Weirdest Key West Events

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Visitors and locals alike can agree that Key West is a city with rich history and character. With so many fun and unique events happening in the Keys, it can be hard to decide when to visit! So, we’ve decided to help out. Below you’ll find some of Key West’s more unique and colorful events that locals get to enjoy year after year. Join us as we name the best of the weirdest Key West events!

March

Conch Shell Blowing Contest (March 7, 2020, Noon)

Sponsored by the Old Island Restoration Foundation, this is one of Key West’s quirkiest events. Participants young and old gather at the Oldest House to see who has the best “Conch honk”. Entrants are judged on quality, duration, loudness, novelty, and, thankfully for most, NOT musical ability. Conch shells have long been a part of Key West history, with its earliest uses being a method of communication for Calusa Indians and a way for early Key West citizens to signal that a ship had wrecked off the coast of the island. Local islanders are now fondly known as Conchs (pronounced “Konk”).

April

Cow Key Channel Bridge Run (February 29, 2020, 10-2 pm)

Dubbed the “The Only Zero K Bridge Run”, this event takes place the day after the 7 Mile Mile Bridge Run every year. Key West locals have long been known as being on “island time” so this race doesn’t start until noon and, like true beach bums that Conchs are, no one breaks a sweat! The “run” starts on the Key West side of Cow Key Channel and ends with a party on the Stock Island side. The event is completed in stages with the first being “First Place Contenders” (the record to beat is 23.1 seconds) and the main event being “The Walking Cow Stampede”.

April

Conch Republic Independence Celebration (April 17-26, 2020)

As we mentioned above, Conch shells have long been part of Key West history. So much so that when the Florida Keys seceded from the United States in the 1980s, the new nation was named the “Conch Republic” and a conch shell is placed in a position of honor on the nation’s flag! Join local islanders in the celebration of Conch Republic independence with events including the Great Conch Republic Drag Race (with, you guessed it, Key West’s drag queens), Conch Republic Red Ribbon Bed Race (an open bed race down Duval Street), and even a battle at sea featuring the Conch Republic Navy throwing stale Cuban bread, sponges and vegetables at their enemies.

May

Annual Schooner Wharf Minimal Regatta (May 27, 2020, 1:30ish)

Key West has plenty of humor and quirks and this event is no different. A 6 person team must build a boat using only one sheet of plywood, two 2” x 4” boards, one pound of fasteners and one roll of duct tape. Painting is not required but is encouraged! After the build and vessel inspection, hilarity ensues as teams find out if their boat floats or sinks during the race. Awards given out include fastest, most creative, best costumes, and sinker awards. All entry fees for this event benefit the local VFW!

May

2nd Annual Papio Kinetic Sculpture Parade (April 4, 2020, Noon)

A new Key West tradition, participants of the Papio Kinetic Sculpture Parade participants compete for awards such as WeCycle’s Recycled Bicycle Award, the Pedal Pusher Award, and Papio on Wheels Award. The parade was started as dedication to Stanley Papio, a Florida Keys artist who saw beauty in junk. Known as “Barefoot Stanley” because he rarely wore shoes, Papio created amazing works of art by welding together old pieces of medal. In tribute, the Key West Art & Historical Society began the Papio Kinetic Sculpture Parade where participants would be asked to build moving sculptures in a style of work similar to Papio’s. Amazing sculptures featuring multiple moving parts, recycled materials, and sheer mechanical genius make up this unique Key West parade.

August

Key West Lobsterfest (August 6-9, 2020)

To celebrate the opening of lobster season, Key West hosts a huge party (in true Key West fashion). The four day event includes a lobster boil, street fair, bar crawl and free concert! Of course, no event on this island would be complete without something unique. Throughout the four days, you will see people who love lobster like no other including people sporting stuffed lobsters as hats! As well as local restaurants showing off their best lobster recipes, local artists take part in the street fair to show off their best pieces. It’s a great way to see what Key West has to offer!

October

Fantasy Fest (October 16-25, 2020)

One the most famous Key West events, Fantasy Fest, takes place around Halloween. The event welcomes anywhere from 25,000 to 75,000 people every year! The week long party includes parades, balls, AIDS benefits, body painting, drag queen contests and, of course, plenty of alcohol. Favorite events include the Zombie Bike Ride from East Martello to Duval Street, the local’s parade down Fleming Street, and the grand finale, the Fantasy Fest Parade including hundreds of beautiful costumes, sparkling floats, and amazing dance groups. Thousands of people wear costumes and body paint to attend the hundreds of parties happening all over Old Town. You don’t want to miss this one in a lifetime event!

There’s a reason why we’re nicknamed “Key Weird”! This crazy island is undoubtedly  one of the most unique cities in the country, it’s part of what makes the island so loved by locals and visitors. The island takes pride in its unique culture so come join us to celebrate the Conch Republic and all it has to offer!

If you’re ready to take part in some unique Key West events, check availability here! See a full list of our Key West events here, and check out our monthly calendar here.