WOOF Week 2026!
Experience the excitement of WOOF Week 2026 in Key West, featuring sizzling daytime and nighttime parties. The highlight of the event is electrifying performances by…
Free
61 events found.
Events for April 22, 2026
Ongoing
DJ Todd at Red Garter Saloon Stage
DJ Todd, an innovative DJ known for his eclectic mixes and dynamic performances, commands the Red Garter Saloon Stage with his unique soundscapes. His energetic…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a dynamic music producer renowned for his mesmerizing mixes and electrifying performances. Known for blending genres with a vibrant stage presence, he…
Free
LUVBOM at Durty Harry’s Stage
Experience the electrifying energy of LUVBOM at Durty Harry's Stage in Key West. This dynamic performer captivates audiences with his vocal prowess and guitar skills.…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the Alex Anthony Band at Hog's Breath Saloon, where Alex Anthony redefines the cover band scene. Known for their electrifying performances and unique blend…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant evening of karaoke at Bobby's Monkey Bar in Key West's Old Town. This lively venue features talented local entertainers who bring excitement…
Radio Hero at Sloppy Joe’s Bar
Radio Hero energizes Sloppy Joe's Bar with their explosive and edgy party rock performances. Known for their dynamic sound and bold stage presence, this band…
Free
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf graces Irish Kevin's Bar with their captivating presence, blending diverse talents to create an unforgettable experience. Known for their charismatic charm and strategic…
Free
Karaoke w/ Jorge at Rick’s Bar Downstairs Stage
Join DJ Jorge for an electrifying karaoke night at Rick's Bar Downstairs Stage. Known for his vibrant performances and energetic beats, DJ Jorge keeps the…
Free
Earth Day with Reef Relief
Celebrate Earth Day with Reef Relief and the City of Key West at the White Street Pier. Enjoy a fun-filled day featuring KEEN Footwear, where…
Free
Yoga on the Beach – Ft Zachary Taylor
Join a rejuvenating Yoga on the Beach session at Fort Zachary Taylor State Park in Key West. While the serene setting offers historic charm and…
$20
Aqua Yoga at Southernmost Beach Resort
Aqua Yoga at Southernmost Beach Resort offers a serene experience led by an expert yoga instructor. Immerse yourself in tranquility as you practice yoga in…
$20
Earth Day Scavenger Hunt/Clean Up
Celebrate Earth Day with us at the Southernmost Beach Cafe Patio on South Beach. Enjoy live entertainment as you participate in a community Clean Up…
Free
Alfonse at Two Friends Patio Restaurant
Experience the vibrant sounds of Alfonse at Two Friends Patio Restaurant in Key West. Renowned for energizing live performances, Alfonse captivates audiences with his musical…
Free
Chris Thomas at Sloppy Joe’s Bar
Chris Thomas brings his exceptional musical talent to Sloppy Joe's Bar, captivating audiences with his vibrant energy and versatile performances. Known for his dynamic presence,…
Free
Barrett Thomas at Rams Head Southernmost
Barrett Thomas, a dynamic musician from Key West, brings innovative live performances to Rams Head Southernmost. Renowned for his skillful looping and captivating energy, Barrett…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak electrifies Irish Kevin's Bar with his dynamic performances, showcasing his unique sound and captivating charisma. A versatile musician and band leader, Oren delights…
Free
Wednesday Filet Day at Mary Ellen’s
Mary Ellen's Wednesday Filet Day is a must-visit in Old Town Key West, where the lively atmosphere pairs perfectly with live music from talented local…
Free
Michael Corleto at Rick’s Bar Downstairs Stage
Michael Corleto, a gifted singer-songwriter and multi-instrumentalist from Maine, captivates audiences at Rick's Bar Downstairs Stage with his heartfelt lyrics and rich melodies. His dynamic…
Free
Andy Mauerman at Hog’s Breath Saloon
Andy Mauerman, a musician known for his advocacy of experiential living and personal growth, brings his soulful performance to Hog's Breath Saloon. With a focus…
Free
Andy Westcott at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Andy Westcott captivates audiences with his unique sound and engaging performances. Based in Key West, this talented musician is building anticipation…
Free
Tony Baltimore at Schooner Wharf Bar
Experience the musical artistry of Tony Baltimore at Schooner Wharf Bar in Key West. This talented singer/songwriter blends alternative roots-rock with captivating originality. Raised by…
Free
Community Blood Drive
Join the Community Blood Drive at Key Plaza, featuring lively entertainment by the Conch Republic Aerospace Program (****.). Enjoy great music and a spirited atmosphere…
Free
Sharese Nicole at Tiki House Key West
Sharese Nicole, a gifted singer-songwriter, graces Tiki House Key West with her soulful performances. With Mississippi and Key West roots, she brings heartfelt music and…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings his vibrant musical talent to Irish Kevin's Bar, an iconic live music venue in Old Town Key West. Known for engaging audiences…
Free
Nina Newton at Two Friends Patio Restaurant
Enjoy a captivating evening with Nina Newton at Two Friends Patio Restaurant. Born and raised in Key West, Nina is a talented singer-songwriter known for…
Free
Harley Ray at Rick’s Bar Downstairs Stage
Experience the unforgettable artistry of Harley Ray at Rick's Bar Downstairs Stage. A passionate and innovative songwriter, Ray captivates audiences with authentic melodies and lyrics…
Free
Nick Norman at Mac’s Place
Experience the soulful sounds of Nick Norman at Mac's Place in Key West. A talented singer-songwriter from South Carolina, Nick captivates audiences with his heartfelt…
Free
Harley Ray at Hog’s Breath Saloon
Harley Ray captivates the audience at Hog's Breath Saloon with his authentic and emotionally rich performances. As a passionate songwriter, he crafts melodies and lyrics…
Free
World Famous 801 Girls- 5pm Show
Experience the vibrant energy of the World Famous 801 Girls at their 5pm show in Old Town Key West's iconic 801 Bourbon Bar. These talented…
Jay Bangles at Tiki House Key West
Experience the vibrant performances of Jay Bangles at Tiki House Key West. As co-owner and talented musician, Jay infuses the lively venue with his unique…
Free
John Sausser at Rams Head Southernmost
Experience an unforgettable evening with John Sausser at Rams Head Southernmost. Known for his captivating performances, Sausser brings energy and passion to every show. Enjoy…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainment takes center stage. Revel in the captivating performances of street entertainers like jugglers and the…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned Cuban restaurant enchants guests with live…
Claire Finley and Dave Scher at Green Parrot Bar
Claire Finley and Dave Scher captivate audiences with their dynamic performances at the renowned Green Parrot Bar in Key West. Known for their engaging stage…
Free
Marjory & Sid at Sloppy Joe’s Bar
Experience the soulful sounds of Marjory Lee at Sloppy Joe's Bar, a historic Key West landmark. A masterful guitarist and Fantasy Fest Queen 2024, Marjory…
Free
Bria Live at Bel Mare
Experience the enchanting performance of Bria Live at Bel Mare. Her smooth, soulful sound captivates audiences, perfectly complementing the venue's waterfront views and ambiance. Enjoy…
Free
Charlie Knott & Friends at The Alamo Key West
Charlie Knott, a dynamic songwriter, guitarist, and singer, captivates audiences with his charismatic and rebellious spirit. Known for his multifaceted artistry and intriguing persona, Charlie…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a beloved entertainer at Irish Kevin's Bar in Key West, captivates with his charm and humor. Known for his genuine spirit and engaging…
Free
HOT HAVANA NIGHT DANCE PARTY & SILENT AUCTION
Immerse yourself in the vibrant rhythms of HOT HAVANA NIGHT DANCE PARTY at Kaya Island Eats. Featuring electrifying performances, salsa the night away while enjoying…
Free
Line Dancing at Kaya Island Eats
Kick up your heels at Kaya Island Eats for an unforgettable evening of line dancing. Nestled in Key West, this laid-back venue blends Caribbean culinary…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating performance of Ericson Holt at Two Friends Patio Restaurant in Key West. Known for his soulful melodies and engaging stage presence, Holt…
Free
Arts & Drafts at The Retro Room
Arts & Drafts at The Retro Room showcases an exceptional entertainer, creating a vibrant atmosphere in this nostalgic café and game room. Located in Old…
Free
Jefff Clark at Schooner Wharf Bar
Experience the vibrant talent of Jefff Clark at the Schooner Wharf Bar in Key West. A budding music artist, Jefff captivates audiences with his innovative…
Free
Andrew B. at Rick’s Bar Downstairs Stage
Andrew Burleson lights up Rick's Bar Downstairs Stage with his engaging melodies and charismatic personality. Known for blending humor with his musical talents, Andrew charms…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where the legendary magician captivates audiences with his innovative illusions and compelling storytelling. Known…
Free
DJ Todd at Red Garter Saloon Stage
DJ Todd is an innovative and electrifying DJ renowned for his eclectic mixes and high-energy performances. Known for captivating audiences with his unique soundscapes and…
Free
Jay Bangles at Tiki House Key West
Jay Bangles, the co-owner and talented musician at Tiki House Key West, is renowned for his vibrant performances that ignite the lively atmosphere. His dedication…
Free
Ronnie & Gregory at La Te Da
Experience the captivating synergy of Ronnie and Gregory at La Te Da in Key West. This dynamic duo enchants audiences with their vibrant personalities and…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering, a vibrant musician from the Florida Keys, captivates audiences with his soulful melodies at Halo Rooftop Lounge Bar. Known for his unique blend…
Free
Earth Day Jam with That Hippie Collective
Join That Hippie Collective for an unforgettable Earth Day Jam at Key West Theater. This vibrant event celebrates Earth Day with three dynamic bands and…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a renowned music producer and DJ celebrated for his captivating mixes and electrifying performances. Known for blending genres seamlessly, he enthralls audiences…
Free
Claire Finley and Dave Scher at Green Parrot Bar
Claire Finley and Dave Scher bring their musical talent to the iconic Green Parrot Bar in Key West. Known for captivating performances, Finley and Scher…
Free
Tony V at Comedy Key West
Tony V, renowned for his wit and unique comedic style, was named the Funniest Person in Massachusetts in 1986. He has graced prestigious platforms like…
$35
Crank Sinatra at Durty Harry’s Stage
Experience the electric energy of Krank Sinatra at Durty Harry's Stage in Key West. This multi-talented musician captivates audiences with his powerful vocals and masterful…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Band at Hog's Breath Saloon. Known for transforming the modern cover band scene, Alex Anthony delivers unforgettable…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant night of music at Bobby's Monkey Bar in Key West's Old Town. Experience the lively island atmosphere as entertainers bring the karaoke…
Kari Wolf at Irish Kevin’s Bar
Kari Wolf, an electrifying musician from Key West, enthralls audiences at Irish Kevin's Bar with her soulful melodies and captivating performances. Her unique style creates…
Free
Radio Hero at Sloppy Joe’s Bar
Radio Hero is an electrifying party rock band performing at Sloppy Joe's Bar, known for their high-energy and dynamic sound. Their explosive performances blend rock…
Free
Claire Finley and Dave Scher at Green Parrot Bar
Claire Finley and Dave Scher light up the Green Parrot Bar with their engaging performances. Known for their dynamic chemistry and captivating musical talent, the…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join DJ Davis at Rick's Bar Downstairs Stage for an electrifying karaoke night. Known for his charismatic performances and diverse music selections, Davis brings infectious…
Free