Key West Events
What's happening in Key West
Key West gets its own region for a reason. On paper it's MM 0 to 9, but really it's an island with its own personality and the densest event calendar in the Keys. Duval Street has live music day and night, often starting around 11 a.m. at the downtown bars with acoustic soloists and running well past midnight. The big annual stuff happens here. Hemingway Days in July, Fantasy Fest in October, the Goombay Festival the weekend before Fantasy Fest, the Sloppy Joe's Hemingway Look-Alike Contest, the Conch Republic Independence Celebration in April, the red shoe drop on New Year's Eve. Beyond the famous ones, there's a steady rhythm of First Thursday art walks, Pier House sunset celebrations, theater at the Red Barn and Waterfront Playhouse, and chamber stuff. If you can only check one region for what's happening tonight, this is the one.
Spotlight
Upcoming Events
Frequently asked questions
- What are the biggest Key West annual events?
- Hemingway Days in mid-July. Fantasy Fest the week ending the last Saturday of October. The Goombay Festival the weekend before Fantasy Fest. The Sloppy Joe's Hemingway Look-Alike Contest during Hemingway Days. The Conch Republic Independence Celebration in April. And the red shoe drop on New Year's Eve. Fantasy Fest is the wildest, Hemingway Days the most concentrated.
- Is Key West good for events year-round?
- Yes. Duval Street has live music every night. Fantasy Fest in October, New Year's Eve, and Spring Break are the busiest periods. Summer is hotter and quieter but never empty. May through August are the months locals reclaim the island.
Past Events
OCT
29
Slow Passage of Time ~ Culinary Experience In The Oldest House
OCT
25
The Hangover "But Did You Die?" Pool Party at Somo's Pineapple Pool
OCT
23
Southernmost Playboy House - Beach Bunny Pool Party Bash
OCT
21
FANTASY FEST SPOOKY TRIVIA - SOUTHERNMOST BEACH RESORT
OCT
21
ARTISTS DON ORIOLO AND RAY DREA APPEARING AT ZAZOO ART GALLERY FOR FANTESY FEST
OCT
20
TUTU SALSA SESSIONS
OCT
16
Fantasy Fest 2026: Key West's Wildest Ten Days
OCT
11
IF THE SHOE FITS 2nd-Annual NATIONAL FINALS Live in Key West!
OCT
4
OktoBREWfest Pool Party at Winslow's Bungalows
OCT
1
Ocean Key Resort & Spa | Autumn Glow Facial
Gay Key West, Inc. Announces First Official Fundraising Event at The Green Parrot
Ocean Guardian Family Day
JUL
21
Hemingway Days 2026
JUL
1
Key Lime Festival
JUN
21





