Key West Arts & Culture Events

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

Summer Bingo Night (Free Entry) — September 2, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
Key West Art Walk — September 3, 2026 · 6:00pm - 9:00pm · Various galleries on Duval: Explore the vibrant art scene of Key West during the monthly Art Walk, featuring galleries and artists showcasing their work. (Browse group: Arts & Culture)
Sunset Celebration — September 3, 2026 · 6:28pm · Mallory Square: Experience the nightly Sunset Celebration at Mallory Square, featuring local artists and performers as the sun sets over the Gulf. (Browse group: Arts & Culture)
Occupational Hazard, The First Coral Reefers - SOLD OUT — September 5, 2026 · 2:00 PM (Doors 1:00 PM) · Key West Theater (Browse group: Arts & Culture)
Cayman And The Mango Men: A Buffett Tribute Soundcheck Set — September 6, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00 Join us for a special Soundcheck set to celebrate Jimmy Buffet lead by our friend (and Jimmy's) Cayman Smith-Martin. When life gives you limes, make margaritas. (Browse group: Arts & Culture)
Womenfest — September 6, 2026: Womenfest is a celebration of women, featuring a variety of events including parties, workshops, and entertainment throughout Key West. (Browse group: Arts & Culture)
Bingo for Studios of Key West — September 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)
Occupational Hazard, The First Coral Reefers: 2nd Show Added by Popular Demand! — September 7, 2026 · 2:00 PM (Doors 1:00 PM) · Key West Theater (Browse group: Arts & Culture)
Summer Bingo Night (Free Entry) — September 9, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bingo for Sister Season Fund — September 14, 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)
Summer Bingo Night (Free Entry) — September 16, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
32nd Annual Tradesman Appreciation Day — September 18, 2026 · 4:00 PM – 7:00 PM · Green Parrot Bar: Now an annual celebration of ours in September, Tradesman Appreciation Day was conceived as a one-off in 1994, when great American sculptor John Martini, whose studio was then located in a foundry on the old Navy base just down the street from The Parrot, would frequent our saloon for a drink after long, late-night sessions creating his unique metal sculptures. The medium Martini chose to work with, steel-plate and cast-iron, was a physically-challenging one, so he came to The Green Parrot often, to recruit the help of the able-bodied, but often elusive tradesmen known to frequent our corner. An offshoot of his search was his creation of an 8-foot iron sculpture, inspired by the tradesman he found here, a piece entitled, "Where's Jimbo and the Other Giants of the Building Trade?" acquired, quite fittingly, and hangs in The Bar today. Unveiled with great ceremony, the sculpture featured abstract figures, one wielding a plumber's wrench, plus as carpenter, an electrician, a female painter, as well as sheet-rocker, balanced on his drywall stilts, a facsimile of what the Parrot oft represented -- a bar that has been "Keeping the Working Men and Women of Key West Lubricated Since 1890". On that day, what seemed to begin as just another Parrot party became the first Tradesman's Appreciation Day. To mark the occasion, we annually issue laminated Tradesman and Tradeswoman Passes, complete with name, Polaroid photo, occupation and authorization. Even visiting President Jimmy Carter got one. And rambling Key West tradesmen and tradeswomen began using the card as their photo ID! (Browse group: Arts & Culture)
Bingo for Key West Art & Historical Society — September 21, 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)
Summer Bingo Night (Free Entry) — September 23, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
Bingo for PBIS — September 28, 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 — September 30, 2026 · 6:15pm · Mallory Square: Wrap up the month with the Sunset Celebration at Mallory Square, enjoying the local culture and beautiful views. (Browse group: Arts & Culture)
Gov't Mule & Ziggy Marley at Coffee Butler Amphitheater — September 30, 2026 · Doors: 5:30 PM / Show: 6:00 PM · Coffee Butler Amphitheater: Live show at the Coffee Butler Amphitheater (The Key West Amp), Truman Waterfront. (Browse group: Arts & Culture)
Key West Art Walk — October 1, 2026 · 6:00pm - 9:00pm · Various Galleries: An evening of art and culture featuring local galleries showcasing their latest exhibitions. (Browse group: Arts & Culture)
Party in My Pants: A Sexy Ass Cabaret (10/17) — October 17, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
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)
Zombie Bike Ride — October 22, 2026 · Duval Street: A fun and spooky bike ride where participants dress as zombies and ride through the streets of Key West. (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)
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)
Buffett Through the Years — October 30, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Will Kimbrough — October 30, 2026 · 5:00 PM (Doors 4:00 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)
Jim Morris Tribute — October 31, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
Sunset Celebration — November 1, 2026 · 1.5 hours before sunset · Mallory Square: A nightly celebration at Mallory Square featuring local artisans, performers, and beautiful sunset views. (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)
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 — 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)
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)
The Buena Vista Orchestra — November 22, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)