As part of its popular One-Night-Only Series, The Winter Park Playhouse will present the celebrated singing duo, Natalie Cordone and Shawn Kilgore, in their unique tribute, Stage to Screen.
The Winter Park Playhouse is a professional musical theatre affiliated with Actors' Equity Association and The National Alliance For Musical Theatre. This well respected 23 year old cultural gem sits in the heart of Winter Park Florida and features a Mainstage Season of Off-Broadway shows and Regional Premieres. Additionally, there is a monthly Spotlight Cabaret Series where proceeds in part go back directly to the artist.
Pianist and vocalist Carol Stein will perform her new holiday cabaret CAROL’S CAROLS as part of the Winter Park Playhouse Spotlight Cabaret Series on December 10 and 11, 2025.
The Winter Park Playhouse will present Sinatra and Friends, a dynamic 90-minute concert featuring the acclaimed Mark Raisch and his band The Martinis, for one night only on Tuesday, December 16, 2025, at 7:30 p.m.
Acclaimed triple-threat performer Adam Biner will return to The Winter Park Playhouse with his new solo cabaret, Back to the Basics, on Wednesday, November 19 and Thursday, November 20 at 7:30 p.m. as part of the theatre’s popular Spotlight Cabaret Series.
After months of anticipation and negotiation, The Winter Park Playhouse has secured a long-term home in Winter Park after the City of Winter Park purchased the venerable building with Orange County Tourism Development Tax (TDT) grant funds.
The Winter Park Playhouse will welcome acclaimed performer Desiree Montes in her new solo cabaret Sounds of Desiree: Reprisin’ and Manifestin’ on Wednesday, October 15, and Thursday, October 16, 2025, as part of the Spotlight Cabaret Series.
The multi-skilled Ms. Desiree Montes will take to the cabaret stage at The Winter Park Playhouse in her new solo cabaret - Sounds of Desiree: Reprisin' and Manisfestin'.
Broadway veteran Mr. John Cavazos brings his powerhouse vocals and captivating story to the Winter Park Playhouse stage in his original solo cabaret - My Broadway Footlights - held in The Mandell Theater at Orlando Shakes, September 17 and 18, 2025.
Ms. Desiree Montes will take to the cabaret stage at The Winter Park Playhouse in her new solo cabaret - Sounds of Desiree: Reprisin' and Manisfestin'. Learn how to purchase tickets!
The multi-talented Mr. Russell Stephens will debut his brand-new solo cabaret - Leading Ladies: Legends of Stage and Screen - in the Spotlight Cabaret Series at The Winter Park Playhouse April 23 and 24, 2025.
Havisham, written and performed by Heather Alexander with direction and dramaturgy by Dominque Gerrard, offers a compelling backstory to one of literature's most enigmatic characters. This one-woman show opens with a ghoulish, macabre set that perfectly establishes the tone for this exploration of Miss Havisham from Dickens's Great Expectations.
Kevin Kelly takes to the cabaret stage at The Winter Park Playhouse in his latest solo cabaret, I've Heard That Song Before, on March 26 and 27, 2025 at 7:30p.m. Playhouse Music Director, Christopher Leavy, will accompany on piano.
The Winter Park Playhouse features professional vocalist Rachel Hope Ihasz on the cabaret stage to perform her debut solo cabaret - An Ode To The Classics - in the theatre's popular Spotlight Cabaret Series, February 26 and 27, 2025. Playhouse Music Director, Christopher Leavy, will accompany on piano.
Todd Allen Long, takes to the cabaret stage at the theatre to perform his solo cabaret - Onstage and Backstage - in the Spotlight Cabaret Series, January 29 and 30, 2025.
Orange County Mayor and Commissioners awarded the City of Winter Park, in collaboration with The Winter Park Playhouse, 8 millions dollars to purchase the theatre's existing building and renovate the space, giving the beloved theatre a permanent home for decades to come.
Monica Titus brings her new cabaret, BEHIND THE SEAMS, to Winter Park Playhouse on November 20 and 21, 2024, as part of the Spotlight Cabaret Series.
Laura Hodos returns to the cabaret stage at The Winter Park Playhouse on October 16 and 17, 2024 to premiere her latest solo cabaret - Bewitched! Love and Other Enchantments - in the theatre's popular Spotlight Cabaret Series. Playhouse Music Director Christopher Leavy will accompany on piano.
Darryl Reuben Hall, a celebrated Broadway artist, will perform a solo cabaret show at The Winter Park Playhouse Spotlight Cabaret Series on September 25 and 26, 2024. Don't miss this special event.
Sahid Pabon will debut his solo cabaret at The Winter Park Playhouse Spotlight Cabaret Series on August 21 and 22, 2024.
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