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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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| | Spotlight Cabaret Series
featuring Laura Hodos - VIRTUAL CABARET
VIRTUAL DATES: February 13 - 16, 2026
Laura Hodos returns to The Winter Park Playhouse Spotlight Cabaret Series debuting her latest original solo cabaret, Old Friends. Join Laura for a stellar cabaret filled with iconic tunes and crowd-pleasing favorites, blending nostalgia, storytelling, and show-stopping vocals. Laura will wrap you in an evening of timeless songs that shape our lives featuring hits from celebrated artists such as Patsy Cline, Frank Sinatra, Stephen Sondheim, Billy Joel, Harry Chapin, Andrew Lloyd Webber, Ethel Merman and more!
Patrons will remember Ms. Hodos from her many performances at the Playhouse including Let's Face The Music, A Marvelous Party, Suds, Book of Merman and more! You may have also seen Laura in one of her previous 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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| | Spotlight Cabaret Series
featuring Rebecca Jo Lightfoot - LIVE
LIVE DATES:
February 18 & 19, 2026 @ 7:30pm
Rebecca Jo Lightfoot debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Rebecca Jo for an exciting evening of story and song.
Patrons will remember Mr. Lightfoot from her numerous performances at The Playhouse including Pump Boys and Dinettes, Heartbeats, and Honky Tonk Angels Holiday Hoedown 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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| | Motown - Pride of Motor City Featuring Greta Pope
Friday, February 27, 2025
7:30pm
A One-Night Only Special Event
Join internationally-acclaimed vocalist Greta Pope for a fabulously exciting look back at the legendary Motown artists. Hear all your favorites from the Motown Era, including Ike & Tina Turner, Marvin Gaye, The Supremes, The Tempations and many more!
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 Rebecca Jo Lightfoot - VIRTUAL CABARET
VIRTUAL DATES: Mar. 6 - 9, 2026
Rebecca Jo Lightfoot debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Rebecca Jo for an exciting evening of story and song.
Patrons will remember Mr. Lightfoot from her numerous performances at The Playhouse including Pump Boys and Dinettes, Heartbeats, and Honky Tonk Angels Holiday Hoedown 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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| | 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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| | Spotlight Cabaret Series
featuring Kevin Kelly - LIVE
LIVE DATES:
March 25 & 26, 2026 @ 7:30pm
Local Treasure Kevin Kelly debuts his latest solo cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Mr. Kelly will delight audiences with his cabaret evening full of standards! Cabaret audiences will love Kevin's renditions of classic songs from the collection of legendary performers and composers such as Tony Bennett, Duke Ellington, Frank Loesser, Johnny Mercer, Bobby Darin and Dean Martin.
Playhouse Patrons will remember Kevin from his numerous Playhouse cabarets and Mainstage performances including Murder For Two, Ruthless!, The Musical of Musicals and more! Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly so 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.
| Buy tickets |
| | Spotlight Cabaret Series
featuring Kevin Kelly - VIRTUAL CABARET
VIRTUAL DATES: Apr. 10 - 13, 2026
Local Treasure Kevin Kelly debuts his latest solo cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Mr. Kelly will delight audiences with his cabaret evening full of standards! Cabaret audiences will love Kevin's renditions of classic songs from the collection of legendary performers and composers such as Tony Bennett, Duke Ellington, Frank Loesser, Johnny Mercer, Bobby Darin and Dean Martin.
Playhouse Patrons will remember Kevin from his numerous Playhouse cabarets and Mainstage performances including Murder For Two, Ruthless!, The Musical of Musicals and more! Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly so 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.
| Buy tickets |
| | Spotlight Cabaret Series
featuring Tonya Phillips Staples - LIVE
LIVE DATES:
April 22 & 23, 2026 @ 7:30pm
Tonya Phillips Staples debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Tonya for an exciting evening of story and song.
Patrons will remember Ms. Staples from her Playhouse debut in The Bikinis. She also appeared in Sounds of the World, a Playhouse collaboration with Barbara Chandler Productions. 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.
| Buy tickets |
| | Spotlight Cabaret Series
featuring Tonya Phillips Staples - VIRTUAL CABARET
VIRTUAL DATES: May 8 - 11, 2026
Tonya Phillips Staples debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Tonya for an exciting evening of story and song.
Patrons will remember Ms. Staples from her Playhouse debut in The Bikinis. She also appeared in Sounds of the World, a Playhouse collaboration with Barbara Chandler Productions. 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.
| Buy tickets |