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 12 – October 18 , 2026.

⭐This Week’s Featured Event

🎉 Goombay Festival

Friday, October 16 & Saturday, October 17th — 12 PM–11 PM
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Emma Street and features nonstop musical entertainment ranging from reggae to soca. This is a family-friendly event. Noon to midnight; FREE.

🌟 This Week’s Highlights

👢Line Dancing Class

Wednesday, October 14 @ 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 15 @ 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 Artisan Market at Higgs Beach

Sunday, October 18 @ Higgs Beach —10:00-2 PM
Don’t miss the Key West Artisan Market at Higgs Beach, Fantasy Fest edition, Sunday, October 18th from 10 am to 2 pm! Shop fine crafts and art from talented Florida Keys makers, grab your official Fantasy Fest merch, and enjoy delicious international food trucks and stalls—plus refreshing adult beverages and live music! 1707 White Street at the corner of White Street and Atlantic. Admission is FREE!

🩻Zombie Bike Ride

Sunday, October 18 @ Higgs Beach —2 PM Gathering, 6 PM Ride
The Key West Zombie Bike Ride is a massive, family-friendly costumed bicycle cruise along the Atlantic oceanfront that kicks off the island’s annual Fantasy Fest with thousands of “undead” participants.

🌴 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

🎵 Live Music & Entertainment

Monday, October 12

• 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 13

• 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
• Tripp Fabulous @ Sloppy Joe’s— 10 PM

Wednesday, October 14

• 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
• Radio Hero @ Sloppy Joe’s— 10 PM

Thursday, October 15

• Robert Douglas @ Rams Head Southernmost— 11 AM–2 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Electric Blue Yonder @ Green Parrot Bar— 5–7 PM
• Mac Calhoun & Colton Gleghorn @ Key West Empourium— 6 PM
• Pierce August @ General Horseplay— 9 PM
• Radio Hero @ Sloppy Joe’s— 10 PM

Friday, October 16

• 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
• Radio Hero @ Sloppy Joe’s— 10 PM

Saturday, October 17
🎉Fantasy Fest Partys

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Zach Lovering @ General Horseplay— 7 PM
• Party in My Pants: A Sexy Ass Cabaret @ Key West Theater— 8 PM
• Marshall Morlock Band @ Key West Empourium— 8–11 PM
• Radio Hero @ Sloppy Joe’s— 10 PM

Sunday, October 18
🎉Fantasy Fest Partys

•Marjorie Lee @ Rams Head Southernmost— 11 AM–2 PM
• Cayman & Co @ Green Parrot Bar— 3 PM–6:30 PM
• John Dion @ The Gardens Hotel— 5–7:30 PM
• Xperimento- After Zombie Ride After Party @ Green Parrot Bar— 7–11 PM
• Jon Hollywood @ Key West Empourium— 8–11 PM
• Karaoke Night @ General Horseplay— 8 PM
• Radio Hero @ Sloppy Joe’s— 10 PM

🍹 Happy Hour Picks

• Doc’s on Duval — Daily, 4–6 PM
• Dragon & Rooster — Daily, 3–5 PM
• General Horseplay — Sun 12–3 PM · Tues & Wed 3–6 PM
• Half Shell Raw Bar — Daily, 4:30–6:30 PM
• Kaya Island Eats — Daily, 4–6 PM
• Mary Ellen’s Bar — Mon, Tues, Wed, Fri 3:30–5:30 PM · Thurs 3:30–5 PM
• The Roost — Daily, 4–6 PM
• Rams Head Southernmost Cafe — Daily, 4–6 PM

Looking for even more events throughout the year? Browse the complete Key West Events Calendar →

Planning a Future Trip?

Looking ahead? Browse our complete annual calendar of festivals, concerts, races, holiday celebrations, and special events.

👉View the Key West Events Calendar

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Bethany Smith-Martin

OurKeyWest Concierge & Vacation Planner at OurKeyWest

I came to Key West New Year's Eve, 1996 to be with my college sweetie who is from Key West. We have made a life of all things Key West. 🏝️

Latest posts by Bethany Smith-Martin (see all)

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