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Fantasy Fest countdown | 10 tips — plus one — for enjoying the festival like a local

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.

10/16/2019

Fantasy Fest 2019 is a bit like an aging, 55-year-old Gen Xer getting her groove on by pretending to be, well, 30-something again. Back in 1979, Baby boomers, the ancient parents of today’s sagging Xers and scared to death they and their businesses would disintegrate during the long, slow months between hurricane season and January, created Fantasy Fest as a Halloween to end all Halloweens — and to get the tourists back in town with super-sized wallets and generous tips.

Four Key West locals, Frank Romano, Joe Liszka, Tony Falcone and Bill Conkle, created the two-day party and parade. It worked. For 40 years, hundreds of thousands of folks believing in Halloween, the Key West mystique and what-goes-on-in-Key-West-stays-etc., descend on the island for the last two weeks of October for 10 days that culminate in a spectacular parade featuring the King, Queen and Court of Fantasy Fest.

Most who come spend money, fill up restaurants and beds and generally forget that despite their aging years, boobs and private parts — even with gloppy paint and a smear of glitter — ought not be spreading across a bench alongside the Truman Waterfront Park. I really hate having to bring a pack of Handi Wipes when out and about between Oct. 17 and Oct. 27. But, ewwww, I mean who wants to sit where a stranger’s naked be-hind has been?

It’s easy for locals to hate on Fantasy Fest. Hordes of off-islanders swarm across the island’s tourist district, too many of them day trippers with coolers and camp chairs and not a dime to spend. Equal hordes of those who fancy themselves “swingers” go in search of lewd, weird and things you generally don’t want to explain to your grand kids or employers. Thank heaven today’s event producer, Nadene Grossman Orr, has corralled the worst of the stuff into something they’re calling the Little Black Book. Look it up. Everyone else can get info and schedules at the official Fantasy Fest website. (OK, so PS: You can find the black book skeds there, too.)

What started as a locals parade and some partying morphed into 50,000-75,000 off-islanders pouring into Key West, bent on having an outrageous time — and a few years ago things got just too darn raunchy and the local hullabaloo forced enough changes to ensure Fantasy Fest was more festival and less fantasy of the weird. Key West may well be “Where the Weird Go Pro,” but most of us keep most of our clothes on when we go to Publix. At least the tutu covers appropriate parts.

Yeah, it’s easy to hate on Fantasy Fest. The fact is, those boomers in 1979 were right. This is, hands down, the slowest time of the year. While I love that I don’t need a reservation and locals get discounts, no business large or not-so, can survive on October cash flow. So, on Oct. 17, Key West kicks off Fantasy Fest 2019, 40 years of being “In Tune, But Off Key.”

If you’re coming down this year — or next — or if you’re a local wondering if you should brave the hordes again to see if things have gotten any better, here are 10 tips for creating your own Fantasy Fest dance card:

  • Stay out of tourist town: For the most part, stay off Duval. Especially in the middle and lower blocks. That’s where far too many naked people and day trippers converge. There’s really nothing inspiring about bad body paint, sagging codpieces, cellulite buttocks and drunks staggering up the steps of St. Paul’s cathedral. And, yeah, I know they’re not supposed to do that. But they do.
  • Go where tourists don’t: Do sunsets and sunrises at the White Street Pier or the Truman Waterfront Park. Free. No crowds. Perfectly splendid views. And pretty much too far off the beaten tourist paths to attract the off-island curious. Wear a tutu and headdress with your shorts and flips to Fort Zachary Taylor State Park on Oct. 22, the official Tutu Tuesday day. You’ll giggle. Folks will glance. No one will think you the least bit odd. As long as you’re wearing a swimsuit under the tutu.
  • Goombay Festival: Celebrate Key West’s Bahamian roots with food, entertainment and island arts and crafts in Bahama Village. Starts Friday, Oct. 18, and extends into Saturday. Main entertainment stage is located at the corner of Petronia and Fort Street and features nonstop musical entertainment ranging from gospel to reggae. Family friendly and continues on Saturday! Noon to midnight.
  • Zombie Bike Ride: The Zombie Bike Ride didn’t start out as an official Fantasy Fest event, but it didn’t take long for this 2010 ride to grow from a couple hundred to more than 7,000 costumed zombies on bikes. Grab your grungy gear and fake blood, hop a bike and pedal with the best of them. Or do what smart locals do, especially if they’ve been-there-done-that-ride before: Ditch the riding, wear the costume, bring a camp chair and cheer for your favorite zombies as they pedal past. There are some terrific viewing spots along Atlantic Boulevard. Bring your beverages of choice. Get there by 6:30 p.m. Oh, and don’t forget sun glasses. It can be kinda glare-y.
  • Support the Royal Court: Fantasy Fest helps raise money for AH Monroe, the decades-old, local not-for-profit that started as AIDS Help and has both continued its original mission and expanded to provide the services needed today. Two great events ought be on your locals dance card: The Royal Retrospective by the Key West Art and Historical Society, which runs through Oct. 20, at the Custom House Museum and the Royal Coronation Ball on Oct. 18. Both benefit AH Monroe. The ball features local entertainment, the candidates for the court and food and beverages — and the winners for King and Queen are announced, crowned and feted. This is what the folks at KWAHS say about the retrospective exhibit: “The Royal Retrospective exhibit is co-curated with Tennessee Williams Key West Exhibit founder Dennis Beaver and will focus on the themes from each year’s celebration via the annual Fantasy Fest posters, photographs of the former Kings and Queens, the fundraising efforts on behalf of AH Monroe, and the diverse objects and images that make Key West the place to be each October. This year is extra special because Fantasy Fest organizers have donated a large number of historical ephemera and photographs to The Society that will be on display.”
  • Pet Masquerade: Make a matching tutu and headdress for your dog because even if you don’t compete, you’ll want to watch the absurdly nuts Pet Masquerade Oct. 23, at the amphitheater at Truman Waterfront Park. (Cat lovers: Consider borrowing a neighbor’s dog. No respectable cat even goes OUT during Fantasy Fest. And, they assuredly will not tolerate tulle.)
  • Headdress Ball: Get ready for the 37th Annual Headdress Ball, Oct. 24, at the waterfront amphitheater. You don’t have to wear a headdress, but, heck, it’s Key West, so why not? The Key West Business Guild’s premier LBGTQ+ event combines over 20 magnificent headdress competitors, entertainment (think Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show) for a spectacle that will leave you happy at the end of the evening. ide your bike. Beat the crowds getting home.
  • Locals Masquerade March: Unpack your costume — or at least sort out some decent walking shoes — for the annual locals parade on Oct. 25. The Masquerade March lines up on Frances Street near the cemetery and winds its way across Fleming and Simonton through Old Town and then to Duval. The march has perhaps the shortest description on the Fantasy Fest website — and it’s THE best locals deal on the island. No cost. Join the march — in costume or not — at any point along the way. Stop and talk with neighbors and friends. Run to catch up or drop out at any time. Every house along the way is hooting and hollering and wishing you well. Thousands of friends and neighbors are a perfect march or perfect watch. Oh, so you’re not local? That’s OK. No one is checking IDs. Just don’t be a jerk.
  • Do the Fantasy Fest Parade: You have to see this thing at least once every few years, so brave the crowds, the body paint, the naked ones — who despite the rules still don’t get it and there aren’t enough cops to enforce covering up — and find a place to watch the extravaganza of music, lights, music and all-things-parade. Pray for cool weather, because there’s nothing more stifling than being in the Fantasy Fest crowd. Parade steps off at 7 p.m., Saturday, Oct. 26. That 7 p.m., start time means two things: It’s still daylight so you won’t get the full effect of floats with lights until after dark around 8 p.m. And, it means you’ll be watching the parade for hours to come. Stay on the east side of Duval or you’ll have a tough time getting back home if you live that way. Better still, don’t sweat the “lights are better” idea and instead stakeout a viewing spot over on Whitehead around the courthouse. Get to see the parade before everyone is exhausted and while things are moving pretty smoothly. And, you can head for home the back way.
  • Sunday when it’s all over: There’s always the Tea Dance at La Te Da. Or you can invite your friends and neighbors over for something on the grill. And a toast to each other that you once again survived Fantasy Fest.
  • Just stay home. Nah.

 

 

 

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Linda Grist Cunningham

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.

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