The 2026 Fantasy Fest parade on Saturday, Oct. 24, starts at Truman Waterfront Park and Southard Street. It runs out along Whitehead, Front, Duval and United, then turns back up Whitehead and finishes at Truman Waterfront Park, where it began. Most Key West neighborhoods see the parade go by once. Truman Annex is at both ends of the route.
That pattern holds after October too. Between now and late January, nearly every date on the Annex's calendar falls within a short walk of its gates. Many events repeat on a monthly schedule, and several of the best ones are free. The season starts with the biggest night of the year at the Annex's edge. Then it gets smaller and more regular, and it stays close.
Parade night, from the starting line
The City of Key West's special events calendar lists the full route and timing. Duval Street closes at 6 p.m., the parade starts at 7, and the city's notice runs the event until 10 p.m. with a plain warning to expect traffic delays.
The route, in order:
- Start at Truman Waterfront Park and Southard Street
- Left on Whitehead Street
- Right on Front Street
- Right on Duval Street
- Right on United Street
- Right on Whitehead Street, back to Truman Waterfront Park
The parade travels Whitehead twice, once heading out and once coming back. That makes Whitehead the street around the Annex most likely to be busy at both the start and the finish. The city's notice gives no separate closure times for Southard, Whitehead or Fort, and it says nothing about parking at the waterfront park. The safest plan is to expect delays at both ends of the route from early evening until the last float is back.
The two nights before, on East Quay Road
Parade night is the third night in a row of Fantasy Fest activity at the waterfront. Coffee Butler Amphitheater, at 21 East Quay Road inside Truman Waterfront Park, hosts the Pet Masquerade on Wednesday, Oct. 21, from 5 to 9 p.m.
The next night, Thursday, Oct. 22, is the Key West Headdress Ball. The city's notice says setup starts at 8 a.m., doors open at 6:30 p.m. and the event runs from 8 to 11. The official Fantasy Fest schedule calls this the 43rd Headdress Ball, with Randy Roberts hosting and WEOW's RudeGirl playing music.
That 8 a.m. setup time matters for anyone who lives close to the amphitheater. Work on the Headdress Ball starts about 12 hours before the doors open, on the same day as the Thursday farmers market a short walk away. The market's organizer lists the new 2026 hours as 1 to 6 p.m., every Thursday of the year except Thanksgiving, with free parking for residents who have the sticker. On Oct. 22, the produce stands and the ball setup share the waterfront for most of the afternoon.
The season at a glance
After parade weekend, the Annex's calendar moves to a lower volume. These are the confirmed dates within walking distance, from now through January.
| Date | Event | Where |
|---|---|---|
| Thu., Oct. 15 | Little White House Foundation members live-stream gathering featuring Sheila C. Bair | Little White House Foundation |
| Sat.–Sun., Oct. 17–18 | Living History weekend, 10 a.m.–2 p.m. | Fort Zachary Taylor |
| Wed., Oct. 21 | Pet Masquerade, 5–9 p.m. | Coffee Butler Amphitheater |
| Thu., Oct. 22 | 43rd Headdress Ball, doors 6:30 p.m. | Coffee Butler Amphitheater |
| Sat., Oct. 24 | Fantasy Fest parade, 7 p.m. | Starts and ends at Truman Waterfront Park |
| Sat.–Sun., Nov. 21–22 | Living History weekend, 10 a.m.–2 p.m. | Fort Zachary Taylor |
| Wed., Nov. 25 | Harbor Walk of Lights kickoff, music at 5 p.m. | Greene and Elizabeth Street plaza |
| Thu., Dec. 3 | Pet Pictures with Santa | Historic Seaport |
| Sat., Dec. 5 | Hometown Holiday Parade | City route |
| Sat., Dec. 12 | 35th Lighted Boat Parade | Along the Harbor Walk |
| Sat., Dec. 19 | Great Gingerbread Build, free, 11 a.m.–2 p.m. | Little White House |
| Sat.–Sun., Dec. 19–20 | Living History weekend, 10 a.m.–2 p.m. | Fort Zachary Taylor |
| Sun., Dec. 20 | Holiday Classic Car Show and toy drive, free | Conch Republic Seafood Company lot, Harbor Walk at Greene |
| Tue.–Wed., Dec. 22–23 | Holiday tours and card presentations | Little White House |
| Wed., Jan. 20 | Yacht Rock Revue, show at 7:30 p.m. | Coffee Butler Amphitheater |
| Tue.–Wed., Jan. 27–28 | Truman Literary Series and Truman Art Series | Little White House |
Third weekends at the Fort
The steadiest thing on that list happens at Fort Zachary Taylor. Florida State Parks schedules Living History weekends on the third weekend of October, November and December. Each runs from 10 a.m. to 2 p.m., with reenactors showing what daily life was like inside a coastal fort.
This year's dates are Oct. 17–18, Nov. 21–22 and Dec. 19–20. The October weekend falls the week before Fantasy Fest, so the fort's first event of the season comes just ahead of the island's busiest week. The November weekend is the last one before Thanksgiving week. The December weekend lines up with the Little White House's busiest public day.
Dec. 19, when two calendars overlap
On Saturday, Dec. 19, the fort's Living History hours run from 10 a.m. to 2 p.m. The Truman Little White House Foundation holds its free Great Gingerbread Build that same day from 11 a.m. to 2 p.m. For three hours, the two biggest historic sites near the Annex are running public programs at once.
The rest of the Foundation's calendar runs on a different scale. The season opens with a members gathering on Thursday, Oct. 15, to watch a Truman Library Institute live stream titled "The Growing Risk of a Financial Crisis." It features Sheila C. Bair, who won the 2026 Truman Medal for Economic Policy and is described on the Foundation's page as Chair of the FDIC. Holiday tours and card presentations follow on Dec. 22 and 23. In January, the author Matthew Algeo gives the Truman Literary Series talk on Jan. 27. The next day he returns with artist Joanne Hasman for the Truman Art Series. On those weeknights in late January, the busiest place near the Annex may be a room of people talking about Harry Truman.
The Bight's December, a short walk east
The holiday season's main stretch runs along the harbor. The Key West "Bight" before Christmas schedule starts the Harbor Walk of Lights on Thanksgiving Eve, Wednesday, Nov. 25, at the Greene and Elizabeth Street plaza. Music starts at 5 p.m., the main tree is lit at 6, and a second lighting follows at Margaret Street at 7. The lights stay up through New Year's Eve.
The Thanksgiving dates line up neatly. The tree lighting is on Wednesday night, and the farmers market closes for Thanksgiving Day the next afternoon, its only skipped Thursday of the year.
December fills in from there. Pet Pictures with Santa comes to the Historic Seaport on Dec. 3. The city's Hometown Holiday Parade is on Dec. 5. The 35th Lighted Boat Parade moves along the Harbor Walk on Dec. 12. On Sunday, Dec. 20, a free Holiday Classic Car Show and toy drive takes over the Conch Republic Seafood Company parking lot on the Harbor Walk at Greene Street. That's the day after the Gingerbread Build, and the fort's December Living History weekend is still running.
Getting around, and a coffee stop on the way
One detail on the farmers market's homepage is out of date. The page still says the free Duval Loop stops near the waterfront. The Key West Citizen has reported that the city suspended the Duval Loop starting Jan. 2 and replaced it with Key West Rides. The new service is app-based, offers shared rides between designated bus stops, serves the old Loop stops, and covers both Key West and Stock Island. For the parade, where the route itself closes streets, walking will still be the most dependable option.
There is also a new stop on the walk. Baby's Coffee opened its new Old Town location on Fleming Street, across Bahama Street from Fausto's Food Palace, and customers were there by Sept. 1, 2026. Keys Weekly describes the building as a rebuilt former antique store.
The amphitheater's own listings currently show one confirmed date after the holidays. Yacht Rock Revue plays Coffee Butler Amphitheater on Wednesday, Jan. 20, 2027, with doors at 6 p.m. and the show at 7:30. It's the same stage that hosts the Headdress Ball, and both nights are a short walk from the Annex.
Terri, John, Ted and Lisa have watched many seasons roll past the Southard Street end of the parade route. If you're thinking about what life inside Truman Annex looks like from October through January, or about the parade-night logistics around a particular home in the Annex, The Spottswood Team is glad to talk it through.
