Events

January 1, 1970 - January 1, 1970

December Duo Holiday Concert

Irie Monte will be joined by Crispin Campbell on cello for an evening of beautiful string music on the rooftop. Let the music get you into the holiday spirit!

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Playful illustrated graphic featuring a cartoon-style dog with its tongue out, surrounded by colorful bingo balls spelling “B-I-N-G-O.” The text reads “Bingo is my name-o.” In the corner, the Green Parrot Bar logo appears, promoting the Key West venue’s bingo event.

January 1, 1970 - January 1, 1970

Bingo at the Green Parrot

Join Gwen Filosa for the island’s favorite Monday-night tradition! Grab a drink, snag your cards, and play for prizes ranging from local art to bar tabs.

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Oil painting by Joanne Sloan depicting a tranquil seascape in soft blues, purples, and aquamarine tones. Billowing clouds fill the sky above calm turquoise water, with a faint silhouette of a distant lighthouse on the horizon. Created for the Anne McKee Art Auction.

January 1, 1970 - January 1, 1970

Anne McKee Artists Fund Fine Arts Auction

Come celebrate vintage Key West in our tropical piano bar featuring entertainment by Bobby Nesbitt and artworks by 40 local artists featured in the live auction.

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Ricky Skaggs and Sharon White smile warmly outdoors, each holding their instruments — Skaggs with his mandolin, White with her guitar. Sunlight filters through the trees behind them, capturing the warmth, harmony, and enduring partnership that define their decades-long musical and personal journey.

January 1, 1970 - January 1, 1970

Ricky Skaggs and Sharon White in Concert

Bluegrass legends Ricky Skaggs and Sharon White unite for an unforgettable night of harmony, heart, and timeless tradition.

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Ukulele virtuoso Jake Shimabukuro stands against a vivid red wall, strumming his instrument with a relaxed smile. Dressed in a black leather jacket and dark shirt, he radiates calm confidence and creative energy, embodying the boundary-breaking spirit that has made him one of the world’s most celebrated ukulele players.

January 1, 1970 - January 1, 1970

Jake Shimabukuro in Concert

Ukulele virtuoso Shimabukuro pushes musical boundaries with dazzling skill, heart, and fearless creativity.

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Musician and artist Jon Langford stands before a brick wall decorated with his own artwork, holding an acoustic guitar mid-strum. His serious expression contrasts with the vivid, folk-inspired imagery behind him, capturing the creative fusion of punk energy and Americana roots that defines his work.

January 1, 1970 - January 1, 1970

Jon Langford in Concert

Punk pioneer and visual artist Langford blends country, folk, and rebellion in a fearless, genre-bending performance.

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Singer-songwriter Rachael Sage poses against a colorful, abstract backdrop. She wears bright, patterned clothing, turquoise earrings, and flowers in her hair, radiating creativity and joyful energy.

January 1, 1970 - January 1, 1970

Rachael Sage in Concert

Folk-pop visionary Sage blends wit, warmth, and resilience in luminous songs that inspire and uplift.

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Folk musician John McCutcheon smiles warmly while holding a banjo across his chest. He wears a striped shirt and dark vest, standing before a wooden backdrop that evokes the roots and warmth of traditional folk music.

January 1, 1970 - January 1, 1970

John McCutcheon in Concert

Folk icon McCutcheon presents dazzling musicianship, heartfelt songs, and storytelling that bridges generations.

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Musician Susan Werner performs on stage, smiling as she sings into a microphone while playing a grand piano under warm stage lights.

January 1, 1970 - January 1, 1970

Susan Werner in Concert

Multi-instrumentalist with classical vocal training, Werner has built a reputation over more than 25 years as one of the most innovative songwriters working today.

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Festive holiday graphic with decorated Christmas tree branches and ornaments, featuring text “Eaton St Stroll – A Magical Holiday Event.”

January 1, 1970 - January 1, 1970

Eaton Street Christmas Stroll

Join Eaton Street for a magical holiday event featuring festive performances by local choirs, unique gifts and holiday hospitality! Soak up the island cheer in the heart of Old Town.

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