Florida Keys Events After Labor Day 2025

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Labor Day may close the book on summer for much of the country, but here in the Florida Keys, September and October are when the islands hit a special stride. The weather softens, the crowds thin, and the events? They’re as vibrant and quirky as ever. From epic open-water swims and charity fishing tournaments to foodie feasts and the costumed madness of Fantasy Fest, this is when locals and savvy travelers soak up the best of the Keys.

Here’s your detailed guide to what’s coming up, mile marker by mile marker:

🌊 September 2025

Every Thursday – Key West

Truman Waterfront Farmers Market
Every Thursday afternoon, the Truman Waterfront transforms into a slice of island living at its best. Picture tables piled high with tropical fruits, fresh-baked bread, colorful conch shell art, and live music floating in the salty breeze.

Set along the harbor by the USCG Ingham Museum, this market runs from 2–7 p.m. and feels more like a community gathering than just a shopping stop. It’s where locals catch up, chefs source ingredients, and visitors get a literal taste of the Keys.

Grab some mango jam, sip on fresh-squeezed sugarcane juice, and wander toward the pier to watch the boats roll in. If you’re lucky, you might catch a blazing Key West sunset as the market winds down.

• Address: At the Truman Waterfront

September 19–21 – Big Pine Key

Seacamp 60th Reunion
Down in the Lower Keys, Seacamp has been introducing kids and teens to the magic of the ocean for six decades. Alumni from across the country are coming “home” for a 60th reunion packed with snorkeling trips, bonfire stories, and dives into crystal waters.

If you’ve ever attended, you know this isn’t just a camp—it’s a launching pad for lifelong marine biologists, adventurers, and ocean lovers. This reunion will be equal parts nostalgia and new memories.

September 26–28 – Key Largo

Take Stock in Children Backcountry Challenge
If Islamorada is the Sportfishing Capital of the World, then Key Largo might be the heart of fishing with a purpose. This annual backcountry challenge isn’t just about catching trout, snook, and redfish—it’s about raising scholarships for local kids.

The tournament kicks off Friday night, with anglers heading out around the clock until Sunday afternoon. By the time the weigh-ins wrap, the weekend culminates in a lively Sunday dinner and auction that’s open to everyone. Even if you don’t fish, you can dine, bid, and help fund a student’s future.

• Facebook: Event Page

• Insider tip: Book a charter with a local guide if you’re new to backcountry fishing. You’ll not only support the cause but learn tricks you can use for years.

September 26–27 – Islamorada

Conch Scramble Charity Golf Tournament
Golf in Islamorada doesn’t involve manicured fairways or quiet greens—it involves boats, beer, and plenty of laughter.

In the Conch Scramble, golfers pile into boats instead of carts and “tee off” at holes spread across marinas, bars, and restaurants. Each stop is another round of fun, from Marker 88 to Lorelei and Oceanview Inn. Think of it as pub golf, Keys-style.

The festivities kick off Friday evening with a party at SD Marine (MM 85.5 bayside), and by Saturday, the waters are dotted with boats full of costumed players swinging away.

🍽 October 2025

October 1–31 – Key Largo

Taste the Keys
October in the Upper Keys is one long dinner party. Taste the Keys invites foodies to explore weekly trolley tours that bounce from restaurant to restaurant, each offering signature dishes and drinks.

Participating spots like Mrs. Mac’s, Skipper’s Dockside, Playa Largo, The Catch, and Gus’ Grille bring out their best, often with specials you won’t find any other time of year. The month culminates in a fiery cook-off where chefs battle it out for culinary bragging rights.

• Insider tip: Save room for dessert—Key Largo bakers love to put creative spins on the classic Key lime pie during this event.

October 16–19 – Key Largo

REEF Fest 2025
Love the ocean? REEF Fest is your tribe. Hosted by the Reef Environmental Education Foundation, this four-day celebration is a blend of eco-adventures and education.

By day, dive, snorkel, or kayak through Key Largo’s pristine marine sanctuaries. By night, gather for seminars and socials where conservationists, scientists, and ocean lovers swap stories and ideas. It’s equal parts fun and inspiring, with proceeds supporting REEF’s critical ocean protection efforts.

• Registration: Sign Up Here

• Must-do: Don’t miss the Saturday night banquet—it’s half celebration, half rallying cry for reef conservation.

October 17–19 – Islamorada

Ladies, Let’s Go Fishing!
Part workshop, part adventure, part party—this weekend is all about empowering women on the water. Beginners and seasoned anglers alike learn every style of fishing: offshore trolling, bottom fishing, inshore angling, and even fly casting.

With over 8,000 alumnae since its founding, this “university of fishing” is as much about camaraderie as it is about catching. The weekend culminates with the “Fishing Fever” tournament, where participants put their new skills to the test.

October 17–26 – Key West

Fantasy Fest 2025: “Bedtime Stories & Magical Monsters”
Ten days. Sixty thousand costumes. A thousand stories—most of which can’t be repeated outside the island.

Fantasy Fest is Key West’s biggest party of the year, and 2025’s theme invites everything from fairy tale whimsy to nightmare fuel. The island transforms into a nonstop carnival of parades, balls, concerts, and costume contests.

Key highlights include:

• Zombie Bike Ride – Oct. 19: Thousands of undead pedal down A1A, ending in a massive dance party.

• Masquerade March – Oct. 24: The locals’ parade, where costumes get creative and cocktails flow freely.

• Fantasy Fest Parade – Oct. 25: Glitter, floats, dancers, and 70,000 people filling Duval Street.

👉 Tickets: keystix.com/fantasyfest

• Insider tip: Book accommodations early. Fantasy Fest sells out fast, and even the campgrounds fill with revelers.

🌴 Ongoing Culinary Fun

Taste of the Keys (Aug 22 – Oct 31)
It’s not just in Key Largo—through October, restaurants up and down the Keys roll out special menus and unique flavors. Think lobster empanadas in Marathon, gourmet conch fritters in Key West, and mango-infused rum cocktails in Islamorada. A delicious excuse to island-hop.

✨ The Takeaway

While the rest of the country packs away beach towels and hauls out pumpkin spice, the Florida Keys are just getting warmed up. September and October bring a golden season—fewer crowds, cooler breezes, and some of the most colorful events of the year.

Whether you’re swimming to a lighthouse, golfing by boat, or pedaling through Duval as a zombie, there’s magic at every mile marker.

So—what’s calling your name this fall?

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