This Week in Key West: June 22–28, 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 June 22–28, 2026.

🌟 This Week at a Glance

🎟️ Summer Bingo Night – June 17
🎨 Walk on White – June 18
🎭 Mango Madness Summer Show Through July 30
🛍️ Junk in the Trunk – June 20

🌟 This Week’s Highlights

🎟️ Summer Bingo Night

Wednesday, June 24 • Key West Theater • Free Entry • 6 pm

🧑‍🌾Farmer’s Market

Thursday, June 25 • Truman Waterfront Park • 1-6 pm

🤓Jackpot Trivia

Thursday, June 18 @ 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.

🖼️ Mango Madness Summer Art Show

The Studios of Key West
Celebrate the flavors, colors, and creativity of the Keys with this seasonal exhibition featuring local artists. Free to the public. Through July 30th.

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, June 22

• Rick Fusco @ Rams Head Southernmost — 5:30–8:30 PM
• Mary Spear @ The Gardens Hotel — 5–7 PM
• Colton Gleghorn @ Key West EmPOURium — 6–9 PM
• Charity Bingo @ Green Parrot Bar — 7–9 PM
• Martinis w/ Melodic Beats @ General Horseplay — 9 PM

Tuesday, June 23

• John Dion @ The Gardens Hotel — 5–7 PM
• Zack Seemiller @ Rams Head Southernmost — 5:30–8:30 PM
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Screaming Broccolli @ Sloppy Joe’s — 10 PM

Wednesday, June 24

• Jacin Waple @ Rams Head Southernmost — 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel — 5–7 PM
• A Pirate Looks Back: Jummy Buffett Tribute Show @ Comedy Key West — 12:30 PM
• Line Dancing @ Key West EmPOURium — 6:30–8:30 PM
• 3HG Band @ Sloppy Joe’s — 10 PM

Thursday, June 25

• Robert Douglas @ Rams Head Southernmost — 11 AM–2 PM
• Mac Calhoun @ Key West EmPOURium — 6–9 PM
• Chris Maloney @ Doc’s on Duval — 6–9 PM
• Hiram & Dan @ General Horseplay— 9 PM
• 3HG Band @ Sloppy Joe’s — 10 PM

Friday, June 26

• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• Reggae Lou & Kind Budz @ Key West EmPOURium — 5–8 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 6–9 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Follow the Rabbit @ Key West Theater — 7 PM & 9 PM
• 3HG Band @ Sloppy Joe’s — 10 PM

Saturday, June 27

• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 PM
• Jazz in the Garden with John Dion @ The Gardens Hotel — 5–7 PM
• Toko Irie @ The EmPOURium — 6–9 PM
• Jesse James Russell @ Doc’s on Duval — 6–9 PM
• Zach Lovering @ General Horseplay— 7 PM
• 3HD Band@ Sloppy Joe’s — 10 PM

Sunday, June 28

• Marjorie Lee @ Rams Head Southernmost — 11 AM–2 PM
• Pierce August @ Mac’s Place —4:30 PM–7:30 PM
• Jazz in the Garden with Belle Jampol @ The Gardens Hotel — 5–7 PM
• The Newtons @ Key West EmPOURium — 6–9 PM
• 3HD Band@ Sloppy Joe’s — 10 PM