’s creative scene, this tour offers an engaging and memorable Womenfest experience.

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. Since then, she has taken her infectious live energy to stages across the East Coast and Midwest, sharing bills with artists including Morgan Wade, Riley Green, Parmalee, Lauren Alaina, Lonestar, Edwin McCain, David Nail, Ashland Craft, and more.

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!

The Dude abides. And tonight, he abides at Mary Ellen’s.

The Big Lebowski gets better every time you see it, and even better with a cold drink and a room full of people who already know every line. White Russians will be served.

One movie. One legendary album. Decades of people saying, “Okay, but hear me out…”

Experience one of the most talked-about film and music pairings of all time!

For decades, audiences have claimed that The Wizard of Oz and Pink Floyd’s iconic album, The Dark Side of the Moon, sync together in surprising and often uncanny ways. Coincidence? Happy accident? Pure imagination? The debate continues—and now you can experience it for yourself.

Official Lobsterfest Event!

Lobster roll eating contest… $30 to enter. Comes with 1 lobster roll – the fastest to finish it completely, wins!

Get ready to test your knowledge at the Key West Lobsterfest, featuring an evening of Pub Style Trivia with a Lobster Twist. For $50 per person, attendees can enjoy the competitive atmosphere along with a fresh lobster roll and a drink included with their entry. Not Hungry? For $25 per person, attendees can enjoy the competitive atmosphere along with a drink only included with their entry.

Get ready for a little friendly competition! Join us on Sunday, July 26th from 4:00 PM – 9:00 PM as our talented bartenders go head-to-head in the ultimate summer showdown: The Horseplay Punch Classic.

They’re mixing up their best large-format concoctions, and you get to be the judge.

Possibly the greatest concert film ever made.

David Byrne dances. The band gets bigger. The suit gets larger. The music gets louder. Somehow it all makes perfect sense.

Doors at 7. Film at 8ish. 

Tuesday, July 14 • Tasting 6:30 PM • Film 8 PM

Join sommelier Daniel McCurdy for a special wine tasting before the film exploring the wines of the central coast. No merlot will be served. Lite bites from Chef Martha.

A movie that launched a thousand wine clubs and nearly destroyed the reputation of merlot forever. Funny, moving, and proof that middle-aged existential crises can occasionally be entertaining.

Join us on the Old Town Trolley Tour for the "Paint the Town Proud Pub Roll", an exciting adventure outside Key West's historic and vibrant Gayborhood. This unique event celebrates the island's LGBTQ+ cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Be sure to dress in your favorite color of the rainbow to win best dressed! We'll kick off the tour at Bobby's Monkey Bar, where you can enjoy delicious breakfast bites and a welcome drink. A cash bar is also available for mimosas, Bloody Marys, or any other drinks you might want to have before the tour begins!

Join us at Tropicado Mojito Bar at La Concha Hotel for an immersive, hands-on mojito experience in the heart of Key West!

Shake, “slap”, and sip your way through the art of crafting the perfect mojito as you explore Papa’s rum, fresh ingredients, and the vibrant spirit of Havana. This interactive class is a must-do for cocktail enthusiasts, curious beginners, and anyone looking to elevate their island experience.

Presented by the Key West Business Guild and Gay Key West, this year's Pride event carries the overarching theme of “Color the island: A Celebration of Identity Through Color & Creativity.” Join us for a vibrant kick-off to Pride 2026 as we transform the island into a living canvas of self-expression, artistry, and community. Color the Island is more than an event; it’s an immersive celebration of identity, where every hue tells a story, and every voice adds to the theme. The celebration features local DJ Mr. Enjoy, local vendors, delicious food, and unlimited drinks! All included with your entry! Come ready to color the island with pride!

Join us to celebrate the end of Songwriters Festival with a Southern-style brunch at Williams Hall's Unity Table before the "Sunday Songs: Music & Mimosas"

Brunch includes exclusive balcony seating for the show.

It's Songwriter's Festival in Key West, and songwriters are famously funny... So join us for a night of musical comedy!

Keifer Thompson is an award-winning country music artist and songwriter and now comedian. He is co-founder of the Grammy nominated multi-platinum country music duo Thompson Square. Keifer will be joined by hit songwriter Bobby Pinson and singer/songwriter Paul Orehovec. He will also be joined by a few surprise comedians and musical guests, (local and visiting), performing brilliantly fun original and parody songs that you've never heard.

Kick Off Songwriters Week on the Water with Erica "Sunshine" Lee! ☀️🎤

Get ready for the ultimate private concert experience! We’re hitting the waves for 6 hours of sun, music, and good vibes. Catch a live 1-hour performance by Erica "Sunshine" Lee while we cruise.