Key West Events Calendar

Find upcoming Key West festivals, concerts, live music, cultural events, celebrations, and other things to do in Key West, Florida.

Featured Key West Events

  • 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 9–13, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events. (Browse group: Festivals)

Upcoming Events

  • Sunset Celebration — September 2, 2026 · 6:29pm · Mallory Square: Enjoy the vibrant atmosphere at Mallory Square during the Sunset Celebration, where you can watch the sunset while enjoying live entertainment. (Browse group: Community)
  • Gulfstream Band — September 2, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Summer Bingo Night (Free Entry) — September 2, 2026 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Stephanie Ryann — September 2, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • The Local Discounts — September 2, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Monthly Ukulele Night — September 2, 2026 · 8:00 PM – 11:00 PM · Green Parrot Bar: The Green Parrot Ukulele Association will hold their monthly meeting with co-hosts Bobby Howard, Wavy Dave, and bassist Bubba Lownote. Following the same format as the previous well-attended, high-spirited shindigs, the meeting will begin with a workshop at 8 p.m. for those just starting out on theinstrument. Basic instruction and chord and song sheets will be provided. At 9 p.m., there will be featured performers, an open mic and a play-along, in no particular order. For those who missed last month’s’s meeting, it was outstanding, with an ever-growing congregation of uke-bearing aficionados in attendance, most of whom crowded the stage for a few nimble and professional sing-along covers of popular songs to wrap up an already lively night. “It is obvious from recent month’s turnouts that there is a serious Key West ukulele scene simmering just below the surface,” said John Vagnoni, Green Parrot manager. “We also see this as a unique way for Key Westers to meet people and make music at the same time.” Dig out that old ukulele from your attic or closet and strum your way into a four-string stupor at Green Parrot Ukulele night, Key West’s only ukulele-powered jam session. Come to just listen or join in. All levels are welcome and remember, spare ukes and instruction are available for those who want to try them out. (Browse group: Live Music)
  • John Frinzi & Aaron Scherz — September 2, 2026 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Jess and Jill Trio — September 3, 2026 · 5:30 PM – 11:00 PM · Green Parrot Bar: Two sets: 5:30-7:00 and 9:00-11:00 Jesse Wagner and Jillian Todd bring us sweet originals and harmonic covers. They won Duo Of The Year at the 2024 Iggies, Key West Music Awards. (Browse group: Live Music)
  • The Local Discounts — September 3, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Sharese — September 3, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • 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)
  • Key West Farmers Market — September 3, 2026 · 1:00pm - 6:00pm · Truman Waterfront: Visit the Key West Farmers Market for fresh produce, local goods, and handmade crafts every Thursday. (Browse group: Food & Drink)
  • Gulfstream Band — September 3, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • John Frinzi & Aaron Scherz — September 3, 2026 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Gulfstream Band — September 4, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • The Local Discounts — September 4, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Just a Few Friends Event feat. Gypsies in the Palace — September 4, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Steeln' Peaches at 5:30, 9:00 & 11:00 — September 4, 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 Steeln' Peaches: an Allman Brothers Revue makes their much anticipated return to the Green Parrot stage. Paying tribute to the founding fathers of Southern rock and Spearheaded by Chuck Magid, whose incorporation of barn-burning lap-steel slide guitar gave the group inspiration for its name, “Steeln' Peaches-The Music of the All man Brothers Band" features some of Florida’s most exciting young musicians with Daniel Heitz, guitar, vocals; Aaron “Bucky” Buckingham, drums, vocals; Glenn Kastrinos, bass, vocals; Colin Fei, keyboards, vocals; and David Vanegas, percussion, vocals. (Browse group: Live Music)
  • Sunset Celebration — September 4, 2026 · 6:27pm · Mallory Square: Join the crowd at Mallory Square for the Sunset Celebration, a beloved Key West tradition with entertainment and local crafts. (Browse group: Community)
  • Cliff Cody — September 5, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • 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)
  • Just a Few Friends Event feat. Gypsies in the Palace — September 5, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
  • Steeln' Peaches at 5:30, 9:00 & 11:00 — September 5, 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 Steeln' Peaches: an Allman Brothers Revue makes their much anticipated return to the Green Parrot stage. Paying tribute to the founding fathers of Southern rock and Spearheaded by Chuck Magid, whose incorporation of barn-burning lap-steel slide guitar gave the group inspiration for its name, “Steeln' Peaches-The Music of the All man Brothers Band" features some of Florida’s most exciting young musicians with Daniel Heitz, guitar, vocals; Aaron “Bucky” Buckingham, drums, vocals; Glenn Kastrinos, bass, vocals; Colin Fei, keyboards, vocals; and David Vanegas, percussion, vocals. (Browse group: Live Music)

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