Sloppy Joe’s Boo Bash

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

Fri, 30 Oct at 05:00 pm Sebago Watersports

Will Kimbrough

Fri, 30 Oct at 05:00 pm Key West Theater

Key West vs. Barron Collier | Varsity Football

Fri, 30 Oct at 06:00 pm Key West, Florida Keys

The Cult Presents "The Lost Boys"

Fri, 30 Oct at 07:00 pm 416 Eaton Street, Key West, FL, United States, Florida 33040

Buffett Through the Years

Fri, 30 Oct at 08:00 pm Key West Theater

Tall Paul & Friends in Key West

Fri, 30 Oct at 09:00 pm Kaya Island Eats

Four Week Inversions Clinic with Lauren J.

Sat, 31 Oct at 09:30 am 612 Fleming Street, Key West, FL, United States, Florida 33040

Kids’ Paint & Plant Marigolds | October 31, 11 AM–1 PM

Sat, 31 Oct at 11:00 am 291 Front St, Key West, FL 33040-8367, United States

Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band

Sat, 31 Oct at 01:00 pm Key West Theater

The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31

Sat, 31 Oct at 01:00 pm TBA

Simonton Social District Block Party! (200 block)

Sat, 31 Oct at 02:30 pm 211 Simonton St., Key West, FL, United States, Florida 33040

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

Sat, 31 Oct at 04:00 pm Sebago Watersports

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