Halloween in Key West

31Oct

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

TBA

31 Oct 2026

USD 8 TO 82

31Oct

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

TBA

31 Oct 2026

USD 8 TO 71

29Oct

The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29

TBA

29 Oct 2026

USD 8 TO 71

31Oct

Halloween Bar Crawl 10/31 - KEY WEST

La Concha Key West, Autograph Collection

31 Oct 2026

USD 20 TO 25

30Oct

Halloween Eve Bar Crawl 10/30 - KEY WEST

La Concha Key West, Autograph Collection

30 Oct 2026

USD 20 TO 25

1Nov

Mangoes Drag Brunch Royale Halloween Edition

Mangoes Restaurant

1 Nov 2026

USD 55 TO 66

30Oct

Asylum Circus Haunted House for all ages!

1908 Flagler Ave., Key West, FL

30 Oct 2026

31Oct

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

Key West Theater

31 Oct 2026

30Oct

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

Sebago Watersports

30 Oct 2026

28Oct

HOWLoween Pet Walk and Costume Contest

Sunset Lounge Sigsbee

28 Oct 2026

25Oct

80s & 90s Trivia Night Costume Party!

The Retro Room

25 Oct 2026

28Oct

Trunk or Treat

Fifth Street Baptist Church

28 Oct 2026

31Oct

Retro Room Halloween Party

126 Simonton Street, Key West, FL, United States, Florida 33040

31 Oct 2026

28Nov

Key West - Nov 27/28 - Edgar Allan Poe Speakeasy

Key West Theater

28 Nov 2026

31Oct

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

Alexander's Guesthouse Key West

31 Oct 2026

30Oct

Early Bird Clean Up Duval and Virginia hosted by Realty ONE Group (The Halloween edition)

Realty ONE Group Destination

30 Oct 2026

31Oct

Block Party with The Simonton Social District

211 Simonton St., Key West, FL, United States, Florida 33040

31 Oct 2026