Events in Key West
View our Key West Events calendar for activities and events going on each month in Key West and the Florida Keys.
Events in Key West for 2026
- Jul 21, 2026 - Jul 26, 2026
- Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
- Website Sloppy Joes
- 201 Duval Street Key West FL 33040
- Facebook Instagram
- Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. This event celebrates Hemingway’s life in Key West and enduring legacy in a way that’s as unique and spirited as the man himself.
- Jul 25, 2026 - Jul 26, 2026
- 37TH ANNIVERSARY HEMINGWAY 5K SUNSET RUN & KEY WEST BEACH N’ BEER MILE
- Website Southernmost Point
- Southernmost Point Key West FL 33040
- Key West Half Marathon E-mail
- Facebook Twitter Instagram
- Runners and walkers can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 25th and the Beer Mile on July 26th during the Hemingway 5k Sunset Run and Beer Mile. The athletic challenges are part of Hemingway Days!