Key West · October

Fantasy Fest

October 16 to 25, 2026 Key West, Florida

Fantasy Fest is Key West's biggest party, a 10-day costuming and parade celebration that takes over the island every October. It started in 1979 when a handful of locals decided the slow season needed a shot in the arm. It now pulls tens of thousands of visitors to Duval Street for parades, masquerade balls, body paint and street fairs.

The 2026 festival runs October 16 through 25, and the theme is Musical Icons and Iconic Musicals. Expect plenty of Bowie, plenty of Gaga, and more than one Phantom of the Opera mask working its way down Duval.

Quick Facts

Dates: October 16 to 25, 2026
Theme: Musical Icons and Iconic Musicals
Parade: Saturday, October 24 at 7 p.m. on Duval Street
Where: Old Town Key West, centered on Duval Street
Cost: Street events are free; balls and parties are ticketed
Crowd: Up to 75,000 visitors over the ten days

What Fantasy Fest actually is

Think Mardi Gras with more sunscreen. For ten days the island fills with costume contests, themed parties, drag shows, a pet parade and two big street fairs. Some events are polished, some are gloriously weird, and most of the crowd treats the sidewalk as a runway.

The festival peaks on the final Saturday with the Fantasy Fest Parade, when lighted floats and marching groups roll up Duval Street in front of the biggest crowd of the year. If you only make one event, make it that one.

The big events on the 2026 calendar

The full schedule lands closer to October, but the anchor events barely move from year to year:

· Royal Coronation: Key West crowns its Fantasy Fest King and Queen after a months long fundraising race that benefits local nonprofits
· Goombay Festival: a two night Bahamian street party in Bahama Village with island food, junkanoo music and dancing, held the first weekend
· Headdress Ball: the most over the top ticketed party of the week, judged on exactly what the name says
· Captain Morgan Masquerade March: the locals parade, a costumed walk from the Key West Cemetery down to Duval on the final Friday
· Pet Masquerade: dogs, cats and the occasional iguana in costume, always a family favorite
· Fantasy Fest Parade: Saturday, October 24 at 7 p.m., the main event

First timer tips

A few things locals wish every visitor knew before festival week:

· Book your room now. Old Town hotels sell out months ahead and rates climb fast in October.
· Body paint alone does not count as clothing under city rules. Key West police publish costume guidelines every year; read them before you commit to an outfit.
· Bring cash for the street fairs and tip your bartenders. Lines move faster for people who do both.
· Traveling with kids? Aim for Goombay, the Pet Masquerade and daytime events early in the week. Upper Duval after dark is an adults-only scene.
· Pace yourself. It is ten days, not one.

Getting there and getting around

Fly into Key West International or drive the Overseas Highway, about three and a half hours from Miami without traffic. Once you are on the island, park the car and leave it parked. Old Town is walkable, the free Duval Loop bus runs during festival week, and bikes rent everywhere. Parking near Duval during the parade is close to impossible, so do not plan around finding it.

Want more on Fantasy Fest?

Official details from the organizers, plus Keys Weekly's coverage from the newspaper.

fantasyfest.com Keys Weekly Coverage

On the Calendar Now

Upcoming Fantasy Fest listings from the Keys Weekly events calendar.

Fri, Oct 16 · All Day

Fantasy Fest 2026: Key West's Wildest Ten Days

Key West

Frequently Asked Questions

When is Fantasy Fest 2026?

October 16 to 25, 2026, in Key West. The Fantasy Fest Parade is Saturday, October 24 at 7 p.m. on Duval Street.

What is the Fantasy Fest 2026 theme?

Musical Icons and Iconic Musicals. Costumes built around musicians, bands and Broadway are the ticket this year, though nobody checks your homework.

How much does Fantasy Fest cost?

Watching the parade and walking the street fairs is free. Signature ticketed parties like the Headdress Ball and Coronation typically run from around $40 to $150 and up depending on the event.

Is Fantasy Fest family friendly?

Parts of it. Goombay, the Pet Masquerade and daytime events work for kids. The late night scene on Duval is for adults, and costumes get more adult as the week goes on.

Where should I park for the parade?

Ideally nowhere near it. Stay in Old Town and walk, or use the city garages and the free Duval Loop bus. Traffic around the parade route locks up hours before the 7 p.m. start.

More Annual Events in the Keys