What To Do This Weekend in the Florida Keys: September 18-20, 2026

September in the Florida Keys keeps its momentum going into the middle of the month. The Grassy Key Paddle Battle takes over Grassy Flats Resort & Beach Club from Thursday, September 17 through Monday, September 21, and the glamour of Hush Money fills a Key Largo stage on Friday night. Lobster season is open, the water is warm, and the sunsets are on schedule. Here is what to do this weekend in the Florida Keys, September 18-20, 2026.

Friday, September 18

Grassy Key Paddle Battle: Day Two on Grassy Key

The Grassy Key Paddle Battle kicked off Thursday, September 17, so Friday is a full day of the action at Grassy Flats Resort & Beach Club. The week-long event brings water sports, wellness programming, paddle racing, and island adventure to Grassy Key, in the Marathon area of the Middle Keys. Even if you are not racing, the resort is a scenic spot to watch paddlers on the water, rent a board, or simply settle into the island pace. See the event calendar entry on the Visit Florida Keys website for the full schedule.

Kooky Key Largo Scavenger Hunt: Explore Key Largo by App

Kooky Key Largo Scavenger Hunt: An interactive, app-led scavenger hunt running through Key Largo on Friday and select weekend slots. It is a fun, family-friendly way to see the island's landmarks and hidden corners, with challenges you check off right from your phone.

Herman Lucerne Memorial Backcountry Championship: Final Days of the Tournament

Herman Lucerne Memorial Backcountry Championship: Wrapping up its final days (Sept 17–19), this unique fishing tournament takes place in the backcountry waters. Friday, September 18 is one of the last two days of the tournament, so it is a prime weekend to watch the anglers working the flats and backcountry around Key Largo.

Hush Money: A Glamour-Themed Friday Night in Key Largo

Friday night in Key Largo, Hush Money takes the stage at 8:30 p.m. This glamour-themed live performance is one of a Friday series that continues September 25 and October 9, 16, and 30, so there are several chances to catch the show. Confirm the venue and ticket details on the official Florida Keys event calendar.

From paddle racing to a glamorous encore, Friday is a classic Keys mix: salt water by day, live entertainment by night.

Saturday, September 19

Grassy Key Paddle Battle: Full Day at Grassy Flats Resort & Beach Club

Saturday is the heart of the Grassy Key Paddle Battle. The full day of paddle racing, water sports, and wellness activities unfolds at Grassy Flats Resort & Beach Club on Grassy Key, in the Marathon area. Spectators get a front-row view of the races, and participants should check in with the event organizers for start times and division details. Confirm the day's schedule on the Florida Keys event calendar before you head out.

If you want to stretch the day, Grassy Key sits a short drive from Marathon's restaurants and beaches. Sombrero Beach, the Seven Mile Bridge, and the working waterfront of the Middle Keys are all close by, and lobster season being open means a seafood dinner is never far away.

Boondocks Open-Air Market at Mile Marker 27.5

Boondocks Open-Air Market: Visit Mile Marker 27.5 on Saturday from 9:00 AM to 2:00 PM for local crafts, tropical food, and island vendors. It is an easy stop along the Overseas Highway, perfect for picking up island-made gifts and grabbing a bite between adventures.

Herman Lucerne Memorial Backcountry Championship: The Final Day

Herman Lucerne Memorial Backcountry Championship: Wrapping up its final days (Sept 17–19), this unique fishing tournament takes place in the backcountry waters. Saturday, September 19 is the last day of the tournament, so the backcountry sees its closing action this weekend.

Walk on White (Key West)

Walk on White (Key West): Stroll, sip, and discover Key West's creative side during this monthly art walk along White Street on Saturday, September 19. It features open art galleries, local studio tours, and complimentary drinks.

Son del Mundo Hispanic Heritage Event (Islamorada)

Son del Mundo Hispanic Heritage Event (Islamorada): Head to Islamorada starting at 6:00 PM on Saturday, September 19 to celebrate Hispanic Heritage Month with an evening of live Cuban music.

Pickles Pub Oktoberfest (Key West)

Pickles Pub Oktoberfest (Key West): For a lively block-party vibe, Green Street (between Duval and Ann Streets) is shutting down on Saturday from 12:00 PM to 6:00 PM for Pickles Pub's annual Oktoberfest celebration.

Tonio's Car Show (Summerland Key)

Tonio's Car Show (Summerland Key): Kick off your Saturday waterfront at Tonio's Seafood Shack & Tiki Bar (Mile Marker 24.5) from 12:00 PM to 3:00 PM on September 19. It's a classic keys gathering featuring hot rods, custom builds, and cold drinks.

Florida Keys Southernmost Car Club Cruise (Key West)

Florida Keys Southernmost Car Club Cruise (Key West): Following the show at Tonio's, the car club is hosting a secondary evening cruise into Key West from 6:00 PM to 10:00 PM on Saturday night.

Science Saturdays: Invasive Species (Key Largo)

Science Saturdays: Invasive Species (Key Largo): If you're in the Upper Keys, head to Key Largo at 11:00 AM on Saturday, September 19 for an educational community workshop focused on the impacts of invasive Lionfish.

Sunday, September 20

Grassy Key Paddle Battle: Weekend Wrap-Up

The Paddle Battle continues through Sunday, and the full event runs through Monday, September 21. That makes Sunday the last full weekend day of racing and island adventure at Grassy Flats Resort & Beach Club, with the grand finale still ahead on Monday for anyone who can stay.

The Herman Lucerne Memorial Backcountry Championship also wrapped up this weekend, closing out its final days (Sept 17–19) in the backcountry waters on Saturday, September 19. That leaves Sunday wide open for a boat day, a beach day, or a slow morning before sunset.

Relaxed Sunset Plans: the Old Seven Mile Bridge

Sunday evening is the time for the classic Keys sunset. Head to the Old Seven Mile Bridge in Marathon, where the historic spans frame one of the best golden hours in the Middle Keys. Walk or bike the old bridge section, find a spot along the rail, and watch the sky turn gold and pink over the water. It is a relaxed way to close out the weekend before the drive back up the Overseas Highway.

Florida Keys Farmers Market (Islamorada)

Florida Keys Farmers Market (Islamorada): Running every Sunday from 10:00 AM to 3:00 PM at Mile Marker 81, this casual market is great for picking up local produce, native plants, and artisanal crafts.

Local Live Music & Nightlife: All Weekend Long

Local Live Music & Nightlife: Venues along the main highway—such as Jimmy Johnson's Big Chill and Bayside Grille & Sunset Bar—host live bands and sunset celebrations all weekend long. Whether you close out Friday night or catch a Sunday band, the liveliest spots in the Upper Keys are an easy drive up and down the Overseas Highway.

More Keys Favorites: Ongoing Seasonal Picks

Spiny Lobster Season Is Open

Regular spiny lobster season in Florida runs from August 6 through March 31, which means it is open right now. That makes this prime time for a lobster hunt with a dive flag and a tickle stick, or simply a seafood dinner featuring local Keys lobster. Bag limits, size rules, and harvest regulations come from the Florida Fish and Wildlife Conservation Commission, so check the FWC website for the current rules before you head out.

A Classic Keys Fall Week

When the events pause, the Keys keep their own rhythm: sunset at the Old Seven Mile Bridge in Marathon, day trips for fishing charters and reef diving or snorkeling, and the weekend farmers markets. The Florida Keys Farmers Market fills Sunday mornings at the Islamorada Gardens Plaza at Mile Marker 81, and Key Largo's seasonal artisan market returns later in the fall. Any of these makes a great way to spend a September weekend in the Keys.

Event schedules and details may change. Confirm directly with event organizers before visiting.