Key West Events Calendar

The Key West Art Center

“Keys Season 2026” at the Key West Art Center

Oct 21 – Oct 25

Waterfront Playhouse

Hedwig and the Angry Inch

Wed–Fri|7:30 PM|Oct 21 – Oct 23

From $50

Key West Tropical Forest & Botanical Garden

Scarecrows and Skeletons in the Forest

Oct 21 – Oct 25

From $10

Key West Tropical Forest & Botanical Garden

Screaming Green Halloween (Copy)

This Saturday|9:00 AM

Key West Tropical Forest & Botanical Garden

StoryTime in the Garden

Tuesdays|10:00 AM|Oct 27 – Nov 24

Key West Tropical Forest & Botanical Garden

Native Plant Sale

Nov 7 – Dec 19

Waterfront Playhouse

Destroying David

Thu–Sat|7:30 PM|Nov 12 – Nov 14

$60

Tropic Cinema

Key West Film Festival

Nov 18 – Nov 22

Key West Tropical Forest & Botanical Garden

Pirates and Mermaids

Sat, Nov 21|10:00 AM

Waterfront Playhouse

It's A Wonderful Life: A Live Radio Play

Dec 2 – Dec 7

From $50

Key West Tropical Forest & Botanical Garden

Annual Speaker Series

Dec 19 – Mar 19, 2027

The Harry S. Truman Little White House

The Second Annual Great Gingerbread Build

Sat, Dec 19|11:00 AM

Free

The Harry S. Truman Little White House

Happy Holidays at the Little White House - Tour of House & Christmas Card Presentation

Dec 22 – Dec 23

From $20

Waterfront Playhouse

Blanche & Beyond

Thu–Sat|7:30 PM|Jan 7, 2027 – Jan 9, 2027

$70

Waterfront Playhouse

Unnecessary Farce

Jan 27, 2027 – Feb 2, 2027

From $50

Various Locations throughout Key West

Key West Food & Wine Festival

Wed, Jan 27, 2027|12:00 PM

Realty ONE Group Destination

VIP Welcome Party Realty ONE Group Destination

Wed, Jan 27, 2027|5:00 PM

$100

Various Locations throughout Key West

Key West Food & Wine Festival VIP Experience

Wed, Jan 27, 2027|12:00 PM

The Harry S. Truman Little White House

Truman Literary Series - "Harry Truman's Excellent Adventure" by Matthew Algeo

Wed, Jan 27, 2027|5:30 PM

From $20

The Key West Cooking Show

THE FIRST GAME OF FIVE "THE WINO GAME"

Thu, Jan 28, 2027|11:00 AM

$250