This Week in Key West: October 19 - October 25, 2026

Looking for things to do in Key West this week? Discover live music, local events, art walks, happy hours, nightlife, and island happenings taking place October 19 – October 25 , 2026.

⭐This Week’s Featured Event

🎉 MASQUERADE MARCH & OURKEYWEST WATCH PARTY & LUAU

Friday, October 23 — 5:30 PM
One of the local’s favorite Fantasy Fest events! The Maquerade March, also known as The Locals’ Parade, is a costumed street takeover celebrating creativity, community, and pure Key West spirit. The walks starts at Petronia & Francis and comes down Fleming, takes a left on Simonton St. and goes right by OurKeyWest. We will hosting a watch party luau from 5-8 pm. Come by and watch the parade with us- bring your grass skirt & coconut bra. Enjoy some Polynesian chicken & rum punch. FREE EVENT.

🌟 This Week’s Highlights

PARTY IN MY PANTS: A SEXY CABARET

Monday, October 19 @ Key West Theater | 512 Eaton Street —7:30 pm
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go to PartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.

16th ANNUAL TUTU TUESDAY – NERDELODEON

Tuesday, October 20th @ Genreal Horseplay | 423 Caroline Street |—6pm-2am
This year’s theme is NERDELODEON — part after-school special, part cartoon fever dream, part Revenge of the Nerds energy. Jocks, geeks, dweebs, teachers’ pets, hallway weirdos, cartoon kids, and full-grown tutu monsters all end up at the same party — all in tutus, of course. We’re taking over the Caroline Street district with 10+ DJs across 4 bars in Downtown Key West. General Horseplay is home base. Pick up your wristband there, then bounce around 4 bars packed with DJs, lights, lasers, tutus, silliness, other surprises, and nerdy little chaotic worlds. One wristband gets you into the whole goofy mess. As always, forever and ever: No Tutu. No Entry. TICKETS

The 5th ANNUAL PARTY LIKE A ROCKSTAR

Wednesday, October 21 @ Kaya Island Eats at the Key West EmPOURium | 618 Duval Street | 6 PM–Midnight
Get ready for one of Fantasy Fest’s most electrifying nights, featuring live music, incredible costumes and pure rock ’n’ roll energy! 8 PM: Guitar Shred-Off featuring outstanding local and out-of-town musicians competing for cash prizes! 9 PM: Jeff Clark’s All-Star Band takes the stage for a powerhouse live performance! 10 PM: Costume & Air Guitar Contest with cash prizes! Dress as your favorite rock star and bring your wildest stage presence. Come dressed to rock. Come ready to party. Don’t miss the 5th Annual Party Like a Rock Star!

PET MASQUERADE

Wednesday, October 21 @ Truman Waterfront Amphitheater | 6:30 PM
Join us for our famous Pet Masquerade Event. You will see a carousel of frisky pets and playful owners performing for fame, fortune and prizes beginning at 6:30PM on the stage of the Key West Amphitheater at the Truman Waterfront Park! Think you and your furry, feathered or slithery friend have the purrfect outfit? Four categories to enter including Junior, Pet/Owner Lookalike, Most Exotic, Best Theme Adaptation, as well as Overall Winner/Best in Show. $25 / entry; benefits the Monroe County Sheriff’s Office Animal Farm and produced by Florida Keys Media. Registration begins at 5 PM. Show starts at 6:30 PM. FREE to watch, plenty of FREE seats available or bring your blanket and lawn chair. Food and beverage available on site. 21 E. Quay Rd.

SLOPPY JOE’S 47th ANNUAL TOGA PARTY

Thursday, October 22 @ Sloppy Joe’s Bar| 9 PM
Sloppy Joe’s 47th Annual TOGA! Party “An ORIGINAL Fantasy Fest Event!” Get your TOGA! On and find out. why we are “Still The Best TOGA! Party in Town!” Wear a traditional ancient TOGA! or dare to create your own TOGA! using the Fantasy Fest theme “Musical Icons & Iconic Musicals”. Live music starting at 10am! Enter our costume contest & win big! 1st Place $500 Sloppy Joe’s Gift Card. Sign up begins at 8:15pm next to the stage with the contest starting at 9:00pm. You may enter the contest as an individual or group of 2-4 people (Must be in TOGA! to enter the contest). “Nightbreakers” takes the Sloppy’s Stage following the contest to keep you dancing all night long!

THE 5th ANNUAL CAPTAIN MORGAN’S PIRATE PARTY

Friday, October 23 @ The Backyard Bar | 618 Duval Street | 6:30PM-10:00PM
Join us at The Backyard Bar for a legendary night of rum, revelry, and high-seas mischief! This year’s pirate bash features nautical tunes and pirate shanties, a full-on costume contest, and a treasure chest of cash prizes: $500 for first place, $300 for second, and $200 for third. Whether you come as a fearless captain, a rogue buccaneer, or a siren of the seas, it’s your chance to sail into glory — and maybe leave with some loot in your pocket. NO COVER – Bar open till 1AM

DEEP EDDY VODKA FANTASY FEST PARADE

Saturday, October 24 @ The Backyard Bar | 618 Duval Street | 7 PM
Join 70,000 exuberant partygoers as this year’s Key West Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes and dazzling dancing groups! It doesn’t get any wilder than this! Parade steps off at 7 PM FREE. Live Web Cams

CHILDREN’S DAY

Sunday, October 25 @ Bayview Park | 12-5 PM
A family event featuring food, rides, games, arts and crafts and a costume contest for children! Located at Bayview Park.

Planning a future trip to Key West?

Browse festivals, concerts, races, holiday celebrations, and special events happening throughout the year.

View our complete 2026 Key West Events Calendar →

🎵 Live Music & Entertainment

🎉Fantasy Fest Partys

Monday, October 19

• Nick Norman @ Rams Head Southernmost— 11AM–2 PM
• Mary Spear @ The Gardens Hotel— 5–7 PM
• Martinis w/ Melodic Beats @ General Horseplay— 9 PM

Tuesday, October 20

• Ross Brown @ Rams Head Southernmost— 11AM–2 PM
• John Dion @ The Gardens Hotel— 5–7 PM
• Glow Hours @ Hugh’s View atop Studios of Key West— 6–8 PM
• Radio Hero @ Sloppy Joe’s— 10 PM

Wednesday, October 21

• Sharese @ Rams Head Southernmost— 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel— 5–7 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Nightbreakers @ Sloppy Joe’s— 10 PM

Thursday, October 22

• Robert Douglas @ Rams Head Southernmost— 11 AM–2 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Electric Blue Yonder @ Green Parrot Bar— 5–7 PM
• Mac Calhoun & Colton Gleghorn @ Key West Empourium— 6 PM
• The Lucky Ones @ General Horseplay— 9 PM
• Nightbreakers @ Sloppy Joe’s— 10 PM

Friday, October 23

• Andy Westcott @ Rams Head Southernmost— 11 AM–2 PM
• Happy Hour All Day @ The Roost— 12–6 PM
• Shastina @ General Horseplay— 7 PM
• Nightbreakers @ Sloppy Joe’s— 10 PM

Saturday, October 24

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Polynesian Party w/ Casey Turner @ Key West Empourium— 3 PM
• Zach Lovering @ General Horseplay— 7 PM
• The Blues Party @ Key West Empourium— 8–1 AM
• Nightbreakers @ Sloppy Joe’s— 10 PM

Sunday, October 25

• Marjorie Lee @ Rams Head Southernmost— 11 AM–2 PM
• Sam Carlson @ Green Parrot Bar— 1 & 3 PM
• Scott Marischen @ The Gardens Hotel— 5–7:30 PM
• Karaoke Night @ General Horseplay— 8 PM
• Nightbreakers @ Sloppy Joe’s— 10 PM