DEAD FEST KEY WEST – April 17, 18, 19 – 2026
Join us for DEAD FEST KEY WEST 2026, a thrilling free festival celebrating the Grateful Dead's legacy. Headlined by the electrifying STEELY DEAD, the event…
Free
69 events found.
Events for April 19, 2026
Ongoing
DJ Marty at Red Garter Saloon Stage
DJ Marty is a dynamic and innovative music curator renowned for his electrifying performances at the Red Garter Saloon Stage. His seamless mixing skills and…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs Stage. A Key West icon, DJ Chaka infuses his sets with energy and passion,…
Free
The Tiki Bombs at Tiki House Key West
The Tiki Bombs are a dynamic band renowned for their electrifying performances and tropical-inspired sound. Merging traditional island melodies with modern rock, they deliver a…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying performances of The Durtbags at Durty Harry's Stage in Key West's Rick's Entertainment Complex. Known as the ultimate party rock band, they…
Free
Karaoke at Bobby’s Monkey Bar
Experience a night of vibrant entertainment at Bobby's Monkey Bar in Key West's Old Town, where the star of the show is the charismatic karaoke…
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar in Key West. Known for their bold stage presence and dynamic sound, this edgy…
Free
Jack Wolf at Irish Kevin’s Bar
Jack Wolf, a talented singer-songwriter based in Key West, captivates audiences at Irish Kevin's Bar with his soulful performances. Known for his passionate melodies and…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Experience an unforgettable evening with DJ Jason at Rick's Bar Downstairs Stage in Key West. Known for his electrifying beats and ability to read the…
Free
Tunaskin Island Clean Up | Key West
Experience the vibrant energy of the Tunaskin Island Clean Up in Key West on April 19th. After joining fellow volunteers to help beautify the island,…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a daily party boat fishing experience at A & B Marina in Key West's historic seaport. Enjoy live entertainment amidst the…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Yoga on the Beach at Fort Zachary Taylor in Key West provides a serene setting with historic charm and stunning ocean views. The real highlight…
$20
Chris at Two Friends Patio Restaurant
Join Chris at Two Friends Patio Restaurant for an unforgettable evening in Key West. Enjoy the lively ambiance of Duval Street while Chris fills the…
Free
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh captivates audiences at Sloppy Joe's Bar with her vibrant musical performances. Based in the Florida Keys, she delivers feel-good covers, creative mashups, and…
Free
Key West Artisan Market at Higgs Beach
The Key West Artisan Market at Higgs Beach offers a vibrant atmosphere with the highlight being live entertainment. Visitors can enjoy performances amid the picturesque…
KW ARTISAN MARKET – EARTH DAY EDITION
Experience the KW Artisan Market Earth Day Edition at Higgs Beach, a vibrant celebration featuring local artists and specialty foods. The highlight is the live…
Free
Marjory Lee at Rams Head Southernmost
Marjory Lee, a captivating musician from Key West, enchants audiences with her soulful voice and expert guitar skills at Rams Head Southernmost. As the Fantasy…
Free
Cow Key Bridge Run – Key West Zero K! | Cowless In Wonderland
The Cow Key Bridge Run - Key West Zero K! is an eccentric spectacle featuring the vibrant Conch Republic Cowntina Moo-sers Party. Enjoy dazzling performances,…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings dynamic performances to Irish Kevin's Bar, captivating audiences with his musical talent. Known for his engaging style, Bradd creates an unforgettable atmosphere…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum group of four. The entertainer, a spirited mixologist, will guide you through…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant Key West Legal Rum Distillery with daily free tours and tastings. Although there’s no specific entertainer mentioned, the lively setting itself offers…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise for a unique maritime experience in Key West. While the tour offers breathtaking views of vibrant marine life through…
$69.95
Cow Key Bridge ZERO-K Run
The Cow Key Bridge ZERO-K Run on April 19, 2026, promises a whimsical Cowless in Wonderland theme in Key West. This family-friendly event is a…
Free
COW KEY CHANNEL BRIDGE ZERO-K
COW KEY CHANNEL BRIDGE ZERO-K features a charming Zero K run across the Cow Key Bridge in Key West. While details about a specific entertainer…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco captivates audiences at Two Friends Patio Restaurant with his mesmerizing musical performances. His talent enhances the vibrant atmosphere of this iconic Key West…
Free
Aaron Blumer at Hog’s Breath Saloon
Aaron Blumer captivates audiences at Hog's Breath Saloon with his free-spirited, adventurous nature. Known for his spontaneous performances, Blumer seamlessly blends exploration with music, leaving…
Free
Harley Ray at Rick’s Downstairs Stage
Experience the captivating artistry of Harley Ray at Rick's Downstairs Stage. Known for his passionate and innovative songwriting, Ray delivers melodies and lyrics that deeply…
Free
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a vibrant Louisiana native, enchants audiences at Sloppy Joe's Bar with his spirited tales and blues harmonica skills. This local legend…
Free
Mylo O’Maolain at Schooner Wharf Bar
Mylo O'Maolain, an enchanting Irish-born musician, lights up Schooner Wharf Bar in Key West with his dynamic performances. Fusing Irish traditions with modern flair, his…
Free
Mike Emerson Jazz Quartet at Green Parrot Bar
Experience the dynamic rhythms of the Mike Emerson Jazz Quartet at Green Parrot Bar, where exceptional jazz talents come alive. Known for their captivating performances,…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the vibrant marine life of Key West aboard the Glass Bottom Boat Cruise, featuring captivating performances by talented local entertainers. This unique excursion combines…
$69.95
Jeff Harris at Irish Kevin’s Bar
Experience the vibrant performances of Jeff Harris at Irish Kevin's Bar in Key West. An acclaimed singer, songwriter, and comedian, Jeff captivates audiences with his…
Free
Aaron Hudgins at Tiki House Key West
Experience the captivating performances of musician Aaron Hudgins at Tiki House Key West. Known for his engaging live music, Aaron brings vibrant energy to the…
Free
Mike Emerson Jazz Quartet at Green Parrot Bar
The Mike Emerson Jazz Quartet captivates audiences at Green Parrot Bar with their dynamic and soulful performances. Known for his remarkable improvisation and vibrant stage…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the vibrant Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West's Historic Seaport. Dive into an adventure with…
$79.95
Tea Dance at La Te Da
Experience an unforgettable evening at the Tea Dance at La Te Da in Key West. Enjoy the captivating performances of talented drag queen Randy Roberts,…
Free
Dave Minninberg at Mac’s Place
Dave Minninberg brings his captivating performance to Mac's Place, a lively waterfront sports bar in Key West. Known for his engaging stage presence and musical…
Free
Dead Fest Key West at The Alamo Key West
Dead Fest Key West at The Alamo showcases electrifying live performances in a lively outdoor setting. As a prominent entertainer takes the stage, attendees can…
Free
Happy Dog at The Alamo Key West
Experience the electrifying performance of Happy Dog Band at The Alamo Key West. This improvisational jam band captures the essence of the psychedelic era, inviting…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West, where the ocean comes alive beneath your feet. Marvel at the vibrant marine life through…
$69.95
Trenton Chandler at Rick’s Bar Downstairs Stage
Trenton Chandler, a country musician hailing from Shallowater, Texas, brings the essence of West Texas to life on Rick's Bar Downstairs Stage. Influenced by legends…
Free
801 Karaoke – Hosted by Jeff
Join the lively atmosphere at 801 Bourbon Bar's Karaoke night hosted by the charismatic Jeff. Nestled in Old Town Key West, Jeff's dynamic energy makes…
Free
Ross Brown Duo at Hog’s Breath Saloon
Experience the captivating performance of the Ross Brown Duo at Hog's Breath Saloon. Based in Key West, Ross Brown is a versatile musician whose dynamic…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls deliver an electrifying 5pm drag show at the iconic 801 Bourbon Bar in Key West. Known for their charismatic performances…
QMitch Drag Queen Bingo at 22&Co
Experience the vibrant world of QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Known for unforgettable performances, QMitch dazzles with charisma and…
Free
Sunday Jazz at the Gardens
Experience the enchanting Sunday Jazz at the Gardens, where the spotlight shines on renowned jazz performers amidst the lush, tropical backdrop of The Gardens Hotel.…
Free
JAZZ IN THE GARDENS
Jazz in the Gardens at The Gardens Hotel features world-renowned jazz artists set in a captivating tropical garden environment. Guests can enjoy live performances while…
Free
Rick Fusco at Rams Head Southernmost
Rick Fusco, a talented musician, captivates audiences at Rams Head Southernmost with his engaging performances. Known for his dynamic presence and soulful tunes, Fusco creates…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West enchants audiences at El Meson de Pepe's on Mallory Square. Known for their captivating live performances, Caribe infuses the vibrant Cuban…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West, where the famous cat man and other street performers captivate audiences against a stunning…
Free
Shanty Hounds at Two Friends Patio Restaurant
Shanty Hounds, an inventive acoustic duo featuring Dani Hoy and Key West Chris Rehm, brings lively performances to Two Friends Patio Restaurant. Based in Key…
Free
The Heavy Pets Soundcheck Set at Green Parrot Bar
The Heavy Pets deliver an electrifying performance at the Green Parrot Bar, captivating the audience with their dynamic sound and infectious energy. Known for their…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Pete & Larry Sloppy 2nds are a dynamic musical duo captivating audiences at Sloppy Joe's Bar in Key West. With their eclectic style, they blend…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
CONCH DELIGHT CULTURAL DINNER UNER THE STARS
Experience a delightful evening at Grimal Grove's Conch Delight Cultural Dinner Under the Stars. Savor exquisite Cuban, Bahamian, and Caribbean dishes crafted by French-trained chef…
Free
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room, featuring an engaging entertainer who will take you on a nostalgic…
Free
Jesse & Jillian at Schooner Wharf Bar
Join the dynamic duo Jesse & Jillian, also known as The Happy Dog, at Schooner Wharf Bar for an unforgettable evening of music and laughter.…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage in Key West's Rick's Entertainment Complex. Renowned for his seamless mixing and…
Free
Jack Wolf at Halo Rooftop Lounge Bar at The Saint
Experience the soulful sounds of Jack Wolf at Halo Rooftop Lounge Bar at The Saint. A gifted singer-songwriter based in Key West, Jack enchants audiences…
Free
Ronnie Lovely at La Te Da
Experience the vibrant talent of Ronnie Lovely at La Te Da in Key West. Known for their captivating performances, Ronnie brings a unique flair to…
Free
Steely Dead at The Alamo Key West
Steely Dead brings a dynamic fusion of rock and blues-inspired performances to The Alamo Key West. Known for their captivating live shows, this talented band…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where this legendary magician captivates audiences with his innovative illusions and captivating storytelling. Renowned…
Free
Elle Haley at Tiki House Key West
Experience the vibrant musical talent of Elle Haley at Tiki House Key West. A dynamic musician from the Florida Keys, Elle captivates audiences with her…
Free
Aaron Hudgins at Rick’s Bar Downstairs Stage
Experience the captivating performance of Aaron Hudgins at Rick's Bar Downstairs Stage. Known for his dynamic presence and musical talent, Aaron delivers an unforgettable live…
Free
Homegrown at Hog’s Breath Saloon
Homegrown is a dynamic country band from Key West, celebrated for their heartfelt lyrics and captivating melodies. Performing at Hog's Breath Saloon, they offer a…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable evening at Bobby's Monkey Bar with dynamic karaoke sessions led by an engaging and talented entertainer. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the charismatic Mylo O'Maolain captivating audiences at Irish Kevin's Bar in Key West. Known for his vibrant performances, Mylo brings infectious energy and musical…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar, where this edgy party rock band delivers high-octane performances that captivate audiences. Known for…
Free