This Week in Key West: October 26 - November 1, 2026

Looking for things to do in Key West this week? Discover live music, local events, art walks, happy hours, nightlife, and island happenings taking place October 26 – November 1, 2026.

⭐This Week’s Featured Event

🎶Trop Rock’N Duval

October 28 through November 1, 2026
A vibrant, 5-day music festival taking over Key West from. Celebrating the island’s famous laid-back, beach-rock culture, this year’s festival features over 53 confirmed artists across 22 walkable venues right around the Duval Street area. Attendees can grab an official festival “Passport” to track performances, save shows, and fully immerse themselves in everything from classic tropical rock and reggae to heartfelt tributes honoring legends like Jimmy Buffett

🌟 This Week’s Highlights

👢Line Dancing Class

Wednesday, October 28 @ Key West EmPOURium — 6:30–8:30 PM
Dust off yer boots and learn to line dance. FREE.
More info: https://www.empouriumkeywest.com/

🎃Scarecrows & Skeletons in the Forest

All Month Long – Key West Tropical Forest & Botanical Garden
Scarecrows and skeletons, crafted from recycled materials, are made by local artists, students, and organizations. They are displayed throughout the Garden and are voted on by guests. Prizes are awarded to the winners.

🤓Jackpot Trivia

Thursday, October 29 @ Key West EmPOURium — 6–7:30 PM
Bring your besties and your brain power for a fun-filled night of trivia with host, Bill Hoebee. Free to attend. Win prizes! Sponsored by Pilar Rum and Bombara Vodka.
More info: https://www.empouriumkeywest.com/

🏠 Slow Passage of Time: A Culinary Experience inside the Oldest House

Thursday, October 29

Step inside the Oldest House after dark for an intimate evening of exceptional food, fine wine, and nearly 200 years of Key West history.
Start the evening at 6:00pm with an hors d’oeuvre & bubbles reception. At 7:00pm, gather round the table in our historic home for a five-course, wine-paired dinner prepared and served by award-winning chef, Juan Cuadra, of Salty Chef. Each course is thoughtfully prepared and presented, creating a memorable culinary experience within the intimate setting of one of Key West’s most historic homes.
With seating for just 10 guests, this is a truly intimate evening and a rare opportunity to experience the Oldest House as few visitors ever have.

Planning a future trip to Key West?

Browse festivals, concerts, races, holiday celebrations, and special events happening throughout the year.

View our complete 2026 Key West Events Calendar →

🎵 Live Music & Entertainment

Monday, October 26

• Nick Norman @ Rams Head Southernmost— 11AM–2 PM
• Mary Spear @ The Gardens Hotel— 5–7 PM
• Martinis w/ Melodic Beats @ General Horseplay— 9 PM

Tuesday, October 27

• Ross Brown @ Rams Head Southernmost— 11AM–2 PM
• John Dion @ The Gardens Hotel— 5–7 PM
• Glow Hours @ Hugh’s View atop Studios of Key West— 6–8 PM
• Screening of Hocus Pocus @ HiNote Bar— 6:30 PM
• Garrison Keillor and Erica Rhodes: “The Crazy Uncle and His Sensible Niece” @ Key West Theater— 8 PM
• Nightbreakers @ Sloppy Joe’s— 10 PM

Wednesday, October 28

• Sharese @ Rams Head Southernmost— 11 AM–2 PM
• A Pirate Looks Back: A Jimmy Buffett Tribute Show @ Comedy Key West— 12:30 PM
• Kenny Albert @ The Gardens Hotel— 5–7 PM
• TropRock’N Duval: Welcome to the Island Party @ Key West Empourium— 1–4 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Thursday, October 29

• Robert Douglas @ Rams Head Southernmost— 11 AM–2 PM
• TropRock’N Duval: Bahama Mama & The Painkillers @ Key West Empourium— 1-3 PM
• Sunny Jim, Cayman Days @ Key West Theater— 4 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• TropRock’N Duval: Dan Sullivan @ Key West Empourium— 5-8 PM
• The Lucky Ones @ General Horseplay— 9 PM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Friday, October 30

• Andy Westcott @ Rams Head Southernmost— 11 AM–2 PM
• Happy Hour All Day @ The Roost— 12–6 PM
• Sunny Jim, Cayman Days @ Key West Theater—1 PM
• TropRock’N Duval: Jim Morris Tribute (Scotty Bryan) @ Key West Empourium— 1-4 PM
• Will Kimbrough @ Key West Theater—4 PM
• TropRock’N Duval: Lucy & Nick DiBlasio @ Key West Empourium— 5-8 PM
• Shastina @ General Horseplay— 7 PM
• The Fabulous Spectrelles @ the Karaoke Lounge @ Key West Empourium— 7-8 PM
• Buffett Through the Years @ Key West Theater—8 PM
• TropRock’N Duval: Tall Paul & Friends @ Key West Empourium— 9 PM-12 AM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Saturday, October 31

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band @ Key West Theater—1 PM
• TropRock’N Duval: John Patti & Friends @ Key West Empourium— 1-4 PM
• Zach Lovering @ General Horseplay— 7 PM
• TropRock’N Duval: Tim Campbell & Tropical Attitudes Band @ Key West Empourium— 5–8 AM
• Jim Morris Tribute @ Key West Theater—7 PM
• TropRock’N Duval: Kelly McGuire & Friends @ Key West Empourium— 9–12 AM
• 52 Annual Halloween Contest @ Green Parrot Bar— 9–12 AM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Sunday, November 1

• Marjorie Lee @ Rams Head Southernmost— 11 AM–2 PM
• Andy Wescott Trio @ Green Parrot Bar— 1 & 3 PM
• Scott Marischen @ The Gardens Hotel— 5–7:30 PM
• Karaoke Night @ General Horseplay— 8 PM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM