Key West Events

Sun Mon Tue Wed Thu Fri Sat
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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Jan 1 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing,[...]
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Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM! 9:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM!
Jan 6 @ 9:00 pm – 11:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s BarMonday Nights at 9 PM!Hosted by Comedy Key West’s Joe Madaus, Tony Hughes, and Steve Crane.Shot rounds, speed rounds and we don’t even know what else yet. It will[...]
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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Jan 8 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing,[...]
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Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM! 9:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM!
Jan 13 @ 9:00 pm – 11:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s BarMonday Nights at 9 PM!Hosted by Comedy Key West’s Joe Madaus, Tony Hughes, and Steve Crane.Shot rounds, speed rounds and we don’t even know what else yet. It will[...]
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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Jan 15 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing,[...]
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Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM! 9:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM!
Jan 20 @ 9:00 pm – 11:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s BarMonday Nights at 9 PM!Hosted by Comedy Key West’s Joe Madaus, Tony Hughes, and Steve Crane.Shot rounds, speed rounds and we don’t even know what else yet. It will[...]
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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Jan 22 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing,[...]
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Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM! 9:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM!
Jan 27 @ 9:00 pm – 11:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s BarMonday Nights at 9 PM!Hosted by Comedy Key West’s Joe Madaus, Tony Hughes, and Steve Crane.Shot rounds, speed rounds and we don’t even know what else yet. It will[...]
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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Jan 29 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing,[...]
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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

 

Sep
23
Fri
2016
Take Stock in Children Backcountry Challenge @ Key Largo
Sep 23 all-day

This 17th annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. A popular Sunday evening dinner and auction showcase is open to the public. Proceeds support local vocational scholarships for all ages, and Take Stock in Children scholarships for financially challenged Upper Keys students., Email: [email protected]

Sep
24
Sat
2016
Conch Scramble “On the Water” Golf Tournament @ Islamorada
Sep 24 all-day

Join an on-the-water wacky weekend charity golf tournament that brings together four-person teams to enjoy a game of nine holes by boat, to “drive” biodegradable golf balls toward floating greens – without any sand traps. A live or silent auction as well as a 50/50 cash raffle also are planned. Proceeds benefit local Keys charities., Email: [email protected]

Marathon International Bonefish Tournament @ Marathon
Sep 24 all-day

This challenge recognizes individual and team champions scoring the largest bonefish and permit, and 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”). The event is one of the few tournaments where anglers can fish without a professional guide., Contact: Barb 305-304-8682, Email: [email protected]

Sep
29
Thu
2016
REEF Fest @ Key Largo
Sep 29 all-day

Join Reef Environmental Education Foundation (REEF) in a celebration of marine conservation. Morning activities include ocean adventures of kayaking, snorkeling and diving, all alongside marine life experts. Afternoons feature free seminars from renowned experts in topics like Marine Mammals, Shark Behavior, Deep Sea Exploration and Emerging Ocean Issues. Evenings boast food, drinks and fun with friends old and new. All events are open to the public., Contact: 305-852-0030, Email: [email protected]

Oct
6
Thu
2016
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 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., Contact: 305-766-5284, Email: [email protected]

Oct
7
Fri
2016
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. In addition, music lovers can enjoy the stories behind yesterday’s favorites and today’s popular hits., Contact: Robert DiGiorgio 305-619-0172, Email: [email protected]

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 Apte, former Denver Bronco and Tampa Bay Buccaneer Mark Cooper and Major League Baseball Hall of Famer Wade Boggs., Contact: 305-664-2002, Email: [email protected]

Oct
9
Sun
2016
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 Oct. 9, fishing Oct. 10-12. One angler per boat pairs with a licensed captain to vie for division winners’ trophies. The three largest bonefish and three largest permit are to be scored by length, not weight., Contact: Betsy Bullard 305-587-1460, Email: [email protected]

Oct
12
Wed
2016
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 greatest male screen legend.” The festival, hosted by the screen legend’s son, Stephen Bogart, is the only event of its kind, and is backed by the Bogart Estate.

Oct
21
Fri
2016
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. The/2016 festival theme is “Political Voodoo and Ballot-Box Barbarians.”, Contact: 305-296-1817, Email: [email protected], Key West /10/23/2016, Key West Halloween Half Marathon and 5K Run, Competitors are encouraged to dress in their favorite costumes for this Halloween-themed running event., Email: [email protected]

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 recalling Key West’s Bahamian heritage.

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, bottom, inshore and fly fishing., Contact: Betty Bauman 954-475-9068, Email: [email protected]

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.