This Week in Key West: October 5 - October 11, 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 5 – October 11 , 2026.

🌟 This Week’s Highlights

🎵 Key West Musicians Fest

Saturday & Sunday, October 10 & 11 @ Key West EmPOURium — 2–9 PM
Enjoy free admission to a showcase of some of Key West’s best local musicians and songwriters!
618 Duval Street.

👢Line Dancing Class

Wednesday, October 7 @ 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 8 @ 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/

🧑‍🌾Key West Farmers Market

Thursday, October 8 @ Truman Waterfront — 1–6 PM
Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air setting. Browse seasonal produce, unique artisan goods, delicious food, and locally crafted finds while enjoying live music and the welcoming spirit of the Keys.
More info: https://keysartisanmarket.com/farmersmarket.htm

🌴 Our Concierge Pick

⛵ Schooner Sunset Sail

Nightly • Key West Harbor

Watching the sunset from the water is one of the most memorable experiences in Key West. Whether you prefer a classic schooner, a spacious catamaran, or a lively cruise with live music and cocktails, there’s a sunset sail for every style.

💡 Concierge Tip: Sunset sails are one of our most popular recommendations and often sell out—especially on weekends. Reserve early for the best availability.

👉 Book Your Sunset Sail: Key West Sunset Sail Options

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 5

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

Tuesday, October 6

• 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
• Party Knights @ Sloppy Joe’s— 10 PM

Wednesday, October 7

• Sharese @ Rams Head Southernmost— 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel— 5–7 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Tripp Fabulous @ Sloppy Joe’s— 10 PM

Thursday, October 8

• Robert Douglas @ Rams Head Southernmost— 11 AM–2 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Mac Calhoun & Colton Gleghorn @ Key West Empourium— 6 PM
• Tripp Fabulous @ Sloppy Joe’s— 10 PM

Friday, October 9

• Andy Westcott @ Rams Head Southernmost— 11 AM–2 PM
• Happy Hour All Day @ The Roost— 12–6 PM
• Marshall Morlock Band @ Key West Empourium— 8–11 PM
• The Fabulous Spectrelles @ Key West Empourium— 7 PM
• Shastina @ General Horseplay— 7 PM
• Tripp Fabulous @ Sloppy Joe’s— 10 PM

Saturday, October 10

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Key West Musician Fest @ Key West Empourium— 2–9 PM
• Zach Lovering @ General Horseplay— 7 PM
• Tripp Fabulous @ Sloppy Joe’s— 10 PM

• The Caffeine Carl Rounds with 7 Local Musicians @ Rams Head Southernmost— 12 AM–3 PM
• RNB Sessions with DJ Chaka @ General Horseplay— 2–4 PM
• Key West Musician Fest @ Key West Empourium— 2–9 PM
• John Dion @ The Gardens Hotel— 5–7:30 PM
• Marshall Morlock Band @ Key West Empourium— 8–11 PM
• Karaoke Night @ General Horseplay— 8 PM
• Tripp Fabulous @ Sloppy Joe’s— 10 PM