Party In Key West

Local’s Masquerade March
2026-10-23 00:00 - 02:00 (America/New_York) | Old Town Key West
The Local’s Masquerade March is a colorful neighborhood procession and one of Fantasy Fest’s most iconic local traditions.

Fantasy Fest Parade
2026-10-24 00:00, 2026-10-24 00:00 - 02:00 | Duval Street
Elaborate floats, costumes, and crowds fill Duval Street for the Fantasy Fest Parade, one of Key West’s biggest annual nights.

Children’s Day
2026-10-25 00:00, 2026-10-25 00:00 - 02:00 | Bayview Park
Children’s Day wraps Fantasy Fest with a family-friendly celebration featuring activities for children.

Garrison Keillor & Erica Rhodes
2026-10-27 00:00 - 02:00 | Key West Theater, 512 Eaton Street, Key West, Florida, 33040, United States
Garrison Keillor & Erica Rhodes performs at Key West Theater during the fall event season.

Garrison Keillor & Erica Rhodes
2026-10-27
Date(s): Oct 27, 2026Venue: Key West TheaterCategory: Comedy / Spoken WordPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1231478

Gathering of the Order of the Sleepless Knights
2026-10-28 00:00 - 2026-11-01 00:00 | Various Key West venues
A Key West music gathering celebrating trop rock artists and island music fans.

Gathering of the Order of the Sleepless Knights
2026-10-28 00:00 - 2026-11-01 23:59

Sunny Jim, Cayman Days
2026-10-29 00:00, 2026-10-29 00:00 - 02:00 | Key West Theater, 512 Eaton Street, Key West, Florida, 33040, United States
Sunny Jim, Cayman Days performs at Key West Theater during the fall event season.
