Fantasy Fest 2026 in Old Town Runs on a Closure Calendar

Fantasy Fest 2026 runs October 16 through 25 under the theme "Musical Icons and Iconic Musicals." That is ten days. For anyone who lives in Old Town, the parts that actually change how a street works come down to six days, and each of them has a posted start time. On the other days the festival mostly happens away from Duval, at Petronia and Emma, Truman Waterfront Park, Bayview Park and the porches of houses entered in a decorating contest.

This year is different in one practical way. It is the first Fantasy Fest since the city's free Duval Loop shuttle was suspended. The Loop was what used to connect those spots. Without it, getting around is the hard part of the week.

The Six Days That Change the Streets

The City of Key West posts its festival street closures on its online calendar, and the official Fantasy Fest schedule fills in the event times. Here are the six days in order:

1. Friday, October 16, and Saturday, October 17. The city lists Petronia Street from Duval to Emma as closed both days for Goombay.
2. Monday, October 19. The Fantasy Fest 5K and 1-mile walk brings a rolling closure. The 200 block of Duval closes from 4 p.m. for setup and stays closed until breakdown ends at 8:30 p.m.
3. Tuesday, October 20. Applerouth Lane closes at 5 p.m. for the Tutu Pre-Party Parade. Rolling closures start at 6 p.m. on a route from Mary Ellen's along Duval, Angela, Greene and Whitehead to General Horseplay on Caroline.
4. Friday, October 23. The Captain Morgan Masquerade March forms in the residential blocks east of Duval. Paparazzi Row starts at 4 p.m. at Fleming and White. Marchers line up at 5 p.m. at Frances and Petronia, step off at 5:30 p.m. and end at the Duval Street Fair.
5. Saturday, October 24. Duval Street closes at 6 p.m. for the 7 p.m. parade, and the city's notice runs the event until 10 p.m.

The Friday march is the one most likely to catch Old Town off guard. It starts on streets with houses, not bars. Fleming and White, and Frances and Petronia, will be crowded in the late afternoon, and the march only reaches Duval afterward. The city closure notices covered in this post do not include a block-by-block closure list for the march or the Duval Street Fair, so plan to drive around that part of the neighborhood on Friday afternoon.

Saturday's route is posted in full. In the city's words:

"The parade begins at Truman Waterfront Park/Southard Street, left on Whitehead Street, right on Front Street, right on Duval, right on United, right on Whitehead back to Truman Waterfront Park. Expect traffic delays."

The route makes a full loop, starting and ending at Truman Waterfront. Whitehead is used twice, heading out and coming back. For anyone living near Southard and Whitehead, the parade starts and finishes nearby.

The Rest of the Week Happens Off Duval

The closure list shows where the festival takes over streets. The all-ages events are spread around the outer parts of the neighborhood.

Goombay is the event listed above that sits most inside a residential area. The festival lists it as free and family-friendly, with its main stage at Petronia and Emma in Bahama Village. The two sources give different end times. The festival schedule says noon to midnight, and the city's closure calendar says noon to 11 p.m. If the timing matters for your block, plan around midnight.

The Pet Masquerade and Children's Day are at opposite ends of the week and opposite sides of Old Town. One is at the waterfront on Wednesday evening. The other is at Bayview Park on the last Sunday afternoon, the day after the parade. The 2026 schedule describes Children's Day with food, rides, games, arts and crafts, and a children's costume contest.

The 12-foot illuminated pyramid at Opal Key and the mandala outside the Mel Fisher Maritime Museum are both close to the parade route's turn onto Front Street. They are on display all week, so you can see them on a quiet weekday without waiting for parade night.

The city calendar also lists two ticketed events at Coffee Butler Amphitheater. The SPCA Royal Coronation opens the festival on Friday, October 16, from 6 to 9 p.m., under a City Commission resolution passed in May. The Headdress Ball is Thursday, October 22, with doors at 6:30 p.m. and the event running from 8 to 11 p.m.

Porches Are Judged on October 19

One festival event takes place entirely on residential streets. The Fantasy Facade contest, sponsored by Sloan's Haunted Key West, is open to Key West residents and businesses. Entrants decorate their homes or storefronts around the festival theme or Halloween. The grand prize is $1,000 for the best "Spooktacular Showstopper," and more categories are listed on the festival's Fantasy Facade page.

Registration closes Monday, October 12, and judging is Monday, October 19. That is the same evening the 5K closes the 200 block of Duval, so the judging and the first weeknight closure happen together. Entries are marked on the Fantasy Fest app map. For anyone who wants to walk the residential blocks and see the decorated houses, that map is the guide.

The facades connect the theme to the neighborhood more directly than anything else on the schedule. They stay up for the whole festival, on side streets that never close.

The First Festival Without the Duval Loop

With events spread from Bayview Park to Truman Waterfront to Front Street, this would normally be the Duval Loop's busiest week. This year it isn't running.

KONK Life reported on October 3 that the Loop has been "suspended" since December 31, 2025, and got no funding in the city budget year that began October 1. According to the same report, the city's finance director has asked the Monroe County Attorney's Office for a written opinion on whether Tourist Development Council money could cover some or all of the Loop's operating costs. KONK Life also reports that a new service called the Island Hopper will replace Key West Rides on-demand and Workforce Express "in the coming months." None of that will be in place by October 16.

The festival's parking and transportation page covers the other options:

• Rideshare and taxis. Drivers are asked to stay at or east of Simonton Street, so riders need to walk toward Simonton to get picked up or dropped off.
• Old Town Garage, 301 Grinnell Street. The garage has about 300 spaces at Caroline and Grinnell, at $6 an hour or $48 a day, and special event rates may apply. A residential permit covers up to four hours of free parking once per day.
• Other public lots. Mallory Square charges $7 an hour, Key West Bight $6 an hour, and Truman Waterfront on Southard $6 an hour, with special event rates possible at Truman.

The same page says resident-only street markings are enforced. Its embedded parking map is labeled 2025, so check the city calendar for any updates for this year.

The garage is open 24 hours, but the permit's free window is four hours once a day. That window covers a single evening event. The Masquerade March runs from a 4 p.m. start to a Duval finish, and the parade from 7 to 10 p.m. Goombay's noon-to-late days and the full parade night, starting with the 6 p.m. Duval closure, run longer, and any time past the free four hours is charged at the garage's posted rates. The other options are walking, biking or a Simonton Street pickup.

What Hasn't Changed

No new festival-wide rules for noise, alcohol or residential parking showed up in the 2026 notices covered here. The city's standing special-events process still applies. Any event expected to go over a location's decibel limit needs City Commission approval, and the same location cannot get another exemption within 60 days. The festival's code of conduct, including its rules for public property and areas outside the festival's designated zone, is posted in the Fantasy Fest FAQ.

The organizers say the 2026 schedule is subject to change as event partners update their details. The city calendar is the place to check street closures, and the festival app is the place to check event times and facade locations.

Our team at Bascom Grooms Real Estate has worked out of Key West since 1999, and Fantasy Fest is part of every October we've spent on the island. Whether you're working around Friday's march or wondering what parade week looks like on your block, we're glad to talk it through. Contact Us.

This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.