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

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

Fri, 30 Oct at 05:00 pm Sebago Watersports

Key West Theater

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

Will Kimbrough

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

Halloween Eve Bar Crawl 10/30 - KEY WEST

Fri, 30 Oct at 05:00 pm La Concha Key West, Autograph Collection

The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30

Fri, 30 Oct at 07:30 pm TBA

Buffett Through the Years

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

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

The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31

Sat, 31 Oct at 07:30 pm TBA

Mangoes Drag Brunch Royale Halloween Edition

Sun, 01 Nov at 11:30 am Mangoes Restaurant

Trivia Night

Wed, 04 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Early Bird Clean Up Lower Duval Street co-hosted by Oldest House Museum & Gardens & The Saint Hotel

Fri, 06 Nov at 08:00 am Oldest House & Gardens Key West

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