Nightlife » Parties

Fools in Frocks: The Fire Island Labor Day Drag Party

by Bobby McGuire
EDGE Media Network Contributor
Tuesday Aug 20, 2013

Of the five senses, sound almost never signifies the changing of seasons. That is, of course, unless you're in Fire Island Pines, where each year in early September, the gentle signature boardwalk song of neoprene sandals is replaced by the more raucous "click and clomp" drumming of double-digit-sized pumps. There is no need to consult the "gay farmers' almanac" as that sound signifies only one thing: the annual "Fool's Paradise Labor Day Drag Party" and the coming of fall.

"What's a bunch of creative gay men in the Pines do to when they want to spruce up their schedule of beach, drinking and dancing?" says Chiquita Moskowitz (a nom de drag), one of the party's founding attendees and a member of Fire Island Pines' long-standing floating house aptly named "Fool's Paradise." "Our answer was to turn one of our Saturday-night dinners into a drag affair."

It all started in a small (by Fire Island Pines' standards) two-bedroom house in late July 1996, when Moskowitz and company decided to transform their regular house supper into a drag dinner. From its humble beginnings, the gender-bending gathering has turned into one of the biggest and most eagerly anticipated parties on Fire Island, with a cross-dressed crowd exceeding 500 guests annually all decked out to fit a theme unique to each year.

A Labor Day weekend tradition since 1998, the Fool's Paradise Drag Party is distinct in more manners than dress code. Unlike nearly all of the over-the-top parties held weekly in The Pines, with equally over-the-top admission price tags, all that is required at the gate for the Fool's fancy dress fete is drag - hopefully taken to some serious extremes.

As stated on the event's website (created in 2008 after the party grew to a point requiring one): "We proudly tell our guests that we don't charge admission; we only ask that you dress up - Drag is mandatory! The spirit of the party is rooted in our guests coming together and challenging their comfort zone in a safe, fun environment. It doesn't work if some people come in costume and others just come to stare at the people in costume."


Although Fire Island can’t claim bragging rights for inventing the idea of a "theme party, it can largely be credited for perfecting the concept. Since 1999, the Labor Day Drag Party has expected guests to show up not only in drag but in drag specific to each year’s unique theme. Fourteen years later, traffic has stopped on the Pines’ boardwalks to make way for an annual parade of fairy princesses, disco divas, bridesmaids, housewives, models, toy dolls, stewardesses, and all manner of working women, each on their way to a carefully planned red-carpet entrance that would make even Joan Rivers’s head spin.

Charter drag-party member Moskowitz, who also handles the less glamorous tasks of procuring port-o-johns and insurance for the event, says, "I look forward to the party every year to see the creativity the guests put into their themed outfits. My personal crowning achievement was my Tina Turner frock for the Divas party, complete with black eye and scratches (damn you, Ike)."

Ask any gender illusionist and she’ll tell you: Drag ain’t always cheap. While this writer has been the proud model of "dime-store drag" at numerous Fool’s Paradise parties in the past, many attendees put aside a considerable sum of money each season to make that perfect entrance on Labor Day. In several cases, entire residences of housemates show up en masse in matching outfits constructed by hired seamstresses and professional Broadway costumers.

"It’s funny how the cost starts. I used to spend $40 on a dress, $30 on a wig, and $10 on shoes and $20 on makeup," says the 13-year drag-party veteran Geovana Tuscadaro, one of the event’s producers and a key member of its design team. "Each of those costs jumps every year. The most I ever spent on a dress was $150. I’ve spent almost $100 on a wig but now I reuse wigs, so that $100 was an investment."


In addition to the drag on the guests, each year the host house is transformed from its larval-weathered wood exterior into a brightly colored butterfly via a taffeta cocoon. Even the fencing around the property gets a skirt. Tuscadaro explains: "To cover the perimeter, we buy about 150 yards of fabric every year. This covers the fence, the house, the entryway, the bar, and any little pieces of reality we want to pretend don’t exist for one fabulous afternoon."

Every drag queen needs a tiara for formal occasions, and for this event the house itself is no exception. "The real key to the decor is the roof decoration!" says Tuscadaro. The large constructed ornamentation has become a signature piece of each party, and Tuscadaro gladly credits one of New York’s leading industrial decor designers, who for the purposes of this event goes by the moniker "Marie Christmas."

"For years, I’ve partnered with a good friend who is an old-school visual queen on this party to make the ridiculous a reality," says Marie Christmas. "The first year I was involved with roof decor was 2003, for the ’Evil Queens and Fairy Princesses’ party, where I found myself 30 feet above the pool putting castle spires and battlements on the roof with my housemate Jay. You get used to heights."

The most sparkly roof tiara to date? "I’d say the most complex roof decor was the year the party had a Vegas theme," Marie Christmas replies. "We created the iconic ’Welcome to’ sign but changed the text to ’Welcome to Fabulous.’ The letters were cut on a CNC router, and we created depth by mounting the text on various stand-offs. The star on the sign was covered in paillettes, and the base was a dimensional box made out of foamcore. Amazing what a ton of industrial hot glue, seven colors of glitter, and some quality iridescent fabric can do for you!"

Sound involved and expensive? Well, it is. According to Christmas, "Most years the roof decor takes about one week of planning and buying, then one or two weekends of assembly between the both of us. Material costs range from about $300 to about $800, depending on the complexity of the design."

If the roof decor is the metaphorical tiara on the party space, the popular photo op can easily be considered the event’s "Jimmy Choos." As Marie Christmas explains, "The concept of the photo op basically evolved. It has always been about having an interactive moment for the girls, which makes the theme come alive." For the party theme "Housewives," there was a live bake sale benefiting the local "Ladies Auxiliary"; for "Working Girls," half of the event hosts dressed as flight attendants and created an actual working drink cart to serve cocktails, peanuts and hand wipes.

A background set piece was created for use as a photo op for the first time in 2009. At the "Dolls" party that year, a giant Barbie-esque packaging was constructed to allow party guests to become a doll.


As with any large affair held at a private home, if you don’t want the neighbors to complain, it’s usually a good idea to extend an invitation. For the drag party, this practice is not only good manners - it’s a necessity. Tuscadaro explains, "Since the power needs of the sound equipment usually is more than our house can handle on its own, the neighbors across the walk generously donate their electricity for the party."

When the party was moved to its current location in 2007, Tuscadaro, Moskowitz, Christmas and company were concerned about how the house’s owners would react. In a community filled with seasonal rentals and absentee landlords, this is rarely an issue; however, the house’s owners could hardly be considered absent. The live two doors down and are a straight couple to boot! Says Tuscadaro, "We knew we should ask them ahead of time, so we paid them a visit to get permission. We, um, might have left out the fact that it was a drag party and the guests would be hundreds of drunken drag queens spiking stiletto holes into their beautiful deck. We just said that we were going to be hosting a cocktail party for about 100 guests, which was roughly the size of the average party up until that year. Of course, 250 people showed up that year, including our landlords, who ended up thrilled to help us host the party." Tuscadaro continues, "Our landlord, Vinnie, offered to deck the pool the next year. He comes to the party every year and studies the crowd, and then makes suggestions for how the house can better support the crowd."


Although the party has grown to near epic proportions in its nearly two-decade history, the event hosts pay annual homage to its more modest beginnings. "We always have a drag dinner the night before that’s just our house and whomever stops by in drag, because they know we’re doing this," says Tuscadaro. "The idea is that you just grab a dress from last year that happens to be in the back of a closet somewhere. Occasionally the drag dinner is also my birthday dinner, so I have had to learn how to blow out candles without my wig catching fire."

The Fool’s Paradise Drag Party is held every year in Fire Island Pines on the Saturday before Labor Day. All in serious drag are welcome to attend. For directions, go to Fire Island Pines harbor, follow the "girls" with thick ankles and wrists, and when they reach their destination, you’re there.


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