Fall in the Florida Keys: Events and Offers

Fall in the Florida Keys is truly majestic. With the glow of a brilliant orange sunset, a backdrop of cool palm trees swaying in the breeze, and sparkling Gulf waters—you’ll agree that this is one of the best times to visit Tranquility Bay. For a limited time, you can even save up to 20% on fall stays at Tranquility Bay Resort.

Book now to avoid disappointment and below we’ve even highlighted some of the exciting events taking place this fall.

TB gazebo sunset no chairs

Fall Events in Marathon and Nearby Key West:

Marathon: September 19 – 22, Marathon International Bonefish Tournament

For more than 50 years, this challenge awards individual and team champions scoring the largest bonefish and permit, the top anglers in fly and grand slam divisions (for the top spin or fly angler who releases the largest bonefish, permit and tarpon “slam”), as well as the tongue-in-cheek “wet pants” champion titles for anglers wading from shore. Contact: Barb 305-304-8682 or email bnbfishing@comcast.net.

The Florida Keys: September 19 – 22, 41st Annual Phil Peterson’s Key West Poker Run
It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. New this year: Poker Run stops are to be open for riders starting Thursday, Sept. 19 through Sunday, Sept. 22; more Keys-wide events to be planned for the entire week; cash prize to the person wearing the oldest official Phil Peterson’s Poker Run T-shirt. Contact: 800-545-2561 or 305-235-4023.

Marathon: September 25-29, Florida Keys Birding & Wildlife Festival

Florida Keys Birding & Wildlife Festival. Marathon & the Lower Keys. A celebration of the natural wonders of Florida wildlife takes place at the peak of the fall birding season. The event includes field trips focusing on education and conservation relating to Keys birds and wildlife, nature photography, hikes, kayak excursions and a family-fun environmental fair. Visit www.keysbirdingfest.org or call 305-872-0774.

Key West: October 10 – 13, SoMo Marathon & Half Marathon
Presented by Pat Croce’s Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County. Email: liz@somomarathon.com

Marathon: October 19, Third Annual Stone Crab Eating Contest
The much-anticipated opening of Florida’s stone crab season takes place Oct. 15 each year, and the season opening is followed by this tasty test of crab-consuming capacity. How fast can you crack and cleanly consume 25 stone crab claws? Test your munching mettle at this zany contest. Register by 12 p.m., contest starts at 1 p.m., entry fee is $25 per contestant, and individuals must be at least 18 years old to enter. Interested eaters are encouraged to register early. Contact: 305-743-4353 or email keys.fisheries@comcast.net.

Key West: October 18 – 27, 34th Annual Fantasy Fest
This outrageous 10-day costuming and masking celebration, themed “Superheroes, Villains … and Beyond!” features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars marching groups, island bands and lavish floats. More than 40 masquerade contests, themed parties, parades and other spectacles are to challenge the creativity of mask and costume designers. Contact: 305-296-1817

Key West: November 3 – 10, Key West World Championship Race
High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 31st annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. Contact: 305-296-6166

Key West: November 13 – 17, Second Annual Key West Film Festival
Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. Contact: 941-527-9385

Key West: November 27 – December 31, Key West “Bight’ Before Christmas” Holiday Celebration
Live holiday music, games for the kids, holiday cheer and a chance for photos with Santa highlight this event along the historic harbor walk linking colorful seaport restaurants, bars and businesses at the Key West Bight. Created as a gift to the community, the gala is produced by the Key West Bight Preservation Association and tenants of the Key West Bight. Contact: 305-304-2633

Marathon: December 8, Key Colony Beach Lighted Boat Parade

Christmas lights on outriggers, Santa’s elves and brightly lit deck displays highlight the beautiful festivities during the Key Colony Beach Boat Parade, set to begin at the 7th Street canal. The parade is open to all boats, and the route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the dock area behind city hall and the post office. The public is welcome. An after-party with awards for captains and crews is to be held at Key Colony Inn with a free buffet and cash bar. Contact: 305-743-7214

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