The Wigstory

Let’s get one thing straight right from the start: if you think that Cherry Grove is the only community in Fire Island that embraces drag, you’re dead wrong. Not only do many of the Invading Queens on July 4th live in the Pines, but the community is also home to the legendary, record setting annual Labor Day Drag Party. This is its glitter-soaked, sequin covered, glamor story, an event where rhinestones rule, inhibitions vanish, and Madonna impersonations have (literally) made history.

Once Upon a Lipstick-Stained Time

It all began quietly in 1996, like many great revolutions do: over dinner. Michael Green, David Steffen and their housemates at 480 Tarpon Walk—cheekily dubbed Chateaux Helleaux for the summer—hosted a dinner where the only requirement was that guests come in drag. None of the attendees were “professionals”. In fact, many of them were new to drag. But when your Pines dinner invitation says “Drag Required” you lay hands on the finest couture you can fit into, tease up a wig into Soap Opera status and slide into your high altitude ankle breakers. Because you know the Pines queens do nothing halfway.

The dinner was a hit and word quickly spread that something fabulous had started. The following year friends began dropping by post-dinner in drag just to bask in the glittery afterglow.

It quickly dawned on Michael and his housemates that this needed to be more than just a dinner. The following year they turned it into a full-blown cocktail party. Come one, come all! Come in drag or don’t come at all!

And girl, did they come! With high hair and higher heels, dressed in everything from leather to lame, the Pines boys sashayed their way into a new tradition, the annual Labor Day Fire Island Drag Party.

Drag for the People, By the People

What made the Fire Island Drag Party unique is it flipped the script on traditional drag events. Instead of having drag queens performing on a stage, the boys created a party where everyone dressed up, everyone participated. There was no audience and no VIPs— just a tidal wave of wigs, heels, dresses and good times. Drag at this party wasn’t about performing, it was about being.

Another feature: The price of admission was wearing at least three pieces of drag. As Chris DeCarlo, one of the spiritual mothers of the party put it: “Admission is free. Drag is mandatory.”

For many people the party was their first experience in drag. And while there were a few wobbles as the newbies found their drag legs, the freedom and fun of it all was intoxicating.

Inevitably, there were people who came to the party out of drag pleading to get in, stating they weren’t dressed because they didn’t know about the party beforehand. The Door Queen was always firm, “No drag, no entry”, but would assure them that if they went back to their house they would almost certainly find something they could wear. And more often than not, they returned half an hour later suitably attired.

It’s worth noting, the Fire Island Drag Party took root before Drag Race made tucking and contouring part of the mainstream. Indeed, in the early days, being “the drag house” was hush-hush.

“A friend later told me that his housemates had referred to us as ‘the drag house’ with a raised eyebrow,” Chris DeCarlo recalls. “As if we were doing human sacrifices.”

But the party pushed against the norm and the Pines community responded. Attendees crossed every genre, from muscle boys to theatre queens, from the very young to those on social security.

As one party goer noted “The muscle boys in my house went from ‘I’m never doing drag!’ to ‘I need a boa!’ in 30 seconds! It was infectious and everyone had a good time!”

Over the years the party ping-ponged across a few houses before finding its spiritual home at 495 Tarpon, now christened Fool’s Paradise. Themes emerged and the décor became more extravagant. Think a Moulin Rouge windmill on the roof, the “Welcome to Fabulous” sign the year the theme was “Vegas” (which now hangs over the dining table in the house) and the fierce custom couture rooftop mannequins that were lit by spotlight the year of the Black and White Ball.

Putting all this together was no easy task. The disco balls had to be hung, the deck had to be painted, the fabric had to be stapled, the bar had to be stocked, and the DJ booth and speakers had to be setup because good sound was essential. As Dolly Parton once said, “It takes some effort to look like this!”

However, the shared labor of love by the dozens of party hosts, who shrugged off beach time and Tea time to get the house ready, produced a level of decor that made the Met Gala look like a yard sale. And people noticed. Passersby began to gather outside to see who was coming and going, take photos and get a glimpse at the party inside. This reached a high point when the party relocated to Scaup Walk, a move that turned it from a private secret into a public spectacle. Drag on display! People getting off the ferry would see the party decor from the harbor and feel the excitement - something fabulous was happening.

Not surprisingly, the Drag Party became one of the major events of the summer. Being the Pines, the outfits at the party were always nothing less than fabulous. Many were brand new, but there was also a lot of vintage, accessorized to the hilt. Some housemates dressed in matching themes, but many twirled up their individual looks to make a statement. From bashful beige suits and conservative pumps to flamboyant fuchsia gowns and bejeweled high heels, it helped set a tone of fierce, friendly and fabulous. Everyone was happy to be there and excited to see each other. Air kisses were exchanged, cocktails sipped through straws, and the dance floor was packed as the amazingly talented DJs spun the summer’s hits.

One particularly memorable party happened in 2007. The theme was Working Girls and the Tarpon housemates arrived dressed as matching airline stewardesses, complete with a real working airline bar cart (which quickly became a satellite bar for the party!). Then mid-party, the group got together and did a full safety demo and then jumped into the pool in inflated life vests. Dragged-out aviation fantasy!

By 2009 it became clear to the organizers this was no longer their party. It belonged to the community. Attendance had grown tremendously, and most party goers were people they barely knew. They heard stories about the extensive preparations various houses went through, including Dress Parties and Pre-Party Runway Shows (with Step and Repeat of course). In one house the entire day was devoted to the party with one attendee famously admonishing his housemates, “No beach on drag day!”

As Chris DeCarlo noted, “It seemed everyone had their own rituals. This was their party. We were just hosts.”

Love Is In The Air

One of the often unspoken features of drag is how frisky it could be.

“Being in drag in the Pines gives you an incredible feeling of freedom and power, way more so than you would have otherwise” noted one long time party goer, “You have no problem going up and talking to anyone about absolutely anything.”

The party freed the boys from convention. In short skirts, high heels and often no underwear, it allowed them to let their freak flags fly -- at the party and after.

Said a former Pines resident, “Our first three-way happened when a guy hit on me and my husband dancing at Tea after the drag party! Who would have guessed?”

Breaking Records

It was at the planning meeting in 2014 that Chris DeCarlo unveiled a big, Blonde Ambition:

“We are going to set the Guinness World Record for the Largest Gathering of People Dressed as Madonna.”

The team agreed and planning for “It’s a Madge, Madge, Madge, Madge World” got underway!

It was a huge challenge, but the Pines is a place where they did a nighttime beach party back in the 70s when they said it couldn’t be done.

But a Guinness World Record?

No problem! Because in the Pines we didn’t get to where we are by accepting limits!

And on the day of the party, Madonna’s began appearing everywhere, from Sail Walk to the Meatrack, and Ocean to Bay. The Queens were on the move and something big was going to happen.

“Holiday Madonna”, “Vogue Madonna”, “Like a Virgin Madonna”, “Sex Book Madonna” and every other incarnation was there. In the Pines that day it was a Madge Madge Madge Madge World!

And they kept on coming!

Until a record was created!

With 440 guests dressed as Madonna it was deemed the largest gathering of people dressed as Madonna and awarded a Guinness World Record.

The Guinness judge? A straight guy who shamelessly flirted his way through the sea of lace, leather, and cone bras, then hoisted the certificate triumphantly in the air as if to say “Yass, Queens!”

And so HISTORY was made!

A Legacy That Slays

Today, the party is hosted by Ryan Chavez and Paul Zeman at their home on Midway. Recent themes have included “Jubilee” – a royal spectacle with Elizabethan realness, and Pink Lotus, replete with Valentinas and a floating Jennifer Coolidge doll. Admission is still free. Drag is still non-negotiable. And the magic? Very much present. Nowhere else can a 21-year-old first-timer in six inch heels meet an 80-year-old in vintage Halston on the dance floor and celebrate life and the fun and fantasy of it all.