More Than a Calendar: Plan Your Night Out in Key West and the Florida Keys
LiveMusicEveryDay.com is more than a live music calendar. Here is how to use it to plan your night out in Key West and the Florida Keys.
I overheard someone call the Green Parrot a dive bar, and I agreed, just not the way they meant it. Some folks say dive because it may look like there is no AC, or because shorts and tank tops are no problem and nobody makes a fuss. Fair enough.
Here is my version. Except for the bartender, nobody is likely to talk to you unless you talk first. Yup, you are left alone at the Parrot, and what a gift that is.
Far from a dive, it is more like The Bar.
Add music that makes you dance, bartenders who never leave you hanging (they keep the drinks coming, because you want them to), and a popcorn machine that never stops popping, so there is always fresh popcorn.
The Parrot has kept good live music going on Whitehead Street in Key West for years, and October is when it shows off. This month’s calendar is a big one. Here is the month, and why this corner of the island matters.
It is also where the stories happen. Six of us once sat side by side on the bar stools working through root beer floats with Patrick and Andy our signature request shot – 30+ years ago – I hear this shot is still going strong late night. In those days Jägermeister was king … what’s it now, Tequila? Jäger bombs were a throwback to my Penn State days. Erika swears they were root beer barrels. It was a long time ago, so call it a tie.
The Parrot’s own cultural calendar puts it plainly: no cover, no minimum, no wonder. Here is the month, darling, in order of appearance.
First weekend (Oct 1–4). Local favorites Good Trees River Band open the month on Thursday, then the Moonstone Riders roll in Friday and Saturday with swampy, psychedelic funk and long improvisational jams. Sunday afternoon (1–7 PM) is the 11th annual Jerry Garcia Birthday Bash and Reef Relief Benefit, a marathon Grateful Jam with The Happy Dog, a local band. The Parrot says the bash is running late this year, and the money goes to Reef Relief’s education and conservation work.
Second week (Oct 5–11). Monday bingo, The Happy Dog, Ukulele Night on Wednesday, and Leap of Faith on Thursday. Then Guavatron, a South Florida band that mixes dance, rock, electronica and funk, plays Friday and Saturday, with a Sunday set after Jess & Jill & Chase‘s afternoon show.
Third week, and a double feature (Oct 12–15). After Sister Season Bingo and another Happy Dog night, the Parrot books two special nights for its regulars. Wednesday is Dr. Bacon from Asheville, North Carolina, for funked-up roots and rock ‘n’ roll. Thursday brings three sets: Electric Blue Yonder, a collaborative set with DJ Logic, then a late set of DJ Logic spinning solo.
Goombay weekend and Zombie Fest (Oct 16–18). Miami’s Grammy-nominated seven-piece Latin/funk band Xperimento plays the Parrot stage Friday and Saturday. On Sunday the Zombie Bike Ride lands at the Parrot for an after-party, and Xperimento is back for a late “Dance With the Dead” set (7 and 9 PM on the calendar), after Cayman & Company in the afternoon.
Fantasy Fest week (Oct 19–25). It starts Monday with Tony Baltimore and his Beatle Band re-creating a Fab Four show. Igor and the Red Elvises, Siberian surf-rockers with a mix of Russian folk, rockabilly, surf and reggae, take Tuesday and Wednesday. Thursday is the Funk It Up! party with five-time Grammy winner Trae Pierce & The T-Stones, who then stay through Friday and Saturday. Per the Parrot, stop in after the Old Town Masquerade March on Friday, and grab a front-row seat for the Fantasy Parade on Saturday night.
The last stretch (Oct 25–31). Sam Carlson Sound and The Happy Dog (two sets) fill Sunday, bingo returns Monday, and Waynard Scheller’s Rainbow Full of Sound, one of the East Coast’s premier Grateful Dead tribute bands, plays Tuesday and Wednesday. Luffkid & Friendz are on Thursday, and Funk You from Augusta, Georgia, play Friday and Saturday to carry the month into HalloWeekend.
Between the big names, the Parrot leans on the island’s own. The calendar sprinkles in Good Trees River Band, Leap of Faith, Jess & Jill & Chase, Cayman & Company, Luffkid & Friendz and Sam Carlson Sound, which is the local-talent mix that makes a visitor feel like a resident by the second beer.
Then come the cultural extras. Green Parrot Ukulele Night is billed as Key West’s only uke-powered jam session. Monday Night Bingo is 100 percent for charity, with the Rotary Club of Key West, Sister Season and the Key West Art & Historical Society each hosting a Monday. Add sets from The Happy Dog, and you have some cool autumn action for visitors and locals alike.
No Parrot October is complete without its Crown Jewel: the Annual Halloween Costume Party and Contest, Saturday, October 31, with Funk You at 9 PM. The Parrot calls it the 52nd annual, “we think!”, and explains the hedge. Their longtime owner knows for sure a party happened in 1974, right after he arrived in Key West, but cannot say whether the Parrot threw one in the years before that, so 1974 is the yardstick.
Plan your visit: every show above is free. See the full lineup on the Green Parrot’s page on LMED, and find more live music every day of the week on the LMED calendar. Times can change, so check the Parrot’s own posts before you head out.
LiveMusicEveryDay.com is more than a live music calendar. Here is how to use it to plan your night out in Key West and the Florida Keys.
KEY WEST • OCTOBER 2026 Our October artwork celebrates musical imagination. Your gigs bring it to life. Upload your October scheduleView Key West’s live music calendarEmail your schedule Key West […]
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