Events

Illustration of a woman with wide green eyes and dark hair holding a phone tightly, looking anxious or shocked, against a purple gradient background.

January 1, 1970 - January 1, 1970

First Look: Mom’s Best Friend

When June’s adult daughter—once her best friend—suddenly cuts ties, a woman is forced to confront the truth about herself and her life.

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A four-piece Latin band stands against a peach-colored wall, featuring a double bassist, percussionist with congas, and two guitarists, all smiling and ready to perform.

January 1, 1970 - January 1, 1970

Cortadito in Concert

Hailing from Miami, Cortadito revives the soulful rhythms of Son Cubano—the sound that inspired the Buena Vista Social Club.

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Logo graphic reading “Riff on RoxFilm – Roxbury International Film Festival” in bold black and red text.

January 1, 1970 - January 1, 1970

Riff on RoxFilm

The Roxbury International Film Festival returns to Key West for a three-day celebration of films by, for, and about people of color. Featuring screenings, talkbacks, and meet-and-greets with filmmakers.

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Writer and speaker Danny Rubin gestures expressively with both hands while sitting on a director’s chair, wearing glasses and a dark pullover over a red shirt.

January 1, 1970 - January 1, 1970

Between Two Palms with Danny Rubin

Danny Rubin is an acclaimed American screenwriter and playwright best known for writing the story, and co-writing the screenplay for the iconic film Groundhog Day.

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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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