Key West Events

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SoMo Marathon & Half Marathon
SoMo Marathon & Half Marathon @ Key West
Oct 6 all-day
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[...]
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Fifth Annual Downtown Key Largo Songfest
Fifth Annual Downtown Key Largo Songfest @ Key Largo
Oct 7 all-day
A host of elite Nashville songwriters are to liven up three Key Largo stages during this Columbus Day weekend festival that features music in genres including jazz, blues, rock and roll, country and contemporary pop.[...]
Robert James Sales Baybone Celebrity Tournament
Robert James Sales Baybone Celebrity Tournament @ Islamorada
Oct 7 all-day
For the first time in 25 years, the second tournament in the Redbone Trilogy moves to Islamorada, and targets permit and bonefish to raise money for cystic fibrosis research. Past participants include legendary angler Stu[...]
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Islamorada Fall All-Tackle Bonefish & Permit Championship
Islamorada Fall All-Tackle Bonefish & Permit Championship @ Islamorada
Oct 9 all-day
Known locally as the “Fall All-Tackle,” the three-day fishing challenge attracts energized newcomers to face seasoned veterans, in a competitive format since 1970. Up to 25 participants can fish in the tournament; festivities kick off[...]
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Fourth Annual Humphrey Bogart Film Festival
Fourth Annual Humphrey Bogart Film Festival @ Key Largo
Oct 12 all-day
The fourth annual Humphrey Bogart Film Festival is to screen a rotating selection of Bogie classics and a group of movies celebrating the life and films of the man the American Film Institute named “America’s[...]
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37th Annual Key West Fantasy Fest
37th Annual Key West Fantasy Fest @ Key West
Oct 21 all-day
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars 3/ing groups, island-style bands and lavish floats.[...]
Goombay Festival
Goombay Festival @ Key West
Oct 21 all-day
Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors[...]
Ladies Let’s Go Fishing!” Annual Keys Fishing University for Women
Ladies Let’s Go Fishing!” Annual Keys Fishing University for Women @ Islamorada
Oct 21 all-day
Female fishing fans can learn or polish angling skills during the award-winning weekend seminar. More than 8,000 female graduates have immersed themselves in the lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore,[...]
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Fall Backcountry Fly Championship Series
Fall Backcountry Fly Championship Series @ Islamorada
Oct 29 all-day
Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where one inch equals one point. Awards are to be given to the grand champion and[...]
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Key West events are so much fun! There's always something going on in the Southernmost party city! So you're wondering what Key West things to do. Find what concert, musician, local bands and so much more on our Key West events party guide calendar.  Our Party in Key West destination guide will make your visit to Key West the best ever!

Key West Events

 

Oct
29
Sat
2016
Fall Backcountry Fly Championship Series @ Islamorada
Oct 29 all-day

Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where one inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish. The field is limited to 30 boats.

Nov
4
Fri
2016
Beach Road Trip Weekend @ Islamorada
Nov 4 all-day

This lively event features a large group of people taking a road trip to party on the beach, night and day, for an entire weekend. The festivities consist of uniquely themed all-inclusive parties with complimentary drinks and food, parking and shuttle service over a three-day span in Islamorada., Contact: 954-608-3131, Email: [email protected]

Robert James Sales Redbone Celebrity Tournament @ Key Largo
Nov 4 all-day

Celebrities join other anglers to catch bonefish and redfish to raise money for cystic fibrosis research in the final event of the annual Redbone Celebrity Tournament Series., Contact: 305-664-2002, Email: [email protected]

Nov
6
Sun
2016
35th Annual Key West World Championship Races @ Key West
Nov 6 all-day

Super Boat International returns with teams from all around the world who compete 4/through 10/in the National Series Points races and conclude in 11/for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 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, Email: [email protected], Key Largo /11/12/2016, Eighth Annual Key Largo Bridge Run, Runners can enjoy the sunrise where the Atlantic Ocean meets the Gulf of Mexico while participating in the out-and-back race that crosses a portion of the Florida Keys Overseas Highway, including the Jewfish Creek Bridge., Contact: 305-451-1642, Email: [email protected]

Nov
17
Thu
2016
Cheeca Lodge & Spa All-American Backcountry Tournament @ Islamorada
Nov 17 all-day

Anglers compete for prizes and trophies in this annual event targeting snook, redfish, bonefish, tarpon and permit. Proceeds benefit the Guides Trust Foundation. Highlights include a beachside barbecue and an awards banquet characteristic of Cheeca’s casual elegance., Contact: 360-288-2436 (PT), Email: [email protected]

Nov
23
Wed
2016
International Sand Art Competition @ Key West
Nov 23 all-day

Nontraditional artistry and beachside fun combine in a unique creative experience for participants and spectators. Visitors can watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving weekend on the Atlantic Ocean beach at the Casa Marina Resort, 1500 Reynolds St., Email: [email protected], Big Pine & the Lower Keys /11/26/2016, Big Pine & The Lower Keys Island Art Festival, Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside., Contact: 305-872-2411, Email: [email protected]

Dec
1
Thu
2016
Islamorada Sailfish Tournament @ Islamorada
Dec 1 all-day

The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel. d, Contact: Dianne Harbaugh 305-522-4868 , Email: [email protected], Key West /12/31/2016, New Year’s Eve Shoe Drop Celebration, The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne., Email: [email protected]

Key West Triathlon and Expo @ Key West
Dec 1 all-day

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Dec
4
Sun
2016
“Key West Tropical Forest and Botanical Garden Guest Speaker Series” @ "Key West"
Dec 4 all-day

“Enjoy garden tours

Jan
24
Tue
2017
“Waterfront Playhouse presents: The Trip to Bountiful” @ "Key West"
Jan 24 all-day

“American masterpiece about the universal pull that we all feel for “home.” Carrie Watts is an elderly widow

Feb
2
Thu
2017
“Christopher Peterson’s EYECONS” @ "Key West"
Feb 2 all-day

“A master of impersonations

“Cuda Bowl” @ "Key West"
Feb 2 all-day

“Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina

“Key West Garden Club Educational Lecture Series: Preparing for Zombie Apocalypse” @ "Key West"
Feb 2 all-day

“Educational lectures are open to the public

Feb
3
Fri
2017
“Civil War Heritage Days Festival” @ "Key West"
Feb 3 all-day

“Colorful Civil War re-enactments

“Islamorada Women’s Sailfish Tournament” @ "Islamorada"
Feb 3 all-day

“In this light-tackle challenge

“Randy Roberts Live!” @ "Key West"
Feb 3 all-day

“Female impersonator extraordinaire Randy Roberts brings a one man

“Swamp Guides Ball” @ "Islamorada"
Feb 3 all-day

“All-release tournament offers fishing for bonefish

Feb
4
Sat
2017
“23rd Annual Pigeon Key Art Festival” @ "Marathon"
Feb 4 all-day

“Artists and craftspeople are to exhibit their work from 10 a.m. to 5 p.m. daily at this weekend event

“Key West Gallery presents: The Collected Works of Peter Max” @ "Key West"
Feb 4 all-day

“With paintings on exhibition in hundreds of museums and galleries worldwide

Feb
7
Tue
2017
“Poor Girls Sailfish Tournament” @ "Key Largo"
Feb 7 all-day

“A large regional charity competition that typically draws more than 200 anglers