The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

October in Key West Fantasy Fest

October in Key West | Five tips for transition month

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


October in Key West is transition month. We use these 31 days to slide from summer into season (no one calls it winter because, well, winter as a marketing concept includes snow and Key West has never seen so much as frost. Snow would be out of the question.)

October in Key West is hot and humid until it’s not. That was this past week. Porch pounding rain on Monday, followed by clear skies and a coolish breeze on Tuesday. Everyone knows that it’s time to dig out the long sleeves and socks and give them a good wash for the 17 times we will wear them over the next six months.

Did you know you can tell when a not-from-here moved to Key West by the style of their winter wear? OK, so that’s kind of an insider joke, but there’s some truth there. My boots, gloves, hat and ski jacket (not plural; one needs only one) bear a startling resemblance to clothing cuts and colors of the wayback times. No one cares, of course, because we only wear them when the temperatures drop into the mid 70s during the day.

I keep handy a mink coat I bought secondhand in the early 1990s. Not to wear; that would be weird even for Key West. But to throw across the bed when nights get really cold; like 65 or so. I think I’ve dragged it out once, though the Cat 5s do enjoy it.

Anyway, back to October in Key West. Even without a calendar in front of me, I’d know it is October. Here’s how:

Key West Parking Sticker October in Key West
Time to order your parking sticker online. It’s much easier this year. And, yes, you can still go to City Hall in person.

Here’s how I know it’s October in Key West

  • The weather. We’ve covered that. See above. Summer’s not done with us, but close. A friend who stopped by for coffee this week was wearing a SWEATSHIRT. With long sleeves and a hood, although the hood was more decorative than functional.
  • The (sorta) end of hurricane season, but I’m not dismantling the prep boxes. Hurricane season ends Nov. 30, but we don’t have as many “do we go or do we stay” discussions and I’m not obsessively scouring the west coast of Africa or researching Sahara dust. That’s good news of a sort for locals drying out from Hurricane Ian flooding — and even better news for Florida’s southwest coast, which never’s going to get back to normal. Oh, they’ll rebuild; there’s no stopping that development juggernaut no matter how much it shouldn’t happen. But at least there’s a chance to get things cleaned up and cleared away without facing down another storm. I just wouldn’t hold my breath. November 30 is a long stretch.
  • Key West parking permits go on sale. The Key West residential parking sticker is a coveted island perk. Always a colorful design (this year’s is the Southernmost Buoy), the sticker is an at-a-glance visual clue that one belongs here. It says the vehicle is owned by someone who has made a long-term commitment to the island of Key West. Some folks opt out of removing old stickers, lining them up in a conga dance up and down the windshield. We wear those stickers with pride — and we get some free parking to boot. The best way to renew is online; I did it and the sticker arrived this week. Way easier than last year’s semi-debacle that started with reversing the decision to have NO stickers and then waded through a website interface that wasn’t user friendly to say the least. It’s not perfect yet, but much improved.
  • So, how’s it looking for season? October signals the annual speculation about how busy things might be for season. Since Covid’s first October in 2020, I’ve predicted everything from “season is dead; we’ll be a ghost town” to “Mary, Joseph and the Wee Donkey, where did all these people come from.” I’m predicting this season will be busy-busy but not-off-the-rails worse than last year. What will make this season challenging is figuring out how to serve and entertain those maddeningly happy visitors who expect premo service from a work force filled with ever increasing staffing gaps. Oh, and all those now-displaced snowbirds and visitors to the likes of Fort Myers, Sanibel and surrounds? We might get a few, but folks who winter there aren’t going to think Key West makes sense.
  • And, then there is the mother of all October, the 43rd annual Fantasy Fest. Almost two weeks of parades (pets, people, bikes and zombies), food, entertainment, elaborate costumes, headdress balls and king and queen coronations — and what my grandson calls “wrinkly people” decked out in a feather and not much else. It’s a bazillion dollar revenue stream that one loves, hates or cherry-picks. I stay four or five blocks off Duval. Close enough to say I went without slithering against gooey heat-melted body paint. It is October in Key West, after all.

Photo by Carol Tedesco

Prepping for the Parade: 

Fantasy Fest 2022 kicks off Oct 21, and creators like Daniel Bitnar, pictured here with sketches and costume pieces for this year’s  “Cult Classics & Cartoon Chaos” themed extravaganza, are already up to their beads, feathers, and baubles in preparation. Since 2010, Bitnar has been designing and creating dazzling, take-your-breath-away costumes for himself and his team, and winning a string of top prizes at events including Headdress Ball, Pretenders in Paradise, the Masquerade March, and the Fantasy Fest Parade. Fantasy Fest 2022 is presented in part by the Monroe County Tourist Development Council. (Photo: Carol Tedesco/


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