This Week in Key West: June 15–21, 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 15–21, 2026.

🌟 This Week at a Glance

🌞 Summer Solstice Celebration – Through June 21
🎟️ 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 Solstice Celebration

June 8–21 • Mallory Square

Celebrate the longest days of the year at Key West’s iconic Sunset Celebration. Enjoy nightly street performers, local artists, food vendors, live entertainment, and breathtaking waterfront sunsets as the island welcomes the Summer Solstice.

🎟️ Summer Bingo Night

Wednesday, June 17 • Key West Theater • Free Entry • 6 pm

🎨 Walk on White

Thursday, June 18

Spend the evening exploring galleries, studios, and local businesses during one of Key West’s favorite monthly art walks. https://www.walkonwhitekeywest.com/

🤓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 Members 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.

🛍️ Junk in the Trunk Community Garage Sale

Saturday, June 20 • Truman Waterfront Park

Browse unique finds, local treasures, and one-of-a-kind bargains at this community favorite.

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 15

• Tony Roberts @ 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 16

• Zack Seemiller @ Rams Head Southernmost — 5:30–8:30 PM
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Mayday By Midnight @ Sloppy Joe’s — 10 PM

Wednesday, June 17

• Jacin Waple @ Rams Head Southernmost — 11 AM–2 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
• Screaming Broccolli @ Sloppy Joe’s — 10 PM

Thursday, June 18

• 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
• The Marshall Morlock Band: Summer Send Off @ Key West Theater— 8 PM
• Good Trees River Band @ General Horseplay— 9 PM

Friday, June 19

• 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
• Screaming Broccolli @ Sloppy Joe’s — 10 PM

Saturday, June 20

• 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
• Screaming Broccolli @ Sloppy Joe’s — 10 PM

Sunday, June 21

• 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 John Dion @ The Gardens Hotel — 5–7 PM
• The Newtons @ Key West EmPOURium — 6–9 PM
• Screaming Broccolli @ Sloppy Joe’s — 10 PM