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| | Honky Tonk Angels Holiday Hoedown
November 14 - 23 & December 4 - 20, 2025
Previews: Nov. 13 at 7:30pm & Nov. 14 at 2:00pm
Written by Ted Swindley
The performances of Honky Tonk Angels Holiday Hoedown will take place in the Mandell Theater at Orlando Shakes located at 812 E. Rollins Street, Orlando, FL 32803.
Regional Premiere! This upbeat musical comedy continues the escapades of four beloved good 'ole country gals, The Honky Tonk Angels, as they reunite for a show at the Hillbilly Heaven Club in Nashville. With the holiday spirit in full force and a little bit of charming family drama, this joyful musical is full of popular holiday classics, a Motown Christmas medley, country hits like Dolly Parton's "Coat of Many Colors," fun comedy hits like "Grandma Got Run Over by a Reindeer" and much more!
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
NO LATE SEATING.
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| | Spotlight Cabaret Series
featuring Adam Biner
LIVE DATES:
November 19 & 20, 2025 @ 7:30pm
Adam Biner returns to The Winter Park Playhouse Spotlight Cabaret Series with his latest solo cabaret. Join Adam for an exciting evening of story and song.
Patrons will remember Mr. Biner from his star turn in The Playhouse's production of George M. Cohan Tonight! You may have also seen him in Five Course Love, What a Glorious Feeling, and Wreck the Halls to name a few. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for seating.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Spotlight Cabaret Series
featuring Adam Biner - VIRTUAL CABARET
VIRTUAL DATES: Dec. 5 - Dec. 8, 2025
Adam Biner returns to The Winter Park Playhouse Spotlight Cabaret Series with his latest solo cabaret. Join Adam for an exciting evening of story and song.
Patrons will remember Mr. Biner from his star turn in The Playhouse's production of George M. Cohan Tonight! You may have also seen him in Five Course Love, What a Glorious Feeling, and Wreck the Halls to name a few. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Spotlight Cabaret Series
featuring Carol Stein
LIVE DATES:
December 10 & 11, 2025 @ 7:30pm
The incomparable Carol Stein returns to The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Carol for an exciting evening of story and song.
Patrons may know Carol from her local performances at the theme parks, local jazz clubs and cabarets. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for seating.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Sinatra & Friends
Tuesday, December 16, 2025
7:30pm
A One-Night Only Special Event
As part of the One-Night-Only Series, The Playhouse will present a trip back to the Rat Pack Era with Sinatra & Friends. Mark Raisch returns to The Playhouse stage to celebrate the legendary crooners including Dean Martin, Tony Bennett, Bing Crosby and ol' blue eyes himself!
Net proceeds from the evening will benefit The Playhouse's quality musical programming. Tickets are only $65. Get yours before we sell out!
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| | Spotlight Cabaret Series
featuring Carol Stein - VIRTUAL CABARET
VIRTUAL DATES: Dec. 26 - Sep. 29, 2025
The incomparable Carol Stein returns to The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Carol for an exciting evening of story and song.
Patrons may know Carol from her local performances at the theme parks, local jazz clubs and cabarets. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | From My Hometown
A Celebration of the American Dream in Classic R&B
January 23 - February 21, 2026
Previews: Jan. 22 at 7:30pm & Jan. 23 at 2:00pm
Conceived by Lee Summers / Book by Lee Summers, Ty Stephens, and Herbert Rawlings, Jr.
The performances of From My Hometown will take place in the Mandell Theater at Orlando Shakes located at 812 E. Rollins Street, Orlando, FL 32803.
Southeastern Regional Premiere! This critically-acclaimed Off-Broadway musical is a "rags to riches" tale of three young men just off the bus from three hit-record producing hometowns - Philly, Memphis, and Detroit - as they meet at the world famous Apollo Theatre. The musical is a tantalizing homage to the 3-man R&B groups of the 60's and 70's and features twenty-four Rhythm and Blues classic soul songs made popular by artists such as James Brown, Ottis Redding, Jackie Wilson and more!
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
NO LATE SEATING.
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| | The Pin Up Girls
March 20 - March 29 & April 9 - 25, 2026
Previews: Mar. 19 at 7:30pm & Mar. 20 at 2:00pm
By James Hindman and Jeffrey Lodin
The performances of The Pin-Up Girls will take place in the Mandell Theater at Orlando Shakes located at 812 E. Rollins Street, Orlando, FL 32803.
Regional Premiere! From The Andrew Sisters to Hip-Hop and Gershwin to Beyoncé, The Pin-Up Girls sing a cavalcade of hits inspired by letters home from our troops overseas! While singing at the local VFW hall, the ladies stumble upon a huge stash of letters that date back 100 years. Inspired by what they find - funny, sexy, romantic and poignant - they put on a show that celebrates the men and woman who fight to defend out country.
"The show is a wonderful piece of entertainment. Memorable music, comedic characters and excellent performances." -Broadway World
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
NO LATE SEATING.
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