Upcoming Key West Events
Check out what's happening all around Key West, FL
Running of the Elves
Sat, 20 Dec at 06:00 pm
Key West
Key West Lighted Boat Parade 🎄
Sat, 13 Dec at 07:30 pm
631 Greene St, Key West, FL, United States, Florida 33040
Custom House Holiday Concert & Bazaar
Fri, 12 Dec at 05:00 pm
Key West Art & Historical Society
Holiday Lights Conch Tour Train
Fri, 12 Dec at 06:30 pm
Sigsbee Community Center
A Very Tutu Christmas Trolley 2025!
Mon, 15 Dec at 06:30 pm
504 Angela St, Key West, FL, United States, Florida 33040
Holiday Lighted Boat Parade
Sun, 14 Dec at 03:00 pm
The Perry Hotel & Marina Key West
31st Annual Taste of Key West
Mon, 23 Mar at 06:00 pm
Truman Waterfront, Key West, FL, United States, Florida 33040
Scrooge Macbeth - Opening Night
Tue, 09 Dec at 07:30 pm
319 Duval Street, Rear, 33040
Freedom Flotilla Festival
Fri, 19 Dec at 05:00 pm
Key West, Floirda
Lighting of the Menorah
Sun, 14 Dec at 05:30 pm
Bayview Park Key West
17th Annual Rudolph APSMC 5K
Sat, 13 Dec at 07:00 am
Southernmost Beach Resort
Reef Relief Annual Holiday Train
Wed, 10 Dec at 06:00 pm
631 Greene St, Key West, FL, United States, Florida 33040
Key west 2026: Free 21 days of Spiritual Meditation for Peace
Sat, 24 Jan at 08:45 pm
Virtual
Free
Pet Photos with Santa Qlaus and Nick Doll!
Sat, 13 Dec at 12:00 pm
Hank's Hair Of The Dog Saloon
December' Community Swim
Sat, 13 Dec at 06:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
Scott Kirby- 35 Years of Songs & Stories
Thu, 26 Feb at 07:00 pm
Key West Theater
Steven Rogers at Comedy Key West
Sun, 07 Dec at 08:30 pm
Comedy Key West
Scott Kirby- 35 Years of Songs & Stories
Fri, 26 Dec at 07:00 pm
Key West Theater
Key West Conch Train & Caroling
Tue, 09 Dec at 06:15 pm
Searstown
2026 Annual Southernmost Conch Republic POLAR PLUNGE
Sun, 08 Feb at 12:00 pm
Higgs Beach Key West, Florida
The Brit Pack: The Ultimate British Music Experience
Sat, 17 Jan at 08:00 pm
Key West Theater
Tim Palmieri & Friends at The Green Parrot
Fri, 12 Dec at 05:30 pm
The Green Parrot
Winter Party & Holiday Lights Trolley
Fri, 12 Dec at 06:30 pm
May Sands Montessori School
Holiday Bake Sale & Bazaar at Williams Hall
Sat, 13 Dec at 12:00 pm
729 Fleming Street, Key West, FL, United States, Florida 33040
Nature is Art: Children’s Art Workshop
Sat, 20 Dec at 10:00 am
5210 College Rd, Key West, FL
Great Gatsby NYE 2026
Wed, 31 Dec at 08:00 pm
First Flight Island Restaurant & Brewery
USD 269
Anthony Rodia at Key West Theater
Thu, 11 Dec at 08:00 pm
Key West
Florida Keys Seafood Festival
Sat, 14 Feb at 04:00 pm
Truman Waterfront Park
Cow Key Bridge ZERO-K Run
Sun, 19 Apr at 12:00 pm
Cow Key Channel Bridge
An Evening Aglow: A Candlelight Christmas with Marjory Lee
Tue, 16 Dec at 06:30 pm
Key West Theatre
Q West: Comedy Escape 2026
Fri, 10 Apr at 02:00 pm
Key West Theater
USD 450 to 534
🎄🔎 Murder at the Kringels - Murder Mystery
Thu, 18 Dec at 07:00 pm
5635 1st ave, Key West, FL, United States, Florida 33040
The Reverend Peyton's Big Damn Band
Sat, 21 Mar at 08:00 pm
Key West Theater
Rumours ATL: A Fleetwood Mac Tribute
Wed, 21 Jan at 08:00 pm
Key West Theater
IAN MAKSIN in KEY WEST, FL: "Lullaby for the World" New Album Release Tour
Sat, 03 Jan at 07:00 pm
Williams Hall
Mingle & Jingle - Holiday Cookie Crawl
Fri, 12 Dec at 03:00 pm
The Shops at Mallory Square
Southern Most HazMat Conference
Tue, 03 Feb at 08:00 am
3841 North Roosevelt Blvd., Key West, FL, United States, Florida
Kid's Crafts AT NIGHT: Elf Workshop
Wed, 10 Dec at 06:00 pm
Sigsbee Community Center
Follow The Rabbit... (9PM)
Sat, 13 Dec at 09:00 pm
Key West Theater
Sonic Sanctuary Sound Healing Journey
Fri, 19 Dec at 07:00 pm
508 Southard Street #107, Key West, FL, United States, Florida 33040
Freedom Flotilla Festival
Fri, 19 Dec at 05:00 pm
Key West
Free
December Duo Holiday Concert: Irie Monte and Crispin Campbell
Sat, 13 Dec at 06:00 pm
533 Eaton St, Key West, FL, United States, Florida 33040
Scott Kirby- 35 Years of Songs & Stories
Fri, 13 Feb at 07:00 pm
Key West Theater
Scott Kirby- 35 Years of Songs & Stories
Thu, 15 Jan at 07:00 pm
Key West Theater
Family Movie Night - A Polar Express Adventure
Fri, 19 Dec at 06:00 pm
Sigsbee Community Center
Put-in-Bay Days in Key West 2026
Wed, 11 Feb at 03:00 pm
Key West, Florida
Strategic Estate & Wealth Planning Meetup
Sat, 13 Dec at 04:00 pm
Salute! On The Beach
Free
Bobby in the Lobby
Sat, 07 Mar
Tennessee Williams Theatre
Truman Waterfront Farmers Market
Thu, 11 Dec at 02:00 pm
21 E Quay Rd, Key West, FL, United States, Florida 33040
2nd Saturday Celebration - Upstairs at Shops at Mallory Square
Sat, 13 Dec at 05:00 pm
The Shops at Mallory Square
The Linda Ronstadt Experience
Sat, 21 Feb at 08:00 pm
Key West Theater
Book Release Party: How Key West Killed JFK
Wed, 10 Dec at 05:00 pm
The Alex Vega Key West Firehouse Museum
Gabriel Rutledge Live in Key West
Sun, 15 Feb 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
TRANSFORMATION TEMPLE | New Moon • Winter Solstice Activation
Sat, 20 Dec at 06:00 pm
508 Southard Street #107, Key West, FL, United States, Florida 33040
Watercolor Fundraiser with Tracey DeLellis at Alonzo's Patio Bar
Mon, 15 Dec at 06:00 pm
Alonzo's Patio Bar
Santa Run + Pilates Wellness Event
Sat, 13 Dec at 08:00 am
Blue Flamingo Resort Key West
Free
Scott Kirby- 35 Years of Songs & Stories
Sat, 03 Jan at 07:00 pm
Key West Theater
Given to Fly- A Tribute to Pearl Jam
Sat, 10 Jan at 08:00 pm
Key West Theater
Meet The Candidates!
Thu, 11 Dec at 05:00 pm
Gardens Hotel
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
Santa Visits the Hemingway Home & Museum! ✨
Sat, 20 Dec at 12:15 pm
907 Whitehead Street, Key West, FL, United States, Florida 33040
Curry Ford West's Sleigh The Ford
Sat, 13 Dec at 12:00 pm
Curry Ford West
Sharese Nicole LIVE at Sunset Lounge Bar & Grill
Fri, 12 Dec at 05:00 pm
Sunset Lounge Sigsbee
Dvořák | Sibelius | Schubert - Key West
Sat, 14 Mar at 07:30 pm
Tennessee Williams Theatre
Duo Holiday Concert
Fri, 12 Dec at 06:00 pm
The Studios of Key West
Femmes of Rock at Key West Theater
Wed, 10 Dec
Key West Theater
General Membership Meeting & Awards
Wed, 10 Dec at 12:00 pm
Doubletree by Hilton Grand Key Resort
Mile 0 Fest Key West - 3 Day Pass (Thursday-Saturday)
Wed, 28 Jan at 07:00 pm
Truman Waterfront Amphitheater
Phil Collins Experience at Key West Theater
Mon, 26 Jan at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Christmas on the Farm Open House
Sun, 14 Dec at 01:00 pm
Monroe County Sheriff's Office Animal Farm
Steven Rogers
Sat, 06 Dec at 07:00 pm
Comedy Key West
Snowy Days Children’s Holiday Concert
Sun, 14 Dec at 12:00 pm
5210 College Rd, Key West, FL
Mile 0 Fest Key West - 5 Day Pass
Mon, 26 Jan at 07:00 pm
Truman Waterfront Amphitheater
Mile 0 Fest Key West - Tuesday
Mon, 26 Jan at 07:00 pm
Truman Waterfront Amphitheater
Cupid's Chase 5K Key West
Sat, 14 Feb at 09:00 am
Clarence S.Higgs Memorial Beach
USD 45 to 50
Key West Triathlon
Sun, 14 Dec at 05:30 am
Higgs Beach Key West, Florida
Petal-n-Palette Bubbles & Blooms - Holiday Floral Design Class
Sat, 20 Dec at 03:00 pm
The Gardens Hotel Key West Florida
Bliss body - Restorative Stretch
Sun, 14 Dec at 10:00 pm
508 Southard Street #107, Key West, FL, United States, Florida 33040
New Year's Eve at Four Marlins
Wed, 31 Dec at 05:30 pm
1435 Simonton St, Key West, FL 33040
Jesse Rice’s “Party At The Pier House” Show
Sat, 07 Mar at 05:00 pm
Pier House Resort & Spa
USD 36 to 180
Scott Kirby- 35 Years of Songs & Stories
Thu, 12 Feb at 07:00 pm
Key West Theater
Mile 0 Fest Key West - 3 Day Pass (Tuesday-Thursday)
Tue, 27 Jan at 07:00 pm
Truman Waterfront Amphitheater
Journal Medicine with Bliss // The Voice Within
Fri, 02 Jan at 07:00 pm
612 Fleming Street, Key West, FL, United States, Florida 33040
Sibelius | Ravel | Vaughan Williams - Key West
Sat, 24 Jan at 07:30 pm
Tennessee Williams Theatre
MINGLE & JINGLE at THE SHOPS AT MALLORY
Fri, 12 Dec at 03:00 pm
The Shops at Mallory Square
Peter Mayer & Friends- Album Release: Songs & Stories from the 12 Volt Man (7PM)
Sat, 17 Jan at 07:00 pm
Key West Theater
Native Plant Sale: Grow Your Own Habitat!
Sat, 20 Dec at 09:00 am
5210 College Rd, Key West, FL, United States, Florida 33040
Great Gingerbread Build
Sat, 13 Dec at 11:00 am
111 Front St, Key West, FL, United States, Florida 33040
Paradise Big Band at Tennessee Williams Theatre
Sun, 25 Jan at 07:30 pm
Tennessee Williams Theatre
61th Annual Key West Art & Craft Festival
Sat, 21 Feb at 10:00 am
Truman Waterfront Park
South Florida Symphony Orchestra - Sibelius at Tennessee Williams Theatre
Sat, 24 Jan at 07:30 pm
Tennessee Williams Theatre
SAM KAUFMAN FUN! RAISER - Sam Kaufman for Mayor of Key West
Sun, 21 Dec at 02:00 pm
Salute! On The Beach
🎟️ FINAL VVIP CALL: Graham Nash – Key West Night 1! | Apr 25, 2026
Sat, 25 Apr at 08:00 pm
Key West, Florida Keys
Business After Hours
Thu, 11 Dec at 05:30 pm
Rick's Bar
Scrooge Macbeth
Wed, 10 Dec at 07:30 pm
319 Duval Street, Rear, 33040
Gabriel Rutledge
Sat, 14 Feb at 07:00 pm
Key West Theater
Candlelight Yoga Nidra + Sound Bath with Malaika
Thu, 18 Dec at 07:00 pm
612 Fleming Street, Key West, FL, United States, Florida 33040
Donzel Leggett - Make Your Destiny Happen
Thu, 11 Dec at 06:30 pm
533 Eaton St, Key West, FL, United States, Florida 33040
Keys Choral Arts: Holiday Concert
Sat, 13 Dec at 07:00 pm
Tennessee Williams Theatre
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Upcoming Key West Events