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Mr. Halloween: Irreverent, illegal, inspiring

Glenn Terry, Miami Herald 22 October 2008

Coconut Grove's Mr. Halloween, Gregg Gillingham, passed away two weeks ago, at the age of 61, in Montevideo, Uruguay.

It was fitting that he should go during our spookiest month. Many of his Octobers were spent preparing for incredible Halloween celebrations. Behind Gregg's quiet, unassuming facade was one of the world's great party animals. With twinkling eyes and a smile shrouded by a huge mustache, he created All Hallows Eve gatherings that became legendary.

They started in the 1970s with a few dozen attendees, then, heading into the 1980s, his "guest list" (anyone could come) grew into the thousands. Gregg's house was the only place to be on Halloween night.His parties were so over the top. Imagine your average house with bands playing in the front yard, back yard, and on the roof. His gatherings had that and my, were they LOUD.

I remember leaving one year, unlocking my car parked a block and a half away. The band still sounded as loud as when I was standing next to it. There were pigs roasting over flaming pits. The bars served beer, wine and moonshine.

Gregg was such a mischievous lad, happiest when he was teetering on the edge of the law. Friends would gather weeks before October 31 to build the party's frightening, enlightening -- and erotic -- sculptures. That's how it was and the whole world was invited.

Of course, the costumed people attending were great too, packed into the Gillingham Estate like sardines. Some even came as sardines. His guests were so creative, not the "how naked can you get" variety often found in Key West.

Gregg's Halloween parties weren't appreciated by some neighbors. For them, it was like you were there even though you weren't. Surely some had small children. This didn't seem to affect Gregg, as he extended invitations to all. Finally, a neighbor took him to court. A week later, a judge was telling Gregg, "`If you do this again I will have you locked up."

Like the perpetual 15-year-old that he was, he could not imagine being encumbered by a regular job, marriage, fatherhood or a jail cell. He chose a new venue for his infamous parties. He then began producing his Halloween events on a large scale in places like Virginia Key and the Deering Estate. The commercial affairs were fairly successful, but not as intimate, illegal or as fun as the home version.

After a few years, Gregg canned the whole idea, saying, "I think its time to enjoy other people's parties." He told me about one he attended in Orlando where he won the "`best costume award." He had been a giant gecko standing on stilts. Gregg brought out the impressive Styrofoam lizard head he had worn. Its eyes were lit bright with motorcycle headlights. The last day of October was Christmas to him.

Gregg grew up in South Miami and quickly gravitated towards the Grove. It fit his party hearty personality. He spent most of his life playing, but when he worked it was in the construction business. His white pickup was always stuffed with tools and his back yard strewn with cool junk.

Mr. Halloween once bought an eight-unit apartment complex near 27th Avenue. He figured it would make more money as a motel but the zoning laws did not allow it.

There was an exception for Bed & Breakfast establishments, but Gregg didn't like to cook. Gregg being Gregg, he opened the Grove's first Bed and No Breakfast. His hand-lettered sign out front made me laugh, but when he sold it a few years later the property made him enough money to retire.

In the 1990s he switched from party host to world adventurer. He sailed his boat to Maine single-handed. Next, he toured North Africa on a motorcycle. Gregg explored the South Pacific a few years ago. He told me about living on $5 a day, encamped on a remote island.

He'd always return, though, to his Grove home on Tigertail Avenue, often with a new girlfriend in tow.

The Greggster discovered airplanes a few years ago and decided to fly around the world. He bought an old single-engine Mooney and began installing extra gas tanks in its wings. You need lots of gas to cross the Atlantic. He lacked a companion but not for long. Three years ago he found the love of his life in a Miami River boatyard.

Rebecca Bartlett was preparing her sailboat for her next adventure. Soon they were planning a lifetime of flying and sailing together. Rebecca and Gregg took off for South America, their first stop, in December 2006. They tossed out their schedule when they realized was how much fun they were having along the way.

Almost a year ago I got a newsletter from them sent from Montevideo, Uruguay, (www.cheekymooney.com). Apparently they had fallen in love with the sleepy, colonial city on the Rio Plata. But Gregg's heart condition probably got the best of him. Rebecca informed their friends of Gregg's passing in an eloquent letter. There will be some sort of memorial celebration, but no date is set. "It's got to be bawdy, irreverent and maybe even illegal," said one of his buddies.

His longtime friend, Bobby Deresz, suggests putting his ashes in a Jack-o-lantern for a ride in the King Mango Strut. Whatever it is will surely end with a heckuva party, a fitting tribute to Mr. Halloween.

Glenn Terry is an educator, attorney and activist who lives in Coconut Grove.