Halloween Costume Contests in Key West 2026

Explore The Best Of Pumpkin Costume Parties & Events in Key West

Fantasy Fest Street Fair & Costume Promenade

 Duval St, Key West, FL 33040, United States 23 Oct 2026

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

 TBA 31 Oct 2026
USD 8 TO 82

Zombie Night at Captain Tony's Saloon

 Captain Tony's Saloon Key West 18 Oct 2026

Cocktails for Animal Tails - A Fantasy Fest Party!

 Rick's Key West 20 Oct 2026

Halloween Eve Bar Crawl 10/30 - KEY WEST

 La Concha Key West, Autograph Collection 30 Oct 2026
USD 0 TO 16

Halloween Bar Crawl 10/31 - KEY WEST

 La Concha Key West, Autograph Collection 31 Oct 2026
USD 0 TO 16

Sloppy Joe's Comic Book Caper-ers Party

 Sloppy Joe's Key West 19 Oct 2026

Krewe de Krazy Life Meet and Greet and Costume Parts Exchange

 Galleon Tiki Bar 18 Oct 2026

Rockin' it as Cowboys, Cowgirls, and Indians

 Captain Tony's Saloon Key West 22 Oct 2026

Havana Cabana At Key West's Duck, Duck, Booze Pool Party

 Havana Cabana Key West 19 Oct 2026

Under the Sea Party

 Dante's Pool Bar & Restaurant 19 Oct 2026