Key West Festivals

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

  • Good Trees River Band EARLY Soundcheck 5:00-7:00 *Pre Amp Show* — September 30, 2026 · 5:00 PM – 7:00 PM · Green Parrot Bar: One set: 5:00-7:00 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)
  • 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)
  • 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)
  • 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)
  • 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)
  • 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)
  • 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)
  • 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)
  • 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)
  • Fantasy Fest Closing Party — October 30, 2026 · Duval Street: A final celebration to close out the Fantasy Fest with music, dancing, and festivities. (Browse group: Festivals)
  • Key West Film Festival — November 9, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)
  • Key West Film Festival — November 10, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)
  • Key West Film Festival — November 11, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)
  • Key West Film Festival — November 12, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)
  • The Resolvers at 5:30, 9:00 & 11:00 — November 13, 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 The Resolvers Bring “Big Band Reggae” to Green Parrot. Named the Best Reggae band of 2013 by The Ft Lauderdale New Times, The Resolvers draw influences from classic Jamaican Reggae, Rocksteady, and Ska along with American Rock, Jazz, Funk, and Soul. Their live show has been described as explosive with up to 10 musicians on stage, including a full horn section, and led by the powerful brother & sister duo of Ojay & Sahara Smith on lead vocal roles. The Resolvers play in the style they coined “Big Band Reggae” combining classic jamaican roots and lively new orleans stylings. Siblings Ojay & Sahara Smith (son and daughter of Ernie Smith) both take turn on lead vocals roles and the band features a 4 piece horn section. Their show has been described as “explosive” and “must see”, and the band has gained the reputation as a premier reggae act. The Resolvers have shared the stage with The Wailers, Julian Marley, Stephen Marley, Damian Marley, Kymani Marley, Inner Circle, English Beat, Yellowman, Matisyahoo, Lee ‘Scratch’ Perry, Mishka along many other world renowned acts in major International festivals such as Marley Fest, Jamaican Jazz & Blues Fest, Sun Fest, Aura Music & Arts Fest, Dub Fest and more. (Browse group: Festivals)
  • Key West Film Festival — November 13, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)
  • The Resolvers at 5:30, 9:00 & 11:00 — November 14, 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 The Resolvers Bring “Big Band Reggae” to Green Parrot. Named the Best Reggae band of 2013 by The Ft Lauderdale New Times, The Resolvers draw influences from classic Jamaican Reggae, Rocksteady, and Ska along with American Rock, Jazz, Funk, and Soul. Their live show has been described as explosive with up to 10 musicians on stage, including a full horn section, and led by the powerful brother & sister duo of Ojay & Sahara Smith on lead vocal roles. The Resolvers play in the style they coined “Big Band Reggae” combining classic jamaican roots and lively new orleans stylings. Siblings Ojay & Sahara Smith (son and daughter of Ernie Smith) both take turn on lead vocals roles and the band features a 4 piece horn section. Their show has been described as “explosive” and “must see”, and the band has gained the reputation as a premier reggae act. The Resolvers have shared the stage with The Wailers, Julian Marley, Stephen Marley, Damian Marley, Kymani Marley, Inner Circle, English Beat, Yellowman, Matisyahoo, Lee ‘Scratch’ Perry, Mishka along many other world renowned acts in major International festivals such as Marley Fest, Jamaican Jazz & Blues Fest, Sun Fest, Aura Music & Arts Fest, Dub Fest and more. (Browse group: Festivals)
  • Pirates in Paradise — November 19, 2026: A week-long festival celebrating the pirate heritage of Key West with parades, parties, and family-friendly activities. (Browse group: Festivals)
  • Pirates in Paradise — November 20, 2026: A week-long festival celebrating the pirate heritage of Key West with parades, parties, and family-friendly activities. (Browse group: Festivals)
  • Pirates in Paradise — November 21, 2026: A week-long festival celebrating the pirate heritage of Key West with parades, parties, and family-friendly activities. (Browse group: Festivals)
  • Ajeva at 5:30, 9:00 & 11:00 — November 27, 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 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • Ajeva at 5:30, 9:00 & 11:00 — November 28, 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 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • Ajeva Soundcheck Set — November 29, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • Key West Songwriters Festival — March 1, 2027: An annual festival celebrating the craft of songwriting with performances by various artists. (Browse group: Festivals)
  • Conch Republic Independence Celebration — April 23, 2027 · Duval Street: A quirky celebration of Key West's independence with parades, parties, and various festivities. (Browse group: Festivals)
  • Key West Songwriters Festival — May 3, 2027: An annual festival celebrating songwriters with performances and workshops throughout Key West. (Browse group: Festivals)
  • Key West Songwriters Festival — May 4, 2027: An annual festival celebrating songwriters with performances and workshops throughout Key West. (Browse group: Festivals)
  • Key West Songwriters Festival — May 5, 2027: An annual festival celebrating songwriters with performances and workshops throughout Key West. (Browse group: Festivals)
  • Key West Songwriters Festival — May 6, 2027: An annual festival celebrating songwriters with performances and workshops throughout Key West. (Browse group: Festivals)
  • Key West Songwriters Festival — May 7, 2027: An annual festival celebrating songwriters with performances and workshops throughout Key West. (Browse group: Festivals)
  • Key West Pride — June 1, 2027: A week-long celebration of the LGBTQ+ community featuring parades, parties, and various events throughout Key West. (Browse group: Festivals)
  • Key West Pride Parade — June 3, 2027 · 5:00pm · Duval Street: Join the vibrant parade celebrating love and acceptance as it marches through the streets of Key West. (Browse group: Festivals)
  • Hemingway Days — July 21, 2027 · Sloppy Joe's Bar: Celebrate the life and works of Ernest Hemingway with literary readings, a short story competition, and various events at Sloppy Joe's Bar. (Browse group: Festivals)