December 2 – 17, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse's holiday show turns the theatre into a 1940s radio studio for It's a Wonderful Life: […]
December 8, 2026 – January 2, 2027 · Shows at 7:00pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn opens its holiday slot with Shooting Star, a two-hander […]
January 7 – 9, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with Blanche and Beyond, Steve Lawson's one-man play assembled from Tennessee Williams's own letters. […]
Monday, January 18, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre America's premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo […]
January 19 – February 20, 2027 · Tuesdays–Saturdays at 7:30pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn follows its holiday show with Dracula: A Comedy of Terrors, […]
Thursday, January 21, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre One of Italy's most inventive performing arts companies makes a stop in Key West this January. NoGravity was […]
January 28 – February 6, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront's mainstage returns to Paul Slade Smith, whose The Angel Next Door played there previously, with […]
Monday, February 1, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre The New York Gilbert & Sullivan Players bring their production of to Key West this February. NYGASP has […]
Tuesday, February 9, 2027 Doors 5:30pm, Show 6:30pm · Tennessee Williams Theatre Afrique en Cirque comes to Key West as part of the Tennessee Williams Theatre's new Family Fun Series, […]
February 11 – 13, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with the Florida premiere of Call Me Elizabeth, written and performed by Kayla Boye. […]
Saturday, February 27, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre Ailey II is the junior company of Alvin Ailey American Dance Theater, and calling it a training ensemble […]
March 2 – 20, 2027 · Tuesdays–Saturdays at 7:30pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn stages Bess Wohl's Liberation, winner of the 2026 Pulitzer Prize for […]
