Fall & Winter Events Near Key Largo

Fall and winter in the Florida Keys bring a vibrant mix of athletic challenges, marine conservation, community gatherings, and festive celebrations. From open-water swims and fishing tournaments to holiday festivals and ocean-focused expos, there’s something for everyone to enjoy. 

September Events

Fish & Friends Seminar

September 9, 2025 / REEF Ocean Exploration Center

Fish & Friends is a free monthly seminar series highlighting captivating, ocean-related talks by guest speakers. Each event offers an opportunity to enjoy refreshments, connect with others who share an interest in the ocean, and learn something new. For those unable to attend in person, the seminars are also available via live stream on Facebook.

 

Swim for Alligator Lighthouse

September 13, 2025 - Islamorada
This annual 8-mile open-water swim challenges solo swimmers and relay teams to swim 4 miles out to Alligator Reef Lighthouse, circle it, then return. Organized by the Fighting Manatee Masters swim club, the event supports the restoration and re-lighting of the 152-year‑old lighthouse.

 

Immerse Yourself! Creating a World-Class Museum

September 17, 2025 - History of Diving Museum - 7:00–8:00 PM
Co-founder Dr. Sally Bauer presents a deep dive into the 40‑year journey of building the History of Diving Museum, detailing the challenges faced collecting artifacts, designing exhibits, and preserving diving history. Attendees can join in person or virtually.

 

October Events

“Taste the Keys” Food Tour

October 1–31, 2025 - Various locations in Key Largo
A month-long culinary journey featuring sample-sized dishes paired with drinks across Key Largo venues, all included in one flat fee.

 

Stone Crab Season Begins

October 15, 2025 – May 1, 2026 - Throughout the Florida Keys
The much‑anticipated stone crab harvest opens mid‑October, kicking off a season of fresh local seafood across Keys restaurants, markets, and crab shacks. It marks the start of months filled with delicious regional cuisine and crab‑centric menus.

 

REEF Fest

October 16–19, 2025 - REEF Ocean Exploration Center
Celebrate REEF’s 10th annual marine‑focused festival with four days of ocean‑themed seminars, daily open house hours, guided eco‑tours, social mixers, happy hours, and a bayside gala event. Expect engaging sessions, conservation networking, and optional walking tours at Pennekamp Coral Reef State Park.

 

November Events

All‑American Backcountry Tournament

November 13–15, 2025 - Cheeca Lodge & Spa, Islamorada
This prestigious annual tournament, inspired by former President George H. W. Bush, invites anglers to fish for snook, redfish, bonefish, tarpon, and permit in a dramatic backcountry catch‑and‑release format. Proceeds benefit the Bonefish & Tarpon Trust, supporting conservation efforts for these iconic backcountry species 

 

Tour de Keys

November 22, 2025
Cyclists from across the country will gather on Saturday, November 22 for the Tour de Keys, an annual charity ride through the breathtaking scenery of the Florida Keys. Riders can choose between a 50-mile route from Marathon or a 100-mile trek from Key Largo, both ending triumphantly in Key West. The event supports local nonprofit partners, with every mile raising funds and awareness for important causes in the community.

 

16th Annual Light Up Key Largo

TBD / Murray Nelson Government and Cultural Center

Don’t miss the 16th Annual Light Up Key Largo where guests will enjoy a large tree lighting, train rides, Santa, vendors, food, games, and more!

 

December Events

Islamorada Holiday Fest

December 5, 2025 / Founders Park, Islamorada / 4 - 10 PM
Now in its 21st year, Islamorada Holiday Fest transforms Founders Park into a winter wonderland for one magical night. The event features the beloved 30-ton Snow Mountain, where kids can play in real snow under the stars. A towering 35-foot tree adds to the festive glow as it releases magical snowfall throughout the evening. Highlights include a lively holiday parade starting at 7:30 PM with floats, antique cars, and an appearance by Santa Claus himself. The event also hosts over 50 local artists. Fest-goers can also enjoy food vendors, live holiday performances, sweet treats from Santa’s Sweet Shoppe, and the adorable Mister Gingerbread Man and Miss Sugarplum Fairy contest for children under 8. Holiday Fest is a community celebration that marks the official start of the holiday season in the Upper Keys.

 

Islamorada Half Marathon & 10K, Rumrunner Run 5K/10K, and Beach N’ Beer Mile

December 13–14, 2025 / Islamorada
The 11th annual Islamorada Half Marathon & 10K weekend is a vibrant two-day celebration of fitness, community, and island life. The weekend kicks off with the Rumrunner Run 5K and 10K, offering scenic coastal routes and a festive atmosphere. A signature favorite is the Beach N’ Beer Mile, where runners tackle one sandy mile while stopping for a refreshing beverage at each quarter-mile mark. The main events, the Half Marathon and 10K, take place on Sunday, offering breathtaking ocean views and a high-energy finish line celebration. Known as the largest running event in the Upper Keys, the weekend blends athletic challenge with tropical fun, making it a must-do for both serious runners and casual participants.

 

New Year’s Eve Fireworks on Blackwater Sound

December 31, 2025 / Near Mile Marker 104, Key Largo
A family-friendly fireworks display launched over Blackwater Sound. Popular viewing spots include waterfront venues like The Caribbean Club and Sundowners, often offering festive menus and live music.

 

Stay at Ocean Pointe Suites

Join us this fall and winter in Key Largo for an unforgettable blend of adventure, conservation, and celebration. After days filled with adventure, relax and recharge at the all-suite comfort of Ocean Pointe Suites. Located on pristine waterfront grounds, our resort offers spacious accommodations, marina access, a heated pool, and resort-grade amenities, all just moments away from the area's top events. Book your suite today and make your Keys getaway extraordinary.