September 2026 Key West Events & Festivals

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

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)
Sunset Celebration — September 5, 2026 · 6:26pm · Mallory Square: Don't miss the Sunset Celebration at Mallory Square, where you can enjoy live music, food vendors, and the breathtaking sunset. (Browse group: Live Music)
Gulfstream Band — September 5, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
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)
Gulfstream Band — September 6, 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 6, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
McKenna Carlson — September 6, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
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)
Jess and Jill at 12:00 & 2:00 — September 6, 2026 · 12:00 PM – 4:30 PM · Green Parrot Bar: Two 90-minute sets: 12:00-1:30 and 2:30-4:00 (ish) 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)
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)
Zack Seemiller — September 7, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Mark King Duo — September 7, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Womenfest — September 7, 2026: Womenfest continues with more events and activities celebrating women in the beautiful setting of Key West. (Browse group: Community)
Ivan Duke Band — September 7, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Harley Ray — September 8, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Mark King Duo — September 8, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)