Key West events October 2025

Things to do in October 2025 in Key West

With a bunch of festivals in October 2025 in Key West queued up, there is a lot to catch on! From being a spectator at all the cool festivals to attending some interesting events in October in Key West there is all the fun awaiting you this month. Take a tour to this interesting guide or list of things to do in Key West in October 2025 and make the most of your holidays and weekends!

Trending events in october in Key West

Amazing Scavenger Hunt Adventure - Key West, FL

Key West Historic Seaport, William Street, Key West, FL, USA

02 Aug Onwards

USD 49
2025 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery

Sat, 25 Oct
Clay Walker @ Country Music Cruise in Key West

Country Music Cruise

Wed, 29 Oct
Tay Tay Tuesday - In Your Wildest Dreams

Sunset Pier ~ Key West

Tue, 21 Oct
Peter Antoniou at Key West Theater

Key West Theater

Sat, 11 Oct
Pajama And Lingerie Party

Aqua Bar and Nightclub, Duval Street, Key West, FL, USA

23-24 Oct

Most popular events in october in Key West

Peter Antoniou

Key West Theater

Fri, 10 Oct
October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040

Sat, 11 Oct
That Arena Rock Show

0 Duval Street, Key West, FL, United States, Florida 33040

Sat, 18 Oct
25th Annual Living Art Expo

0 Duval Street, Key West, FL, United States, Florida 33040

Fri, 24 Oct
Mike Stack and Friends on the BIG stage at the Sunset Pier

Sunset Pier ~ Key West

Sat, 11 Oct
NightCaps and Nightgowns, a Moon Light Pajama Party

319 Duval St, Key West, FL, United States, Florida 33040

Sat, 25 Oct

Festivals in Key West

25th Annual Living Art Expo

0 Duval Street, Key West, FL, United States, Florida 33040

Fri, 24 Oct
Nine One Five's Fantasy Fest Parade Viewing Party

915 Duval St

Sat, 25 Oct
LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

Rick's Bar

22-23 Oct

View More

Parties in Key West

NightCaps and Nightgowns, a Moon Light Pajama Party

319 Duval St, Key West, FL, United States, Florida 33040

Sat, 25 Oct
Key West Halloween Drag Brunch Royale

Mangoes Restaurant

Sun, 19 Oct
Mrs. Roper Romp

Sunset Pier ~ Key West

Mon, 20 Oct

View More

Entertainment in Key West

That Arena Rock Show

0 Duval Street, Key West, FL, United States, Florida 33040

Sat, 18 Oct
Mike Stack and Friends on the BIG stage at the Sunset Pier

Sunset Pier ~ Key West

Sat, 11 Oct
Dave Matthews Tribute Band - FREE Show

0 Duval Street, Key West, FL, United States, Florida 33040

Fri, 17 Oct

View More

Music in Key West

October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040

Sat, 11 Oct
Tom Sandoval & The Most Extras

Key West Theater

Thu, 09 Oct
Clay Walker in Key West

Country Cruising

Wed, 29 Oct

View More

Events in October from nearby cities

Trending tags in Key West

dj-party 80s modelling tea sunday-funday parade body-painting psychedelic afrobeats running block-party street-fairs sea-food

Explore other popular categories in Key West

Entertainment

Parties

Music

Festivals

Live Music

Performances

Concerts

Art

Upcoming Events in October in Key West

Date	Event	Venue
04 Oct 2025	Phenomenal Animal at The Alamo Key West (Night 2 of 2)	The Alamo Key West
03 Oct 2025	Phenomenal Animal at The Alamo Key West (Night 1 of 2)	The Alamo Key West

All Events that you vibe with!

Customize your experience; only see the events that click with you!

Best in Key west, straight to your inbox

Never miss a single fun event; let us keep you updated!

Explore more in Key West

Events in October in Nearby Cities