October 2026 Key West Events & Festivals

Plan your Key West trip with this calendar of October 2026 events, festivals, concerts, and things to do.

  • 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)
  • Key West Farmers Market — October 1, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring local produce, crafts, and artisanal goods. (Browse group: Food & Drink)
  • Good Trees River Band at 5:30 & 9:00 — October 1, 2026 · 5:30 PM – 11:00 PM · Green Parrot Bar: Two sets: 5:30-7:00 and 9:00-11:00 Good Trees River Band's June 2020 full-length album "Hold on to Your Horses" grabbed the attention of listeners throughout the Northeast and beyond. This release was the result of a hardworking history - spreading their musical magic through grassroots gusto. GTRB's sound has evolved immensely since the bands original formation. Initially drawing inspiration from Jam music and traditional Americana, the sound established in the early years was loose, but fun, maybe even slightly subdued. As the band developed further, so did their sound, reflecting a heavier and more psychedelic influence in their music. The band now is firing on all cylinders, and their live shows touch on all fronts of this ever-broadening soundscape. Formed in 2015, GTRB started as 3 high school friends in Massachusetts who wanted to take their musical collaborations to the next level. A thriving first year of open mics, bar gigs, and private parties with nobody in the bass seat was motivation to reshape the group and take things more seriously. 2016 saw the addition of Ned Brady on the bass, which sparked a four-track EP and a quick splash into markets beyond Southeast MA. Their first full-length tour in Summer 2019 spanned 20 dates throughout all of New England and into NYC, NJ, and Virginia. The fresh GTRB lineup is now five members strong & regularly performing and touring throughout the Eastern USA with shows from Maine to Macon to Key West. They stand out on festival lineups in their own right, while feeling fortunate to have shared bills with artists such as Ripe, Kung Fu, Eggy, and West End Blend, as well as Larry Keel, The Claypool Lennon Delirium, Adam Ezra Group, Strange Machines, and more. Keep your eyes and ears out for many musical moments and appearances to come! (Browse group: Festivals)
  • Sunset Celebration — October 1, 2026 · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Moonstone Riders at 5:30, 9:00 & 11:00 — October 2, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30. Come join Moonstone Riders on a rock’n ‘roll journey through a twangy world of psychedelic funk! The band features Matt Benfield on guitar and vocals, Marcia Winslow on vocals and percussion, and Jeffrey James on bass and vocals. The Riders, from Naples, FL, are known for their energetic live shows, which often feature extended improvisational jams that weave through their originals and some carefully selected covers that they make all their own. (Browse group: Live Music)
  • Moonstone Riders at 5:30, 9:00 & 11:00 — October 3, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30. Come join Moonstone Riders on a rock’n ‘roll journey through a twangy world of psychedelic funk! The band features Matt Benfield on guitar and vocals, Marcia Winslow on vocals and percussion, and Jeffrey James on bass and vocals. The Riders, from Naples, FL, are known for their energetic live shows, which often feature extended improvisational jams that weave through their originals and some carefully selected covers that they make all their own. (Browse group: Live Music)
  • 11th Annual Jerry Garcia Birthday Bash — October 4, 2026 · 1:00 PM – 7:00 PM · Green Parrot Bar: Join us for the 11th Annual Jerry Garcia Birthday Bash! Stay tuned for more details! Join us for jams by the Grateful Dead played live by The Happy Dog, good vibes, a silent auction, and more! This daytime event is all about enjoying music and supporting a great cause. Proceeds support Reef Relief’s Education and Conservation programs. We’ve just reached 100,000 students - help us reach the next 100,000 by coming out and jamming to Grateful Dead tunes and more! (Browse group: Live Music)
  • The Happy Dog at 5:30 & 7:30 — October 6, 2026 · 5:30 PM – 9:30 PM · Green Parrot Bar: Two Set Tuesday throughout September with The Happy Dog. 5:30-7:00 and 7:30-9:30. (Browse group: Nightlife)
  • Sunset Celebration — October 7, 2026 · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Goombay Festival — October 7, 2026 · Bahama Village: A vibrant celebration of Bahamian culture with music, food, and colorful parades in Bahama Village. (Browse group: Festivals)
  • Leap of Faith at 5:30, 8:30 & 10:30 — October 8, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00, and 10:30-12:00 Psychadelic country with an Island twist (Browse group: Nightlife)
  • Guavatron at 5:30, 9:00 & 11:00 — October 9, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Guavatron, keeping their roots of dance, rock, electronica, and funk alive. Expect smooth jams with hard-hitting peaks of musical ingenuity. (Browse group: Live Music)
  • Guavatron at 5:30, 9:00 & 11:00 — October 10, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Guavatron, keeping their roots of dance, rock, electronica, and funk alive. Expect smooth jams with hard-hitting peaks of musical ingenuity. (Browse group: Live Music)
  • Guavatron Soundcheck Set — October 11, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute sets: 5:30-7:00 Guavatron, keeping their roots of dance, rock, electronica, and funk alive. Expect smooth jams with hard-hitting peaks of musical ingenuity. (Browse group: Live Music)
  • The Happy Dog at 5:30 & 7:30 — October 13, 2026 · 5:30 PM – 9:30 PM · Green Parrot Bar: Two Set Tuesday throughout September with The Happy Dog. 5:30-7:00 and 7:30-9:30. (Browse group: Nightlife)
  • Dr. Bacon at 5:30, 8:30 & 10:30 — October 14, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00, and 10:30-12:00 Founded in the streets, bars and unhinged house parties of Boone est. 2013, Dr. Bacon is a Funked Up Appalachian Rock band currently based in Asheville, NC. Dr. Bacon is: Myles Dunder- Vocals, Saxophones, Guitars John Kirby- Lead Guitar & Vocals Ben New- Drums, Percussion, Vocals Matt Gornto- Bass (Browse group: Live Music)
  • DJ Logic & EBY at 5:30, 8:30 & 10:30 — October 15, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: Electric Blue Yonder: 5:30-7:00 DJ Logic w/ EBY: 8:30-10:00 DJ Logic Set: 10:30-12:00 (Browse group: Live Music)
  • Xperimento at 5:30, 9:00 & 11:00 — October 16, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Goombay Weekend! Help us kick off our neighborhood’s Goombay festivities off with Xperimento making their much-anticipated return. And as we all know, on Sunday, Goombay weekend finishes up and Fantasy Week begins with The Zombie Bike Ride, the local-centric brain-eating extravaganza that includes a Green Parrot Zombie Bike Ride After-Party with Xperimento! Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Miami’s explosive, Grammy-nominated, 7-piece Latin funk fusion band. Think cumbia, reggae, salsa, funk, rumba, and dub! A Parrot favorite time and time again! (Browse group: Festivals)
  • 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)
  • Xperimento at 5:30, 9:00 & 11:00 — October 17, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Goombay Weekend! Help us kick off our neighborhood’s Goombay festivities off with Xperimento making their much-anticipated return. And as we all know, on Sunday, Goombay weekend finishes up and Fantasy Week begins with The Zombie Bike Ride, the local-centric brain-eating extravaganza that includes a Green Parrot Zombie Bike Ride After-Party with Xperimento! Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Miami’s explosive, Grammy-nominated, 7-piece Latin funk fusion band. Think cumbia, reggae, salsa, funk, rumba, and dub! A Parrot favorite time and time again! (Browse group: Festivals)
  • Xperimento Zombie Bike Ride Afterparty — October 18, 2026 · 7:00 PM – 11:00 PM · Green Parrot Bar: Two 90-minute sets: 7:00-8:30 and 9:00-10:30 (times may change). Miami’s explosive, Grammy-nominated, 7-piece Latin funk fusion band. Think cumbia, reggae, salsa, funk, rumba, and dub! A Parrot favorite time and time again! (Browse group: Live Music)
  • The Beatle Band at 5:30, 9:00 & 11:00 *Offical Fantasy Fest Event — October 19, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, re-create a Fab Four Show with "THE BEATLE BAND, All You Need is Love" with shows at 5:30, 9:00 and 11:00pm. Their past Beatle Tribute Shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang along to a set-list pulled from decades of Lennon-McCartney hits. Photo Credit: Bill Klipp (Browse group: Festivals)
  • 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)
  • Igor And The Red Elvises 5:30, 9:00 & 11:00 — October 20, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 It’s the return of "Your Favorite Band!", Siberian Surf-Rockers Igor and The Red Elvises, two days and nights of their unique blend of Russian folk music, 50’s rockabilly, surf, reggae, and whatever-else-makes-them-happy! (Browse group: Live Music)
  • Fantasy Fest — October 21, 2026 · Duval Street: An annual 10-day festival featuring costume parades, parties, and themed events culminating in a grand parade. (Browse group: Festivals)
  • Igor And The Red Elvises 5:30, 9:00 & 11:00 — October 21, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 It’s the return of "Your Favorite Band!", Siberian Surf-Rockers Igor and The Red Elvises, two days and nights of their unique blend of Russian folk music, 50’s rockabilly, surf, reggae, and whatever-else-makes-them-happy! (Browse group: Live Music)
  • 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)
  • FUNK IT UP Party with Trae Pierce & The T-Stones at 5:30, 9:00 & 11:00 *Official Fantasy Fest Event — October 22, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Festivals)
  • Sunset Celebration — October 22, 2026 · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • 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)
  • Trae Pierce & The T-Stones at 7:00, 9:00 & 11:00 — October 23, 2026 · 7:00 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 7:00-8:30, 9:00-10:30, and 11:00-12:30 set times could change Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Live Music)
  • Trae Pierce & The T-Stones at 5:30, 9:00 & 11:00 — October 24, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 (times may change). Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Live Music)
  • 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)
  • Waynard Scheller and Rainbow Full of Sound at 5:30, 8:30 & 10:30 — October 27, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 and 10:30-12:00. Waynard Schiller and Rainbow Full of Sound, one of the East Coast’s premiere Grateful Dead tribute bands, who have made re-creating precise sets from the Dead’s legendary appearances their mainstay, particularly the twenty-one memorable shows of Dead’s European tour in 1972 will appear at The Green Parrot (Browse group: Live Music)
  • Waynard Scheller and Rainbow Full of Sound at 5:30, 8:30 & 10:30 — October 28, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 and 10:30-12:00. Waynard Schiller and Rainbow Full of Sound, one of the East Coast’s premiere Grateful Dead tribute bands, who have made re-creating precise sets from the Dead’s legendary appearances their mainstay, particularly the twenty-one memorable shows of Dead’s European tour in 1972 will appear at The Green Parrot (Browse group: Live Music)
  • Fantasy Fest Parade — October 29, 2026 · Duval Street: The grand parade of Fantasy Fest featuring elaborate floats, costumes, and entertainment throughout Duval Street. (Browse group: Festivals)
  • Key West Farmers Market — October 29, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring local produce, crafts, and artisanal goods. (Browse group: Food & Drink)