Upcoming Festivals Events

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

 Hot Tin Roof Restaurant 9 Nov 2025
SPORTS USD 403 TO 805

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

 The Alamo Key West 5 Dec 2025
MUSIC

Wesley House Holiday Village & Bike Ride

 Coffee Butler Amphitheater 5 Dec 2025
CYCLING

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Upcoming Live Music Events

Buffett Through The Years

 512 Eaton St, Key West, FL, United States, Florida 33040 31 Oct 2025
CONCERTS

Mac McAnally in Key West

 Key West Theater 5 Dec 2025
CONCERTS

Mac McAnally in Key West

 Key West Theater 6 Dec 2025
CONCERTS

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Upcoming Comedy Events

Q West: Comedy Escape 2026

 Key West Theater 10 Apr 2026
COMEDY USD 450 TO 534

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

 Key West Theatre 21 Nov 2025
COMEDY

Anthony Rodia at Key West Theater

 Key West 11 Dec 2025
PERFORMANCES

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Upcoming Food & Drinks Events

Key West Powerboat Races 2025 - VIP Tent - FRIDAY

 Sunset Pier 7 Nov 2025
SPORTS USD 461 TO 518

THE MANGO MURDERS Brunch Sail *SOLD OUT*

 S/V Argo Navis 14 Nov 2025
BRUNCH

31st Annual Taste of Key West

 Truman Waterfront, Key West, FL, United States, Florida 33040 23 Mar 2026

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Upcoming Halloween Events

Golf Cart Facade Viewing Tour Fantasy Fest

 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040 29 Oct 2025
SPORTS

Glitter Witch Official Halloween Bar Crawl and Party

 504 Angela St, Key West, FL, United States, Florida 33040 31 Oct 2025
PARTIES

Trick or Treat Party at the Farmers Market

 21 E Quay Rd, Key West, FL, United States, Florida 33040 30 Oct 2025
TRICK-OR-TREAT

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Upcoming Thanksgiving Events

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 The Alamo Key West 21 Nov 2025
PARTIES

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

 Key West Theater 26 Nov 2025
PERFORMANCES

Time to Talk Turkey!

 291 Front St suite 207, Key West, FL, United States, Florida 33040 15 Nov 2025
WORKSHOPS

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Upcoming Pop-Ups Events

Truman Waterfront Farmers Market

 21 E Quay Rd, Key West, FL, United States, Florida 33040 30 Oct 2025
FARMERS-MARKETS

Follow The Rabbit... (6PM)

 Key West Theater 1 Nov 2025
PERFORMANCES

Key West 10th Annual Casino Night by SOS Foundation

 Beachside Resort & Residences Key West 14 Nov 2025
NONPROFIT USD 18 TO 135

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Upcoming Christmas Light Displays Events

Custom House Holiday Concert & Bazaar

 Key West Art & Historical Society 12 Dec 2025
MUSIC

Running of the Elves

 Key West 20 Dec 2025
SPORTS

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey

 Key West Theatre 14 Feb 2026

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Trending Events in Key West

Indoor Trick-or-Treat at Queer Keys Community Center

 1100 Truman Avenue, Key West, FL, United States, Florida 33040 29 Oct 2025
TRICK-OR-TREAT

2025 2nd Annual Family & Friends Love Cruise

 Bahamas 20 Nov 2025
CARNIVALS

Carnival Customer Appreciation

 Mallory Square Sunset Celebration, Key West, Florida 30 Nov 2025
CARNIVALS

Annual Tree Lighting

 Bayview Park Key West 30 Nov 2025
KIDS

Key West Powerboat Races 2025 - General Admission - Fri

 Sunset Pier 7 Nov 2025
SPORTS USD 71 TO 105

HEART LIFE MUSIC: An Evening in Conversation with Kenny Chesney

 5901 College Rd, Key West, FL, United States, Florida 33040 10 Nov 2025
CONCERTS

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

 Key West 5 Nov 2025
NIGHTCLUBS

David Sedaris

 Tennessee Williams Theatre 31 Oct 2025
ART

Key West Powerboat Races 2025 - VIP Tent - SUNDAY

 Sunset Pier 9 Nov 2025
SPORTS USD 461 TO 518

1st Annual USCGC Ingham Fundraising Gala

 Truman Waterfront Park - West end of Southhard Street, Key West, FL, United States, Florida 33040 22 Nov 2025
CHARITIES

Mac McAnally at Key West Theater

 Key West Theater 5 Dec 2025
CONTESTS

Fundraiser for Danny The Dragon!

528 Front Street, Key West, FL, United States, Florida 33040 31 Oct 2025
NONPROFIT

The Garcia Project Key West

 Key West Theater 512 Eaton St Key West, FL, 33040 5 Nov 2025
MUSIC

Keys Choral Arts: Holiday Concert

 Tennessee Williams Theatre 13 Dec 2025
CONCERTS

Dead Zep at Key West Theater

 Key West Theater 1 Nov 2025
TRIPS-ADVENTURES

More things to do in Key West

Festivals
Live Music
Comedy
Food & Drinks
Halloween
Thanksgiving
Carnivals
Pop-Ups
Christmas Light Displays
Trick Or Treat
Christmas Parades
Music Festivals
Parades
Bar Crawls
New Year
Christmas Carols