You can always count on fabulous events every month in Key West. However, October definitely takes the cake with several action-packed layers of entertainment appealing to a wide variety of tastes.

Headdress Ball winner 2015 Key West

Daniel Bitnar created a lavish headdress to portray “Galactica, Ruler of the Universe,” and win the 2015 ball’s first prize. (Photo by Peter Arnow)

Our annual Fantasy Fest celebration, scheduled Oct. 20-29 this year, draws visitors from around the world. The event includes dozens of enticing parties, parades and street fairs ranging from family-friendly affairs to adult-themed soirees that can get a bit racy.

There are so many, in fact, that some people reach “sensory overload” before its grand finale.

One of the best official Fantasy Fest events, the Key West Headdress Ball, is celebrating its 35th year of dazzling audiences. It’s set for Thursday, Oct. 26, at the new Key West Amphitheater at Truman Waterfront Park, and more than 500 revelers are expected to attend.

The glamorous LGBT gala typically features about 25 contestants showcasing their original headdresses — some that tower high above their wearers.

The event is absolutely NOT your run-of-the-mill costume party, since it combines top-class entertainment and creative competition with incredibly elaborate costumes, masks and headdresses. These ensembles can take weeks to assemble, and I usually get updates from friends on their progress (and maybe a bit of gossip) while visiting our favorite poolside watering holes.

In past years some entrants have combined laser and LED lighting, fog machines and even intricate moving parts on their headdresses to leave the judges in awe — and come out “heads above” the rest.

One of my favorite volunteer jobs on the island is working as stage crew for the ball. I love experiencing first-hand all the behind-the-scenes work that goes into making such a remarkable production.

The VIP audience judges participants as they compete for cash prizes, including a first-place award of $3,000. Although most entrants are decked out from head to toe, participants are judged from the waist up only — focusing on their headdresses.

Gates open at 6:30 p.m., providing plenty of opportunities for spectators to meet headdress entrants and get that perfect selfie with them (of course!). Arriving early also allows everyone to mingle and grab a libation before the show begins to rev up.

As part of the Headdress Ball’s opening festivities this year, Key West Mayor Craig Cates will dedicate the new amphitheater.

Randy Roberts entertainer Key West

Renowned entertainer Randy Roberts will open the show at the 2017 Headdress Ball. (Photo by Peter Arnow)

The celebrity line-up includes the hilarious and talented Tom Luna as master of ceremonies; my favorite local radio host and DJ, Rude Girl, who will be working sound; and renowned entertainer Randy Roberts, who opens the 8 p.m. show.

Other local performers offer over-the-top entertainment between headdress presentations — and also cover any awkward pauses caused by a missing entrant or the dreaded wardrobe malfunction.

The Key West Business Guild, one of the oldest LGBT business organizations in the U.S., has produced the ball since it began. The event is a major annual fundraiser for this worthy organization, which has been welcoming LGBT visitors to our little slice of paradise since 1978.

General admission tickets are $30 per person, with reserved tables for four people starting at $250. To purchase tickets, visit

If you’re arriving early for Fantasy Fest, please be sure to check our brand-new gay event for 2017, the Key West Bear Weekend — growling its way onto the island with lots of “bearriffic” activities planned for Oct. 19-23 (woof!).

One more thing: please note that some visitors book Fantasy Fest accommodations a year in advance, so make your reservations NOW if you hope to attend. I’ll see you during the festival!