Most of Key West's big November dates fall within sight of the harbor. They start on the Outer Mole, where a national powerboat series ends its season, and close at the Historic Seaport, where a fishing-buoy tree and a lobster-trap tree light up the night before Thanksgiving. As the month goes on, the events become more local, and more of them are set up to send something back into the town.
Race Week Is Already Underway, and Friday Is the Big Day
The Race World Offshore Key West World Championship runs November 1 through 8, and the organizer bills it as the finale of its National Series, with Truman Waterfront Park as the base of operations. As of this Thursday, two race days remain on the posted schedule, Friday, November 6 and Sunday, November 8. The Race World Offshore schedule calls the race order "subject to change," and an earlier version of the event page also listed November 4.
On Friday, general admission gates open at Truman Waterfront Park at 9 a.m. The first race is set for 10 a.m. The Race Village runs 8:30 a.m. to 5 p.m., and the XINSURANCE VIP hospitality tents sit on the Outer Mole. Race World Offshore names Truman Waterfront Park and the Outer Mole as the spectator areas.
Getting there takes some planning. The organizer's FAQ says there is no parking within blocks of the Navy Mole entrance. It recommends rideshare, the free Duval Loop or a bicycle, and it notes that accessible parking is very limited and requires credentials. The evening street closures tied to the event matter even if you skip the races entirely. Here is what the October 1 City Commission agenda item lists for the rest of the week:
- Thursday, November 5, 6 to 10 p.m. Greene Street closed from Duval to Ann.
- Friday, November 6, 6 to 10 p.m. Duval Street closed from Front to Angela, and Greene Street closed from Telegraph Lane to Simonton.
- Sunday, November 8, 7 to 9 p.m. Awards ceremony at Coffee Butler Amphitheater.
At the Bight, the Florida Powerboat Club's Powerboat Village runs through Saturday, November 7, outside Conch Republic Seafood Co. on the Harborwalk, with the boats on display plus vendors, food, a happy hour and music. That is the week's link between the two ends of the harbor. The racing happens off Truman Waterfront Park, and the boats spend their evenings at the Seaport.
One Week Later, the Seaport Hosts Its First Oyster Fest
On Saturday, November 14, the Seaport holds an event of its own for the first time. The inaugural Key West Oyster Fest runs 5 to 10 p.m. in front of Half Shell Raw Bar. It is a collaboration between Half Shell, Everglades Oyster Company and Oyster Reefers, the team behind Miami's Oyster Fest.
The lineup draws heavily on restaurants from across the island. The Eventbrite listing names these partners:
- Oyster farms: Everglades Oysters, Indian River Oyster Co., Cypress Point Oysters and Pelican Oyster Co.
- Restaurants: Half Shell Raw Bar, Salt + Ash, Square Grouper, Hogfish Bar & Grill, Roostica, Alonzo's Oyster Bar, A&B Lobster, The Docks, Fishwife, Casa Marina, Cafe Marquesa and Papa Joe's Waterfront.
- Music: The Farm Boys.
Tickets start at $108.55. The listing includes unlimited raw or fire-grilled oysters, a premium open bar until 8 p.m., small bites, live auctions and music. The first hour, 5 to 6 p.m., is a VIP meet-and-greet with chef Norman Van Aken, and general admission opens at 6. Half Shell names Van Aken the festival's first ambassador and credits his early years cooking on the island with shaping the career that made him a pioneer of New World Cuisine. The Key West Citizen describes the event as a homecoming weekend for him.
The shells are what connect this festival to the rest of the month. Eventbrite lists Gulf Oyster Movement as the organizer and frames the evening as a benefit for Gulf oyster conservation, with proceeds going to shell recycling, support for farmers and culinary education. Every shell from the night will be collected for recycling. The festival also builds on recycling Half Shell already does. The restaurant says it recycles about 1,500 pounds of oyster shells a week with Everglades Oyster Company, and work is underway on a larger program that would bring in restaurants across Key West and Monroe County. A single festival night adds to that weekly total, and the goal behind it is a program that keeps shells out of the landfill and puts them to use in coastal restoration.
The Film Festival Goes Back to Eaton Street
For one week the action moves a few blocks inland. The 15th Key West Film Festival runs November 18 through 22 at the Tropic Cinema, 416 Eaton Street. The festival was founded there in 2012. The return depended on the theater itself coming back. KONK Life reported that the Tropic paused at the end of June, citing low attendance at independent theaters across the industry and lost revenue. On August 4, the Performing Arts Centers of Key West took over running the three-screen theater and set a reopening date of October 1. That nonprofit also runs the Tennessee Williams Theatre at the College of the Florida Keys.
KONK Life quoted festival founder and director Brooke Christian on the move:
"The Key West Film Festival is thrilled after so many years to be back at the Tropic – the festival's rightful home."
The full lineup, released October 28, adds a new "Florida and Friends" section of Florida-based films, including the Florida Keys premiere of First They Came for My College. The opening-night party is November 18 at the Truman Little White House. The festival's last film event, Occupational Hazard: The First Coral Reefers, is followed by a Coral Reefers performance at Smokin' Tuna, now at 313 Duval Street.
Other dates fill the middle of the month. The Veterans Day parade runs down Duval Street on November 11 from 4 to 6 p.m. The Waterfront Playhouse's Spotlight Series stages the Florida premiere of Destroying David November 12 through 14, according to Keys Weekly's season preview.
The Night Before Thanksgiving, Two Trees Light Up the Bight
Late in the month the calendar returns to the spot where Oyster Fest happened. The 21st annual Harbor Walk of Lights opens Wednesday, November 25, and it is free. The Key West Historic Seaport lays out the evening this way:
| Time | What happens | Where |
|---|---|---|
| 5 p.m. | Holiday music begins | Greene and Elizabeth streets |
| 6 p.m. | Fishing Buoy Christmas Tree lighting, with Santa and Mrs. Claus | Greene and Elizabeth streets |
| 6 p.m. | Music begins | Margaret Street plaza |
| 7 p.m. | Lobster Trap Christmas Tree lighting | Margaret Street plaza |
The Harborwalk stays lit every night through New Year's Eve. Key West Christmas notes that the lighting also starts the Cheryl Cates Toy Drive, so it marks the beginning of the island's holiday giving as well as its decorations.
The rest of Thanksgiving week is listed on the city calendar. The Southernmost Turkey Trot is Thanksgiving Day, November 26. The 32nd annual Hog Trot 5K follows on November 28, and the city's own Christmas tree lighting is November 30 from 6 to 8 p.m. at Bayview Park.
The Seaport's December is already booked, too. On December 3, All Animal Clinic hosts Pet Pictures with Santa at the Seaport's 16-foot Nautical Tree, with proceeds going to the Boys & Girls Club. Schooner Wharf Bar holds its tree-trimming party and toy drive on December 6. On December 12, the 35th Annual Key West Lighted Boat Parade starts with music at 6 p.m. and the parade at 8, with Schooner Wharf as the reviewing stand.
The waterfront that hosted race boats in the first week of November will be lit for decorated boats six weeks later.
Our team at Ocean Sotheby's International Realty spends this season along the same harbor, and we're glad to share what we know about the Bight, from the Outer Mole to the Margaret Street plaza. If you own on or near the harbor and want to know how your property compares in this market, request a home valuation and we'll prepare one for you.
