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12/27/2019 - 10:00am to 03/14/2020 - 4:00pm
The 60th Annual Key West Home Tours is the perfect opportunity to see some of the most exquisite homes on the island. This long-standing event first started in 1960 and has been running consistently ever since.
01/26/2020 - 10:00am to 02/02/2020 - 1:00pm
Celebrating its 11th year, the Annual Key West Food and Wine Festival offers five days of sought-after vintages and standout cuisine January 26 - February 2, 2020.
02/22/2020 - 10:00am to 5:00pm
The 55th Annual Old Island Days Art Festival is February 22 & 23, 2020 on Whitehead and Caroline Streets in Truman Annex.
02/29/2020 - 10:00am
Attend the 2020 Cow Key Zero K Bridge Run, which takes place on February 29, 2020, in Key West.
03/07/2020 - 8:00am
The annual Conch Shell Blowing Contest in March celebrates the history of conch shells in Key West.
03/28/2020 - 7:00am
Join 1,499 other running enthusiasts in this year's Annual 7 Mile Bridge Run in Key West, offering the best racing views around.
04/20/2020 - 6:00pm
Gather at Truman Waterfront for an evening of Key West's best food at the annual Taste of Key West.
05/06/2020 - 10:30am to 05/10/2020 - 11:30pm
The Key West Songwriters Festival is the largest festival of its kind featuring over 30 shows, 150 performers, and five days of music.
05/16/2020 - 6:00am to 05/17/2020 - 3:00pm
Run the 13th annual Keys100 Ultramarathon that takes you along the Florida Keys from Key Largo to Key West.
06/03/2020 - 5:00pm to 06/07/2020 - 10:00pm
Every June, the entire Key West community comes together to celebrate Pride. There will be free play readings, talent shows, pool parties, a street fair, and, of course, a big Key West Pride parade.