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

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

Sloppy Joe’s Boo Bash

Sat, 31 Oct at 09:00 am 201 Duval Street, Key West, FL

Four Week Inversions Clinic with Lauren J.

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

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

Halloween Bar Crawl 10/31 - KEY WEST

Sat, 31 Oct at 04:00 pm La Concha Key West, Autograph Collection

“Halloween Spooktacular” CommuniTEA Dance with Costume Contest benefiting MCC's Cooking with Love

Sat, 31 Oct at 04:30 pm Alexander's Guesthouse Key West

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