September in the Keys: Locals' Season, Buffett Week, and a Brewfest That Moved

September is the month the Keys belong to the people who live here. The kids are back in school, the mini-season crowd is long gone, and you can get a table at 7pm on a Friday without knowing somebody. It is also the peak of hurricane season, half of Old Town is closed for "annual maintenance," and the water is still warm enough to cook in. All of that is true at the same time, and locals would not trade it.

We are already past the middle of the month, so this one is half recap, half heads-up on what is still worth planning around.

1. Buffett Week came and went (Sept 3 to 7)

The third annual Just a Few Friends festival took over Key West for Labor Day weekend. Cheeseburger cook-off on the beach, the city's Jimmy Buffett Day proclamation outside Shrimp Boat Sound, a look at the documentary still being made about that studio, and the Sunday second-line parade with the giant photo banners and the singalongs that nobody plans and everybody joins. Badge sales have raised more than $75,000 for Reef Relief, the Bahama Village Music Program, and local scholarships over the past two years.

Same weekend, Womenfest ran Sept 2 to 6 with a "Lost Women in the Arts" theme. Between the two, it was the busiest Key West gets all month, which still felt like a Tuesday in March.

• Local Tip: If you want to do Buffett Week next year, book the Casa Marina side of the island and bike in. Duval that weekend is fine. The parking is not.

2. Eight miles of open water (Sept 12)

The Swim for Alligator Lighthouse went off Saturday the 12th out of Amara Cay in Islamorada. Four miles out to the lighthouse, around it, four miles back, in September water, with a kayaker for company. Solo swimmers and relays. If you have ever stood at the end of a dock at 7am and watched a few hundred people wade in toward a speck on the horizon, you know why locals line the shoreline for this one. Registration for 2027 opens early and the relay slots go first.

3. The Poker Run just rolled out (Sept 16 to 19)

Peterson's Key West Poker Run, 44th edition, filled US 1 with motorcycles Wednesday through Saturday and turned eight blocks of Duval into a bike show. It benefits the Diabetes Research Institute and it is the loudest four days of the fall. If your ears are still ringing, that is normal.

• Local Tip for next year: Thursday and Friday are the days to avoid driving the Overseas Highway if you are on a schedule. Get where you are going before 10am or after dark.

4. Morada Way Art Walk (third Thursday)

September's walk was the 17th. The next one is Thursday, Oct 15, 6 to 9pm, between mile markers 81 and 82 in Islamorada. This is the one night a month the Upper Keys art crowd, the restaurant crews on their night off, and whoever wandered over from the bayside all end up on the same block. No parking hassle, no cover, decent live music. Go.

5. The "Gone Fishing" signs: who is closed, and until when

This is the part visitors never expect. A lot of Key West kitchens shut down for a few weeks in September so the staff can take a vacation and the owners can fix the walk-in. Per the Key West Citizen, here is where things stand:

• Louie's Backyard reopens Sept 24.
• Square Grouper on Caroline Street is dark until Oct 9.
• Blue Heaven reopens Oct 15.
• Salute! on the Beach is also on the closed list until the season picks back up.

Up the Keys, the Grassy Key Palm Deck stays closed until Nov 1. Before you drive 40 minutes for a specific place this month, call. The website is often the last thing that gets updated.

• Local Tip: The upside is that the places that stay open are running lean, friendly, and usually with a locals' special on the board. Ask.

6. Hurricane season, honestly

The statistical peak of Atlantic hurricane season was Sept 10, and the season runs through Nov 30. Most Septembers, nothing happens. Some Septembers, everything happens. Every local you know has a generator, a full tank, and an app open. If you are visiting: buy the travel insurance, keep an eye on the National Hurricane Center five-day outlook, and know that the Keys evacuate early and by zone. That is all. Do not let it stop you from coming. Do let it stop you from booking non-refundable anything in September.

7. On the water this month

The ocean is bathwater, the afternoons come with a thunderstorm, and the fishing is quietly excellent because nobody is out there. Mangrove and yellowtail snapper are steady on the patch reefs, the mahi are still around offshore if you are willing to run for them, and the flats start to fish well again as the water cools at the end of the month. Lobster regular season has been open since Aug 6, and with the mini-season crowd gone, the bugs and the boat ramps are both easier to get to.

What is coming, and why you should book now

• Key West Brewfest moved. For years it was the Labor Day weekend thing. Not in 2026. The Sunrise Rotary shifted it to Sept 30 through Oct 4, rebranded it "oktoBREWfest," and the Grand Tasting is Saturday, Oct 3, 3 to 8pm at Southernmost Beach Resort. Sixty-plus breweries, 200-plus beers, VIP gets in at 3 with a Bavarian buffet, general admission at 5. Proceeds go to the Rotary scholarship fund. If you were planning to skip it because you thought you missed it, you did not.
• REEF Fest, Key Largo, Oct 12 to 18. Dives, seminars, and the ocean-nerd social calendar of the year at the REEF campus at mile marker 98.
• Stone crab season opens Oct 15 and runs to May 1. Claws need to be 2 7/8 inches. Every fish house in the Keys has a line out the door that first week, and it is worth standing in.
• Fantasy Fest, Oct 16 to 25. This year's theme is "Musical Icons and Iconic Musicals," and the parade is Saturday, Oct 24, at 7pm on Duval. Rooms in Old Town for parade weekend are already thin. If you need one, stop reading and go book it.

The September Short List

• Sunset at Mallory Square with nobody in front of you. It happens maybe six weeks a year. This is one of them.
• Sombrero Beach on a weekday. Empty. Bring your own everything.
• The sandbars are still going every weekend, just with locals instead of tour boats. Wave.
• Hispanic Heritage Month runs through Oct 15, and the Cuban music nights in Key West are some of the best free things on the island right now. Check the city calendar.

Enjoy the quiet while it is here. Around the third week of October it is gone, and we will all be complaining about traffic again by Thanksgiving.