Upcoming Key West Events

Check out what's happening all around Key West, FL

Mac McAnally in Key West

 Fri, 05 Dec at 08:00 pm Key West Theater

Key West Powerboat Races 2025 - VIP Tent - FRIDAY

 Fri, 07 Nov at 09:00 am Sunset Pier USD 461 to 518

Key West Powerboat Races 2025 - VIP Tent - SUNDAY

 Sun, 09 Nov at 09:00 am Sunset Pier USD 461 to 518

Key West Lighted Boat Parade 🎄

 Sat, 13 Dec at 07:30 pm 631 Greene St, Key West, FL, United States, Florida 33040

Wesley House Holiday Village & Bike Ride

 Fri, 05 Dec at 05:00 pm Coffee Butler Amphitheater

31st Annual Taste of Key West

 Mon, 23 Mar at 06:00 pm Truman Waterfront, Key West, FL, United States, Florida 33040

NOV 5-11 | 33rd ANNUAL KEY WEST POKER RUN

 Wed, 05 Nov at 09:00 am Key West

HEART LIFE MUSIC: An Evening in Conversation with Kenny Chesney

 Mon, 10 Nov at 07:30 pm 5901 College Rd, Key West, FL, United States, Florida 33040

Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY

 Sun, 09 Nov at 09:00 am Hot Tin Roof Restaurant USD 403 to 805

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 03:00 pm The Alamo Key West

Annual Tree Lighting

 Sun, 30 Nov at 05:30 pm Bayview Park Key West

THE MANGO MURDERS Brunch Sail *SOLD OUT*

 Fri, 14 Nov at 11:00 am S/V Argo Navis

Key West Powerboat Races 2025 - General Admission - Fri

 Fri, 07 Nov at 09:00 am Sunset Pier USD 71 to 105

Brews & Empanadas

 Fri, 14 Nov at 05:00 pm The Alamo Key West

Tails on Trails

 Sat, 08 Nov at 10:00 am 5210 College Rd, Key West, FL, United States, Florida 33040

1st Annual USCGC Ingham Fundraising Gala

 Sat, 22 Nov at 05:00 pm Truman Waterfront Park - West end of Southhard Street, Key West, FL, United States, Florida 33040

Nature is Art: Children’s Art Workshop

Sat, 15 Nov at 10:00 am 5210 College Rd, Key West, FL

Mac McAnally at Key West Theater

 Fri, 05 Dec at 08:00 pm Key West Theater

The Garcia Project Key West

 Wed, 05 Nov at 08:00 pm Key West Theater 512 Eaton St Key West, FL, 33040

Rum Infused | Mermaids Pirates in the Garden

 Sat, 22 Nov at 06:00 pm 5210 College Rd, Key West, FL, United States, Florida 33040

TEASERS STREET PARTY - KEY WEST POWERBOAT WEEK

 Fri, 07 Nov at 06:00 pm Teasers Key West

Mac McAnally in Key West

 Sat, 06 Dec at 08:00 pm Key West Theater

17th Annual Rudolph APSMC 5K

 Sat, 13 Dec at 07:00 am Southernmost Beach Resort

The Garcia Project: Performing classic Jerry Garcia Band Set Lists from 1976-1995

 Sat, 15 Nov at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

WHEEL OF THE YEAR releasing and remembering

 Sun, 09 Nov at 05:00 pm shakti yoga key west

Nature is Art: Children’s Art Workshop

Sat, 20 Dec at 10:00 am 5210 College Rd, Key West, FL

Q West: Comedy Escape 2026

 Fri, 10 Apr at 02:00 pm Key West Theater USD 450 to 534

Florida Keys Seafood Festival

 Sat, 14 Feb at 04:00 pm Truman Waterfront Park

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 Fri, 21 Nov at 09:00 pm The Alamo Key West

A work-in-progress preview screening of "The Life & Art of Eric Anfinson"

 Sun, 16 Nov at 07:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

A Celebration of the Songs of Pete & Wayne with Pete Jarvis and Friends

 Fri, 21 Nov at 08:00 pm Key West Theatre

RWO Championship Awards Ceremony

 Sun, 09 Nov at 06:00 pm Coffee Butler Amphitheater

Scott Kirby- 35 Years of Songs & Stories

Thu, 26 Feb at 07:00 pm Key West Theater

2026 Annual Southernmost Conch Republic POLAR PLUNGE

 Sun, 08 Feb at 12:00 pm Higgs Beach Key West, Florida

Wheeland Brothers

 Sat, 08 Nov at 08:00 pm Key West Theater

BOAT RACE WELCOME PARTY - RED ELVISES at The Alamo!

Mon, 03 Nov at 08:00 pm The Alamo Key West

Mac McAnally – Key West

 Sat, 06 Dec at 07:00 pm Mac McAnally – Key West, FL – December 6, 2025

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

 Wed, 26 Nov at 08:00 pm Key West Theater

Tom Taylor Takeoff Event

Thu, 06 Nov at 02:00 pm The Alamo Key West

Mac McAnally in Key West

 Thu, 04 Dec at 08:00 pm Key West Theater

Custom House Holiday Concert & Bazaar

 Fri, 12 Dec at 05:00 pm Key West Art & Historical Society

Changes In Latitude at Key West Theater

Tue, 03 Mar at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Cow Key Bridge ZERO-K Run

Sun, 19 Apr at 12:00 pm Cow Key Channel Bridge

Running of the Elves

 Sat, 20 Dec at 06:00 pm Key West

Truman Waterfront Farmers Market

 Thu, 06 Nov at 03:00 pm 21 E Quay Rd, Key West, FL, United States, Florida 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West, Floirda

Key West Theater Welcomes The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

 Sat, 29 Nov at 08:00 pm Key West Theater

Time to Talk Turkey!

 Sat, 22 Nov at 07:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

Southern Most HazMat Conference

 Tue, 03 Feb at 08:00 am 3841 North Roosevelt Blvd., Key West, FL, United States, Florida

Candlelight Yoga Nidra + Sound Bath Experience with Malaika

 Thu, 20 Nov at 07:00 pm 612 Fleming Street, Key West, FL, United States, Florida 33040

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

 Mon, 17 Nov at 07:30 pm Tennessee Williams Theatre

Jeannine A. Cook - IT'S ME THEY FOLLOW

 Fri, 07 Nov at 06:30 pm 533 Eaton St, Key West, FL, United States, Florida 33040

61th Annual Key West Art & Craft Festival

 Sat, 21 Feb at 10:00 am Truman Waterfront Park

Race World Offshore Vendor Village

 Wed, 05 Nov at 09:00 am Key West Outer Mole

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West Free

Farm Open House

 Sun, 09 Nov at 01:00 pm Monroe County Sheriff's Office Animal Farm

Bali Bar Party

 Fri, 07 Nov at 08:00 pm 325 Duval St, Key West, FL 33040-6565, United States

Keys Choral Arts: Holiday Concert

 Sat, 13 Dec at 07:00 pm Tennessee Williams Theatre

Time to Talk Turkey!

 Sat, 15 Nov at 07:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 07:00 pm The Alamo Key West

Black Friday Shopping Extravaganza

 Fri, 28 Nov at 10:00 am Truman Waterfront Park

The Alamo KW Welcome Party

 Mon, 03 Nov at 05:30 pm 4 Charles St, Key West, FL 33040-6504, United States

Performing for Key West Wedding

Sat, 29 Nov at 04:00 pm Key West Islands

Key West Powerboat Races 2025 - General Admission - Sun

 Sun, 09 Nov at 09:00 am Sunset Pier USD 71 to 105

7 Bridges : The Ultimate EAGLES Experience - Key West, FL

 Fri, 27 Mar at 08:00 pm Key West Theater

November's Community Swim

 Sat, 15 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Liberty Candle Making Class

 Mon, 17 Nov at 05:00 pm Sigsbee Community Center

Zack Seemiller: This Show Saves Lives

Sun, 16 Nov at 07:00 pm Key West Theater

Follow The Rabbit... (6PM)

 Sat, 13 Dec at 06:00 pm Key West Theater

Mac McAnally - Night 2 - SOLD OUT

 Fri, 05 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Early Bird Clean Up Virginia & Watson Streets hosted by Unity of the Keys

 Fri, 07 Nov at 08:00 am Unity of the Keys

LKGA Monthly Scramble Event

 Sun, 09 Nov at 07:30 am Key West Golf Club

Great Gatsby NYE 2026

 Wed, 31 Dec at 08:00 pm First Flight Island Restaurant & Brewery USD 269

Build-a-Bouquet

 Mon, 24 Nov at 06:00 pm Sigsbee Community Center

Key West Truman Waterfront Farmers Market @ Bayview Park

 Thu, 06 Nov at 02:00 pm Bayview Park

Kaleo Wassman and Friends

 Thu, 13 Nov at 07:00 pm General Horseplay USD 40

Wining For The Animals

 Tue, 18 Nov at 05:30 pm Doubletree-Grand Key Resort

FLO-RAW | Sloppy Joe's Key West

 Wed, 03 Dec at 10:00 pm Sloppy Joe's Bar

The Wheeland Brothers

 Fri, 07 Nov at 07:00 pm Key West Theater

Scott Kirby- 35 Years of Songs & Stories

Thu, 15 Jan at 07:00 pm Key West Theater

The Reverend Peyton's Big Damn Band

 Sat, 21 Mar at 08:00 pm Key West Theater

Mac McAnally - Night 3 - SOLD OUT

 Sat, 06 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

A Very Tutu Christmas Trolley 2025!

Mon, 15 Dec at 06:30 pm 504 Angela St, Key West, FL, United States, Florida 33040

The second annual Key West BookFest!

 Sat, 15 Nov at 10:00 am 700 Fleming Street, Key West, FL, United States, Florida 33040

Winterfest

 Thu, 04 Dec at 04:00 pm Sigsbee Community Center

Mac McAnally at Key West Theater

 Thu, 04 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

28th Annual Key West Half Marathon & Runfest

 Fri, 16 Jan at 02:00 pm Key West Historic Seaport

Petals & Pearls | Celebrate 90 years in the Garden

 Fri, 30 Jan at 06:00 pm 5210 College Rd, Key West, FL, United States, Florida 33040

Italian Night at the Movies: The Bicycle Thief

 Wed, 05 Nov at 05:30 pm Tropic Cinema

Full Moon Magic Ghost Stories

 Wed, 05 Nov at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

ECSTATIC DANCE KEY WEST

 Thu, 20 Nov at 07:00 pm Kava Culture - Key West

Thanksgiving at Four Marlins

 Thu, 27 Nov at 05:30 pm 1435 Simonton St, Key West, FL 33040

The Brit Pack: The Ultimate British Music Experience

Sat, 17 Jan at 08:00 pm Key West Theater

Crystal Gayle at Key West Theater

 Sat, 22 Nov at 08:00 pm Key West Theater

CrossFit Mile Zero Cohen Weightlifting Seminar

 Sat, 17 Jan at 09:00 am CrossFit Mile Zero USD 82

Thomas Dolby at Key West Theater

 Fri, 07 Nov at 08:00 pm Key West Theater

Hog’s Boats & Ghosts World Championship Party

 Thu, 06 Nov at 07:30 pm 400 Front St, Key West, FL 33040-6617, United States

Anthony Rodia: Laugh Until it Hurts at Key West Theater

 Thu, 11 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Scott Kirby- 35 Years of Songs & Stories

 Fri, 26 Dec at 07:00 pm Key West Theater

Swing Dance Night with The Paradise Swing Band at Williams Hall

 Tue, 04 Nov at 07:00 pm 729 Fleming Street, Key West, FL, United States, Florida 33040
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