Key West Arts & Culture Events

Browse Hey Key West's current arts & culture event grouping, with dates, venues, and details.

Party in My Pants: A Sexy Ass Cabaret (10/19) — October 19, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Party in My Pants: A Sexy Ass Cabaret (10/20) — October 20, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Party in My Pants: A Sexy Ass Cabaret (10/21) — October 21, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Party in My Pants: A Sexy Ass Cabaret (10/22) — October 22, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Party in My Pants: A Sexy Ass Cabaret (10/23) — October 23, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Sam Carlson Sound at 1:00 and 3:00 — October 25, 2026 · 1:00 PM – 4:30 PM · Green Parrot Bar: Two sets: 1:00-2:30 and 3:00-4:30. Sam Carlson leads his Bluegrass/Americana Quartet onto the The Parrot stage (Browse group: Arts & Culture)
Bingo for Key West Art & Historical Society — October 26, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Garrison Keillor and Erica Rhodes: “The Crazy Uncle and His Sensible Niece" — October 27, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Zombie Bike Ride — October 29, 2026 · Duval Street: A fun and spooky bike ride through Key West where participants dress in zombie costumes. (Browse group: Arts & Culture)
Will Kimbrough — October 30, 2026 · 5:00 PM (Doors 4:00 PM) · Key West Theater (Browse group: Arts & Culture)
Buffett Through the Years — October 30, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Jim Morris Tribute — October 31, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
52nd Annual Halloween Costume Contest — October 31, 2026 · 9:00 PM – 11:59 PM · Green Parrot Bar: Rested and Ready, or Ready or Not, on Halloween Night, FUNK YOU brings electrifying funk rock onto The Parrot stage for The Green Parrot Bar’s 52nd Annual Halloween Party and Costume Contest, on Friday, October 31st, with shows at 5:30, 9:00 and 11:00 p.m with costume judging starting around 9:00. It’s been called The Party We All Train For and Locals’ Night to Howl. “To the best of our knowledge, this is indeed the 52nd Annual Green Parrot Halloween party, says, manager Jim Fossum, we’re fairly sure of that. What we are very sure of is that it’s still “The Locals Night to Howl” and Ajeva is going to blow the roof off this place. (Browse group: Arts & Culture)
Sunset Celebration — November 1, 2026 · 5:30pm · Mallory Square: A nightly celebration at Mallory Square featuring local artisans, street performers, and beautiful sunsets. (Browse group: Arts & Culture)
Bingo for Studios of Key West — November 2, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Key West Art Walk — November 5, 2026 · 6:00pm - 9:00pm · Various Galleries: An evening of art and culture as galleries on Duval Street open their doors for a night of art viewing and socializing. (Browse group: Arts & Culture)
The Ocean Blue — November 7, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bruce Cockburn & Livingston Taylor — November 8, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bingo for Sister Season Fund — November 9, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
A Tribute to the Songs of Pete & Wayne, with Pete Jarvis, Larry Strickland, Ray Fogg & Friends — November 14, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
The Garcia Project with Special Guests Jess & Jill (Acoustic Opening Set) — November 15, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bathtub Gin Quartet at 1:00 & 3:00 — November 15, 2026 · 1:00 PM – 4:30 PM · Green Parrot Bar: Two 90-minute sets: 1:00-2:30 and 3:00-4:30. Photo Credit: Bill Klipp (Browse group: Arts & Culture)
Bingo for Key West Art & Historical Society — November 16, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Marty Stuart and His Fabulous Superlatives — November 19, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Dusty Slay: The Neighborhood Guy Tour — November 20, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Dusty Slay:The Neighborhood Guy Tour — November 21, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Kristen McNamara: Stories & Songs - Live Recording at the Key West Theater — November 21, 2026 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Arts & Culture)
The Buena Vista Orchestra — November 22, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bingo for Key West Wildlife Center — November 23, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Peter Mayer: A Stars & Promises Christmas "This Town" — November 29, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Sunset Celebration — November 30, 2026 · 5:30pm · Mallory Square: A nightly celebration at Mallory Square featuring local artisans, street performers, and beautiful sunsets. (Browse group: Arts & Culture)
Bingo for Irreverent Warriors — November 30, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Sunset Celebration at Mallory Square — December 1, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
Key West Art Walk — December 1, 2026 · 6:00pm - 9:00pm: An evening of art and culture as local galleries open their doors for an art walk showcasing local artists and their works. (Browse group: Arts & Culture)
Happy Christmas Baby - Featuring the World’s Greatest Christmas Songs from ABBA to Bing Crosby (8PM) — December 2, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Happy Christmas Baby - Featuring the World’s Greatest Christmas Songs from ABBA to Bing Crosby (4PM) — December 2, 2026 · 4:00 PM (Doors 3:00 PM) · Key West Theater (Browse group: Arts & Culture)
Sunset Celebration at Mallory Square — December 3, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
Sunset Celebration at Mallory Square — December 5, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
Bingo for Studios of Key West — December 7, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays — December 10, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)