Editor’s Note: T-minus 40 days until the 2026 Fantasy Fest parade. Join the Keys Weekly each week for exclusive Fantasy Fest features highlighting the people and projects behind the island’s biggest annual party.
Fantasy Fest is an endless showcase of local creativity — a weeklong parade of themed group costumes, extravagant floats, wild makeup and storefront decor galore. What may go unnoticed is the individual imagination that happens behind the scenes. One of the most notable examples of this quiet creativity is the process by which each year’s theme is selected.
In the early days of Fantasy Fest, themes were selected by event founders Bill Conkle, Tony Falcone, Joe Liszka and Frank Romano. Early themes included “House of Horrors” (1980), “Va Va Voom” (1981), and the original, “Old Key West” (1979). The idea was to come up with concepts that would grab the attention of out-of-town guests, in hopes of bringing tourism dollars to the community during the slow hurricane season. History has proven that it worked, perhaps better than anticipated, as the festival grew from a single weekend to a10-day spectacle.
As the party expanded, festival organizers began outsourcing each year’s naming rights to the general public, particularly locals who participate in and enjoy the festivities year after year.
Each summer, a public “Name the Theme” contest is announced, with entries submitted to festival director, Nadene Grossman Orr, or via the Fantasy Fest website and social media channels by Sept. 1. Submissions are reviewed by judges, including Tourist Development Association board members, who select the idea that best encapsulates Key West’s creative spirit, or as the contest phrasing states, based on what “sparkles with exciting possibilities.” Past winning themes include “Pirates, Pundits and Political Party Animals” (2008), “Super Heroes, Villains & Beyond” (2013), and “In Tune, but Off Key: Celebrating 40 Years of Fantasy” (2019).
This year, the winning entry came from wine connoisseur and fun-starter, Stephanie Southgate. “Musical Icons and Iconic Musicals” earned Southgate VIP tickets to watch the parade from the grandstand and, more importantly, bragging rights. For Southgate, a nearly 30-year Key West resident, the theme seemed past due.
“I’m not typically a super creative person, but have often thought, ‘What would I want the theme to be?’ Then, it just came to me — how have we missed music and musicals?’”
Unaware of the annual theme contest, she reached out to Grossman Orr with the concept, which was cemented in her mind after watching “Hamilton” and recalling an extravagant Broadway-themed Fantasy Fest parade float from a few years ago. Southgate was directed to enter her idea in the contest and was subsequently chosen to guide the creative juices of the 2026 festivities.
As a regular attendee since 1998, Southgate is honored, but also recognizes some pressure to step up her participation.
“Some years you’re so invested, others not as much. This year, I have so many friends coming in from out of town to celebrate, I’ve already planned countless costumes.”
