30 Sep Islamorada Event Calendar October 2026 Fall Things to do In Islamorada Events
Fall 2026 Events in the Upper Florida Keys
Fall is a brilliant time to experience the Florida Keys. The summer heat begins to ease, the blue-green waters are calling, and the Upper Keys calendar fills with art walks, fishing tournaments, festivals, and holiday traditions.
In Islamorada, the popular Morada Way Art Walk returns on October 15, November 19, and December 17, bringing local artists, music, food, and the community together in the heart of Islamorada. Anglers will also find plenty happening on the water, with numerous fishing tournaments throughout October and the Islamorada Sailfish Tournament on December 4.
Elsewhere in the Upper Keys, enjoy the 7 Mile Bridge Sunset Celebration in Marathon on October 10, Reef Fest in Key Largo from October 15–18, and the Mote Reef Revival Fest in Islamorada on November 20. December brings a little Keys-style holiday cheer with Lignumvitae Christmas on December 5.
Whether you’re visiting for the fishing, art, conservation, or simply an excuse to spend a few more days by the water, fall offers a wonderful glimpse into what makes the Florida Keys such a special place.
Planning a fall getaway? Island Villa Rentals offers beautiful vacation homes throughout Islamorada, putting you close to the events, restaurants, marinas, and blue-green waters that make the Keys unforgettable.
UPCOMING EVENTS IN THE FLORIDA KEYS
Fall is here in the Florida Keys! 🌴
There’s plenty happening from Islamorada to Key Largo and Marathon this season. Save these dates and enjoy some of our favorite local events:
🎨 October 15 | Islamorada
Morada Way Art Walk
🎣 October 9–18 | Islamorada
Fishing Tournaments — too many to name!
🌅 October 10 | Marathon
7 Mile Bridge Sunset Celebration
🐚 October 15–18 | Key Largo
REEF Fest
🎨 November 19 | Islamorada
Morada Way Art Walk
🐚 November 20 | Islamorada
Mote Reef Revival Fest
🎣 December 4–6 | Islamorada
Islamorada Sailfish Tournament
🎄 December 5 | Islamorada
Lignumvitae Christmas
🎨 December 17 | Islamorada
Morada Way Art Walk
Whether you’re here for the fishing, local art, conservation events, or simply another beautiful sunset, fall is a wonderful time to experience the Upper Keys.
Planning a Florida Keys getaway? Island Villa Rentals offers vacation homes throughout Islamorada and the surrounding Keys. Come stay awhile and experience island life like a local.
Island Villa Rentals
📞 305-664-3333 | 305-393-4433