The first event after Fantasy Fest is on Duval Street. On Sunday, Nov. 1, at 4 p.m., the First State Bank World's Fastest Boat Parade rolls down the same street that just hosted the masks and floats. After that, the island's November calendar moves away from Duval. Nearly every event between the boat parade and Thanksgiving sits near the water: Truman Waterfront Park, the Outer Mole, the Key West Bight, Higgs Beach and the Southernmost Point Buoy.
By the night before Thanksgiving, that waterfront calendar has become the holiday season. The Harbor Walk of Lights goes on at the Bight on Wednesday, Nov. 25, five days before the City's own tree lighting and more than two weeks before the Lighted Boat Parade. Here is the month in order.
Week one belongs to the boats
Race World Offshore's Key West World Championship runs Nov. 1 through 8, with Truman Waterfront Park as its base. The organizer names Truman Waterfront Park and the Outer Mole as viewing locations. General admission gates are at Truman Waterfront, and the separate XINSURANCE VIP hospitality area is out on the Mole.
For people who live here, the week's street closures matter as much as the race days. The City Commission agenda item for the event, item 26-5889, lists the following:
Date | What's happening | Where |
|---|---|---|
Sun., Nov. 1 | World's Fastest Boat Parade, 4 p.m., rolling closure | Duval Street |
Wed., Nov. 4 | Race day | Truman Waterfront Park, Outer Mole |
Thu., Nov. 5 | Testing day; Greene Street Party, 6 to 10 p.m. | Greene between Duval and Ann |
Fri., Nov. 6 | Race day; Block Party, 6 to 10 p.m. | Duval between Front and Angela; Greene between Telegraph Lane and Simonton |
Sat., Nov. 7 | Testing day | Truman Waterfront Park |
Sun., Nov. 8 | Race day; awards ceremony | Coffee Butler Amphitheater |
The awards ceremony has two different times on record. The City's agenda item and calendar list 7 to 9 p.m., and Race World Offshore's published schedule shows 6 to 8 p.m. If you plan to be at the amphitheater on Sunday evening, check the time closer to the date.
Race World Offshore says there is no parking "within blocks" of the Navy Mole entrance. It recommends a rideshare or a bicycle and notes that handicap parking is very limited. From most of Old Town, walking or biking to Truman Waterfront takes less time than looking for a parking space.
The second Saturday moves to the Bight
The Bight's first big night of the month is the inaugural Key West Oyster Fest on Saturday, Nov. 14. The Historic Seaport's event page lists Half Shell Raw Bar, Everglades Oyster Company and Oyster Reefers as collaborators. The City of Key West's November calendar lists it from 5 to 11 p.m. in the Key West Bight parking lot in front of Half Shell.
Because it is the first Oyster Fest, there is no earlier year to compare it with, and the event page doesn't list an admission price or a beneficiary. The location is familiar, though. Eleven days later, the same stretch of harbor front is where the holiday season starts.
Film Festival week, with the lineup still to come
The 15th annual Key West Film Festival runs Nov. 18 through 22. The festival says it will announce its lineup, including Opening Night, Centerpiece and Closing Night films and the full slate, in October. Golden Key honorees are listed as pending.
The first look at the program comes at the free launch party on Tuesday, Oct. 27, at 6:30 p.m. at General Horseplay. Seating is first-come, first-served, and the evening includes a preview of the lineup. If you buy passes early or want certain screenings, that night is the one to attend, a few days after the last Fantasy Fest crowds leave.
The weekend of Nov. 21 and 22 starts on the waterfront and ends at Higgs
The last weekend of Film Festival week also has two outdoor events, one on each side of the island. On Saturday, Nov. 21, Tour de Keys 2026 is at Truman Waterfront Park from noon to 7 p.m. On Sunday morning, the Key West Half runs from 6 to 10 a.m., starting and finishing at Higgs Beach.
If you live along the Atlantic side between Casa Marina and White Street, Sunday morning is the time to watch for runners and closures. Most of the city's November events stay close to the harbor, and the Half is the main exception.
Thanksgiving week, in order
The holiday stretch starts on Wednesday, and nearly all of it happens outdoors and near the water:
- Wednesday, Nov. 25, Bight Before Christmas. The organizers' 2026 schedule starts music at 5 p.m. The main Fishing Buoy Christmas Tree lights at 6 p.m. at Greene and Elizabeth streets, the Harbor Walk of Lights goes on, and the Lobster Trap Christmas Tree at the Margaret Street plaza lights at 7 p.m. The City's calendar lists the Lobster Trap Tree lighting at Key West Historic Seaport and Marina from 6 to 7:30 p.m.
- Thursday, Nov. 26, the 4th Annual Southernmost Turkey Trot. The 5K starts at 8 a.m. and the 1 Mile Rooster Romp at 8:10 a.m. The organizer names the Southernmost Point Buoy as the start and finish. The City's street-closure listing places it at South and Duval streets.
- Saturday, Nov. 28, the 32nd Annual Hog Trot 5K. It starts at 8 a.m., and the City's listing puts the start of the route on Front Street.
- Monday, Nov. 30, the City's Annual Christmas Tree Lighting Ceremony. The City calendar lists it at Bayview Park from 6 to 8 p.m.
The harbor front lights up on Nov. 25, and the City's own ceremony in Midtown follows on Nov. 30.
Where December picks up
The waterfront season peaks on Saturday, Dec. 12, with the 35th Annual Key West Lighted Boat Parade. Music starts at 6 p.m. and the parade at 8 p.m. Spectators watch along the Historic Seaport Harbor Walk of Lights, and the reviewing stand is at Schooner Wharf Bar and Galley. The parade passes the same lights and the same lot that hosted Oyster Fest a month earlier.
Indoors, Red Barn Theatre opens its 47th season with "Shooting Star," which runs Dec. 8, 2026, through Jan. 2, 2027, with 7 p.m. performances, according to the theater's announcement.
The tables are back, too
The calendar fills up at the same time as the island's dining rooms. Many Key West restaurants close for a few weeks in late summer, and Key West Food Guide's running 2026 list tracks when they come back. According to that list, Moondog Cafe reopened Sept. 3, and Louie's Backyard returned for dinner on Sept. 24. Cafe Sole and Seven Fish both reopened Oct. 1, and Fisherman's Cafe came back on Oct. 5. The same list gave Blue Heaven a scheduled reopening date of Oct. 16. Azur was expected back in mid-October and Frenchie's Cafe in the third week of the month.
There is also a new option. Keys Weekly reported on Sept. 4 that Baby's Coffee had opened a new Old Town location on Fleming Street. That gives early risers heading to Higgs for the Half, or to the buoy on Thanksgiving morning, another place to get coffee first.
If you're planning November around the races, the Bight or a Thanksgiving morning run, and you also have questions about the island itself, The Spottswood Team is glad to help you sort out the details. Get in Touch.
