Events

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  • Concerts
  • Performances
  • Screenings
  • Special Events
  • Talks
MONDAYS & TUESDAYS, 5-7PM
2025 | HAPPY HOUR

Glow Hours on Hugh’s View

Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight.

SORRY THIS SHOW HAS BEEN CANCELED
2026 | CONCERT

Best of Barsha

Singer, songwriter, and musical chameleon Debra Barsha takes the stage for an intimate evening of bold grooves and storytelling.

FRI JAN 30 & SAT JAN 31, 8PM
2026 | FIRST LOOK

First Look: The Starters

Emily is counting down the days until her husband Matt can retire from his all-consuming, backbreaking, high-stress job: playing in the NFL. But Matt is clinging to the game and won’t let go.

FEB 3, 7PM & FEB 4, 6PM
2026 | CONCERT

John McCutcheon in Concert

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

FRI & SAT FEB 6-7, 7PM
2026 | SCREENING

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.

MON FEB 9, 6PM
2026 | CONCERT

Irie Monte, Michelle Sanchez, and Zach Brown in Concert

From the rhythmic drive of Bartók’s Romanian Folk Dances to beloved melodies by Dvořák, and John Hartford, this program celebrates how folk music continues to inspire composers across oceans and generations.

WED FEB 11, 6PM
2026 | CONCERT

Libby York: Our Love is Here to Stay

Vocalist Libby York and her quartet, featuring Chicago pianist Tom Vaitsas, celebrate classic love songs from the Great American Songbook and beyond in a jazz Valentine at Hugh’s View!

FRI FEB 13 & SAT FEB 14, 8PM
2026 | FIRST LOOK

First Look: The Patrons

In 1963, a new librarian secretly checks out a controversial book to a teenager. Local tempers flare against the library as the staff must choose how far they will go to protect their ideals and each other.

MON FEB 16, 8PM
2026 | SPOTLIGHT CABARET

Billy Stritch and Gabrielle Stravelli

Renowned pianist/singer and award-winning jazz vocalist combine their considerable talents for an evening of great music celebrating the legendary Mel Tormé and Ella Fitzgerald.

FEB 17, 7PM & FEB 18, 6PM
2026 | CONCERT

Rachael Sage in Concert

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

FRI FEB 20, 7PM
2026 | CONCERT

Darcy Cooke: Songs & Stories of the Silver Screen

Step into Hollywood’s golden age with singer Darcy Cooke as she revisits the music that made the movies shine.

SUN FEB 22, 5PM
2026 | CONCERT

The Music Room Youth Classical Concert

Talented young musicians from The Music Room take center stage in this inspiring evening of classical performance. Directed by Robin Kaplan, the concert showcases the next generation of performers.

MON FEB 23, 5PM
2026 | TALK

Between Two Palms with Roxana Saberi

Roxana Saberi is an award-winning journalist, author, and former CBS News correspondent. Saberi, whose reporting spans global conflict zones and major human rights stories, will speak about the courage, clarity, and ethical responsibility.

FRI FEB 27, 5PM
2026 | AUCTION

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.

SAT FEB 28, 11AM-3PM
2026 | EVENT

Artist Studio Tours

Peek behind the scenes of Key West’s vibrant art community during this self-guided tour of local studios.

MON MAR 2, 8PM
2026 | SPOTLIGHT CABARET

Max von Essen

Tony-nominated Broadway star Max von Essen brings his golden tenor and timeless showmanship to the Spotlight Cabaret for a night of music and charm.

MAR 3, 7PM & MAR 4, 7PM
2026 | CONCERT

Jon Langford in Concert

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

FRI MAR 6, 7PM
2026 | CONCERT

Cortadito in Concert

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

MAR 10, 7PM & MAR 11, 7PM
2026 | CONCERT

Jake Shimabukuro in Concert

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

FRI MAR 13, 6:30PM
2026 | CONCERT

Music Rendezvous with May Phang, PEAR

Pianist May Phang invites audiences on a luminous musical journey across cultures and centuries. Expect an intimate, thought-provoking evening of color, expression, and connection through music.

FRI MAR 20 & SAT MAR 21, 8PM
2026 | FIRST LOOK

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.

FRI APR 3 & SAT APR 4, 8PM
2026 | FIRST LOOK

First Look: My Maria

Chuck finds love through country line dancing, until a mass shooting exposes his weakness, sparking a gripping journey about the complexities of cowardice and the power of love.

MON MAR 23, 7PM
2026 | CONCERT

Zoë Lewis in Concert

With songs, stories, and multimedia magic, Lewis blends humor, heart, and high energy into a joyful reflection on memory, belonging, and the art of living fully.

MAR 24, 7PM & MAR 25, 7PM
2026 | CONCERT

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.

MON MAR 30, 8PM
2026 | SPOTLIGHT CABARET

Randy Roberts and Donna McKechnie

Broadway legend Donna McKechnie, Tony® Award winner for A Chorus Line, joins master entertainer Randy Roberts for an evening of music, stories, and legacy of Broadway’s golden era for a night of pure theatrical joy.

WED & THU APR 8 & 9, 7PM
2026 | EVENT

Performances by Mike Wiley

Acclaimed actor and playwright Mike Wiley returns to Key West with two new one-man performances honoring pivotal figures in Black history.