Annual Events in the Keys
The big ones that come back every year, explained by the local newspaper.
Some events in the Florida Keys are so big they need more than a calendar listing. These guides cover the heavyweights: what they are, when they happen, what they cost and how to do them right. We keep each one updated as organizers announce dates, so bookmark the ones you care about and check back.
Key West · October
Fantasy Fest
October 16 to 25, 2026
Key West's 10-day costume blowout returns October 16-25, 2026. Here's the theme, the parade date and how to do it right.
Read the Guide →Key West · October
Goombay Festival
October 16 and 17, 2026
Bahama Village turns up the Junkanoo for two free days of island music, conch every way and the best food of Fantasy Fest week.
Read the Guide →Florida Keys · July
Lobster Mini Season
July 29 and 30, 2026
The two-day sport season hits July 29-30, 2026. Bag limits, the rules that get people ticketed, and how to stay safe out there.
Read the Guide →Florida Keys · October to May
Stone Crab Season
October 15, 2026 to May 1, 2027
Claws are back October 15. Season dates, the 2 7/8 inch rule, and why the crab always goes back in the water alive.
Read the Guide →Key West · January
Key West Half Marathon
January 15 to 17, 2027
13.1 miles at sea level, January 15-17, 2027. The race schedule, the course and how to train for wind instead of hills.
Read the Guide →Key West · Winter
Mile 0 Fest
Early 2027, dates announced with the lineup
A five-day Texas Red Dirt music festival at the end of the road. The 10th anniversary edition lands in early 2027, and badges go fast.
Read the Guide →Key West · Late April
Key West Songwriters Festival
Five days ending the first weekend of May
Two hundred of the people who actually wrote the hits, playing five days of mostly free shows all over Old Town.
Read the Guide →Marathon · March
Marathon Seafood Festival
March 13 and 14, 2027
The Middle Keys fishing fleet cooks its own catch one weekend every March. Five bucks gets you in the gate.
Read the Guide →Key West · December 31
Key West New Year's Eve
December 31, 2026
A drag queen in a giant red high heel, a six-foot conch shell and a pirate wench all drop at midnight. Pick your corner of Duval.
Read the Guide →Marathon · April
Seven Mile Bridge Run
A Saturday in April, 2027 date to be announced
One April morning a year, the Seven Mile Bridge closes to cars and 1,500 runners get it to themselves. Getting a bib is the hard part.
Read the Guide →Islamorada · February
Gigantic Nautical Flea Market
February 20 and 21, 2027
Four hundred vendors of boat gear, rods, reels and marine bargains, one weekend a year in Islamorada. Bring cash and a truck.
Read the Guide →Key West · July
Key Lime Festival
Fourth of July week every summer
Key West spends the Fourth of July week celebrating its official dessert, including a pie-eating contest where hands are not allowed.
Read the Guide →Key West · June
Key West Pride
Five days in early June
Five days in June, a street fair, and a parade up Duval in the town that once flew a rainbow flag from the Atlantic to the Gulf.
Read the Guide →Key West · December
Key West Lighted Boat Parade
Saturday, December 12, 2026
Decorated boats, a dark harbor and the whole Historic Seaport out on the docks. Free, and one of the best nights of December.
Read the Guide →Key West · January
Key West Food & Wine Festival
January 27 to 31, 2027
Five days of tastings, wine strolls and chef dinners across the island, in the best weather week of the Key West year.
Read the Guide →Key West · November
Key West Powerboat Races
November 1 to 8, 2026
Offshore race boats hitting triple digits in the harbor, three race days, and a parade of them down Duval to open the week.
Read the Guide →Lower Keys · July
Underwater Music Festival
July 10 and 11, 2026
A radio station broadcasts a playlist underwater at Looe Key Reef while divers in costume play fake instruments. Really.
Read the Guide →Key West · July
Hemingway Days
July 21 to 26, 2026
A bar full of white-bearded Papas competing to be the most Hemingway, plus a street fair and a running of wooden bulls.
Read the Guide →Key West · April
Conch Republic Independence Celebration
About ten days in late April
Key West seceded from the Union in 1982, declared war, surrendered in a minute and asked for a billion dollars. Every April it celebrates.
Read the Guide →Key West · October
Key West oktoBREWfest
Saturday, October 3, 2026, 3 to 8 p.m.
The island's big beer festival moved off Labor Day, picked up an Oktoberfest theme and packed 225 beers onto the beach.
Read the Guide →Key West · August
Key West Lobsterfest
August 5 to 9, 2026
Lobster season opens in August and Duval Street responds with a five-day festival ending in a giant free street fair.
Read the Guide →