Fantasy Fest 2026 runs Oct. 16 through 25 under the theme "Musical Icons and Iconic Musicals." Duval Street and the Caroline Street bars get most of the coverage. For a household between Flagler Avenue and Kennedy Drive, the dates worth marking fall elsewhere. A registration deadline lands four days before the festival opens. Judging happens on a Monday evening. There is a pet show on a Wednesday. The festival's last full afternoon goes to Bayview Park.
The Bayview date carries a second piece of news. The city opens bids for the park's next renovation phase on Oct. 26, the day after Children's Day. So the neighborhood's biggest Fantasy Fest afternoon also comes just before the paperwork for Bayview's next phase gets underway.
The resident's calendar, in order
| Date | What | Where |
|---|---|---|
| Mon., Oct. 12 | Fantasy Façade registration closes | Your own front porch |
| Mon., Oct. 19 | Fantasy Façade judging | Island-wide |
| Wed., Oct. 21 | Pet Masquerade | Coffee Butler Amphitheater, Truman Waterfront |
| Fri., Oct. 23 | Captain Morgan Masquerade March, the "Locals' Parade" | Old Town |
| Sun., Oct. 25 | Children's Day, noon to 5 p.m. | Bayview Park |
| Mon., Oct. 26 | Bids open on Bayview Park Renovations Phase 2 | Office of the City Clerk, 1300 White St. |
The order matters for anyone planning around it. Two of these dates come before the parade weekend and one comes after the festival ends. A Midtown household can take part in Fantasy Fest from start to finish without going to the Street Fair once.
The porch is the first entry
The Fantasy Façade contest is open to "guesthouses, businesses, and homes across the island." That means a ranch house on a quiet Midtown street can compete alongside a Duval Street guesthouse. The contest is presented with Sloan's Haunted Key West, and every entry goes on the official Fantasy Fest app map. That map is how people find decorated houses when they drive around town looking for them. Judges score on creativity, how well the entry represents the theme, and what the organizers call the "WOW Factor."
The categories favor some kinds of homes over others:
- Spooktacular Showstopper, best overall façade: $1,000
- Home Takes Center Stage, best residential take on the theme: $500
- Business Takes Center Stage, best commercial take on the theme: $250
- The Great Pumpkin, best traditional Halloween theme: $250
- Stagecraft, most creative design: $200
- Monster Mash, scariest display: $100
- In the Spotlight, best use of lighting: $100
- Encore, most entertaining with sound or movement: $100
The residential prize pays twice what the business prize pays. A home that leans into this year's musical theme has a category of its own with real money behind it. A household that would rather do witches and jack-o'-lanterns has The Great Pumpkin. Midtown's mid-century houses tend to sit back from the street on deeper lots than Old Town cottages. That leaves room in the yard for the lighting and movement that the In the Spotlight and Encore awards are judged on.
The entry form went live Sept. 1, and the deadline is Oct. 12. Judging is set for Monday, Oct. 19, so a display needs to be finished and lit by the middle of festival week, before the parade weekend. Fantasy Fest's own schedule says dates are "subject to change," so check the official page before setting anything up.
Wednesday belongs to the dogs
Two days after judging, the Pet Masquerade takes over the Coffee Butler Amphitheater at Truman Waterfront on Wednesday, Oct. 21. Florida Keys Media presents it. Entry is $25, registration opens at 5 p.m., and the show starts at 6:30. The 90 minutes between registration and showtime are enough to get there after work, check in and get a costume back on a dog that has already shaken half of it off.
The categories include Junior, Pet/Owner Lookalike, Most Exotic and Best Theme Adaptation, plus an Overall Winner and Best in Show. Watching is free. Registration fees go to the Monroe County Sheriff's Office Animal Farm. For a household whose kids already have costumes picked out for Sunday, the Pet/Owner Lookalike category is a cheap trial run on a weeknight.
As Keys Weekly puts it, "Costume up with your favorite critter friends at this over-the-top competition or cheer them on from the audience."
Friday's parade carries the locals' name
The Captain Morgan Masquerade March, which Fantasy Fest itself nicknames the "Local's Parade," steps off Friday, Oct. 23. Costumed marchers move through Old Town, stop at selected guest houses along the route for adult beverage samples, and end at the mile-long Fantasy Fest Street Fair. Paparazzi Row is set up beforehand with dance music, local photographers, photo booths and selfie stations. This is the one resident-branded event of the week that takes place in Old Town. The Deep Eddy Vodka Fantasy Fest Parade follows on Saturday, Oct. 24. It has been an island tradition since 1979.
Sunday comes back to Bayview Park
On Sunday, Oct. 25, the last full day of the festival, Children's Day fills Bayview Park from noon to 5 p.m. The lineup includes games, food, rides, entertainment, arts and crafts, and a costume contest for kids. The City of Key West has a property event notice on file reserving Bayview Park for the event, with setup starting Saturday, Oct. 24. Expect equipment arriving at the park the day before, while the Saturday parade is still happening downtown. The festival's last official event takes place the same afternoon, "The Fat Lady Sings" Tea Dance at La Te Da on Duval Street.
The city confirms Children's Day at Bayview this year even though the park is mid-renovation. On Sept. 24, 2026, the city updated its invitation to bid for "ITB 26-017 Bayview Park Renovations Phase 2 Project." Bids open Monday, Oct. 26, at 3 p.m. in the Office of the City Clerk at 1300 White St. The bid package covers demolishing existing structures and building a new multipurpose park-support building, along with utilities, concrete slabs, sidewalks and a basketball court.
Here is what that timing does and does not tell a Midtown family. Opening bids is the first step. As of the end of September, no contractor has been named and no start or completion dates for Phase 2 have been published. The available public notices also don't say which parts of the park, if any, are fenced off right now. Children's Day goes ahead at Bayview this year. What the park looks like for the 2027 edition depends on bids that open the next afternoon. The 2027 Fantasy Fest theme will be announced the same day.
Getting there on Flagler
Midtown households will cover some of this week's trips on Flagler Avenue, which is under construction. The city is rehabilitating Flagler between White Street and Reynolds Street. The work includes ADA-compliant curb ramps, new sidewalk sections, milling and repaving, and new pavement markings. "No parking" signs are posted in the work zones, access to all homes and businesses stays open, and the work is expected to continue through the end of the year. So the stretch most likely to have a no-parking sign during festival week is the closest one to the Old Town end of the parade route.
Farther east, the signal at Flagler Avenue and Fifth Street was one of the first locations finished, on June 11, in a five-year city and Keys Energy program to upgrade more than 30 traffic signals. That intersection is already done, so it won't be adding to festival-week delays on the Midtown side.
For a front porch going up for the Oct. 12 deadline, or a family weighing what Bayview's next phase could mean for their corner of Midtown, The Spottswood Team keeps an eye on the city's park and street projects and is always glad to talk them through with neighbors. Get in Touch.
