Key West Events

Jul
17
Tue
2018
Hemingway Days
Jul 17 – Jul 22 all-day
Hemingway Days

The 38th annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

Jul
18
Wed
2018
Havana Club Key West Marlin Tournament
Jul 18 – Jul 21 all-day

Anglers ply the waters once fished by writer Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Jul
21
Sat
2018
26th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race
Jul 21 all-day

This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.

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Look-Alike Contest
Jul 21 @ 5:30 pm – 9:30 pm

Sloppy Joe’s 38th Annual Hemingway (R) Look-Alike Contest click here for information and entry form.

Jul
23
Mon
2018
Preacher Pete & The Preference
Jul 23 @ 5:30 pm – 9:30 pm
Jul
26
Thu
2018
John LaMere
Jul 26 @ 12:00 pm – 4:45 pm
Aug
15
Wed
2018
Tropical Heat
Aug 15 – Aug 19 all-day
Tropical Heat

The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

Aug
30
Thu
2018
Ninth Annual Key West Brewfest
Aug 30 – Sep 3 all-day

More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities.

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Aug
31
Fri
2018
Heroes Salute Tribute Weekend
Aug 31 – Sep 2 all-day
Heroes Salute Tribute Weekend

Each fall, Hawks Cay Resort on Duck Key hosts an annual Heroes Salute program to honor military, fire and rescue, law enforcement and medical personnel; a special Labor Day Weekend event is planned to include an All-American barbecue, heroes tribute, country music concert and fireworks show.

Sep
5
Wed
2018
Womenfest 2018
Sep 5 – Sep 9 all-day
Womenfest 2018

Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

Sep
12
Wed
2018
Rock House
Sep 12 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
13
Thu
2018
Rock House
Sep 13 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
14
Fri
2018
46th Annual Phil Peterson’s Key West Poker Run
Sep 14 – Sep 16 all-day

Motorcyclists from throughout the United States are to travel one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (U.S. Highway 1), the 113-mile roadway from mainland Florida to Key West that features 42 bridges and long vistas of breathtaking open water.

Rock House
Sep 14 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
15
Sat
2018
Rock House
Sep 15 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
16
Sun
2018
Rock House
Sep 16 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
17
Mon
2018
Rock House
Sep 17 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Sep
18
Tue
2018
Rock House
Sep 18 @ 10:00 pm – 10:00 pm

On stage 10:00pm to 2:00am.

Oct
5
Fri
2018
SoMo Marathon & Half Marathon
Oct 5 – Oct 7 all-day

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 including a 10k and 5k are planned.

Oct
19
Fri
2018
39th Annual Key West Fantasy Fest
Oct 19 – Oct 28 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 marching groups, island-style bands and lavish floats. 

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