My Shows
News on your favorite shows, specials & more!

WINTER PARK PLAYHOUSE

812 East Rollins Street Orlando FL 32803
Winter Park , FL 32789

Upcoming Shows

The Pin-Up Girls
The Pin-Up Girls
Mar 20 – Apr 25, 2026

The Winter Park Playhouse - Winter Park, FL 32789The Pin-Up Girls - March 20 - April 25, 2026 From The Andrews Sisters to hip-hop and Gershwin to Beyonce,...

NEVER CAN SAY GOODBYE: THE 70s BEEHIVE MUSICAL
Aug 6 – Aug 30, 2026

NEVER CAN SAY GOODBYE: THE 70s BEEHIVE MUSICAL celebrates the unforgettable music of the 1970s, featuring a talented ensemble of six women performing over 30...

THE RAT PACK LOUNGE
Sep 24 – Oct 18, 2026

The Rat Pack Lounge invites audiences to swing back to the golden era of musical entertainment. After Frank Sinatra, Dean Martin, and Sammy Davis Jr....

A CHRISTMAS SURVIVAL GUIDE
Nov 19 – Dec 20, 2026

A Christmas Survival Guide is a light-hearted musical comedy that offers a refreshing take on holiday stress. Created by John Glaudini, James Hindman, and Ray...

NOW COMES THE FUN PART: THE “HOW THE #@&! DID I GET THIS OLD?” MUSICAL
Jan 21 – Feb 14, 2027

NOW COMES THE FUN PART: THE “HOW THE #@&! DID I GET THIS OLD?” MUSICAL is a comedic exploration of the challenges and surprises that...

ALL HANDS ON DECK
Mar 11 – Apr 11, 2027

ALL HANDS ON DECK is an award-winning musical that celebrates the swing era, big bands, and the music of the 1940s. Inspired by Bob Hope's...

SISTER AMNESIA’S COUNTRY WESTERN NUNSENSE JAMBOREE
May 6 – May 30, 2027

Sister Amnesia's Country Western Nunsense Jamboree brings the beloved Nunsense characters back for a lively musical adventure. After Sister Mary Amnesia regains her memory and...



Review: THE PIN-UP GIRLS at Winter Park Playhouse


by Julie Gardieff - April 04, 2026

What did our critic think of THE PIN-UP GIRLS at Winter Park Playhouse?...

Review: COMPANY: A MUSICAL COMEDY at Theater West End


by Albert Gutierrez - March 30, 2026

Theater West End has once again delivered a hit with this production of COMPANY. Opening night was practically sold out, and the energy in the room reflected it – an audience eager to see how this beloved musical would unfold on the intimate Sanford stage....

Review: THE LIGHTNING THIEF at Bay Street Players


by Julie Gardieff - March 22, 2026

What did our critic think of THE LIGHTNING THIEF at Bay Street Players?...

Review: FAT HAM at Orlando Shakes


by Benoit Teves - March 10, 2026

Orlando Shakes’ production of FAT HAM is a sensory-rich, unapologetically Black, and proudly queer reimagining of Hamlet that trades Shakespearean tragedy for hard-won joy. Set against a stunningly detailed backyard cookout, Je’Shaun Jackson’s stylized performance as Juicy anchors a vivid ense...

Review: LILLY AND THE PIRATES THE MUSICAL at Orlando Family Stage


by Julie Gardieff - February 25, 2026

Yo ho ho! Ahoy mateys!  X marks the spot on this musical based on the 2013 novel by Phyllis Root. Lilly and the Pirates is about a 10 year old girl (Lilly) who has a lot of worries.  When her eccentric scientist parents send her to live with a relative while they are in search of an exotic form of...

Review: TIARA'S HAT PARADE at Orlando Family Stage


by Julie Gardieff - February 25, 2026

Tiara’s Hat Parade is based on the 2021 book written by Kelly Starling Lyons and was adapted for the stage by Paige Hernandez. It tells the story of a girl named Tiara Rose who helps her mother in her hat shop, Tracy Rose Millinery....

Review: ANGELS IN AMERICA, PART TWO: PERESTROIKA at Theater West End


by Albert Gutierrez - February 21, 2026

Theater West End was wise to split Angels in America in the season as two separate performances, each with their own block in the schedule. Originally, I was concerned that the Part Two of it all might turn away prospective theatergoers. But upon watching both parts now, and bearing in mind my own f...

Review: MY DEAR DEBBIE at New Generation Theatrical


by Julie Gardieff - February 18, 2026

When it comes to theater, seeing an original work is always a gamble.  Yes, I know that many popular pieces of theater started as original works, but this does not mean I personally want to invest my time in it.  ...

Review: THE 25TH ANNUAL PUTNAM COUNTY SPELLING BEE at Theatre South


by Julie Gardieff - February 15, 2026

What did our critic think of THE 25TH ANNUAL PUTNAM COUNTY SPELLING BEE at Theatre South?...

Review: ROMEO & JULIET at Orlando Shakes


by Benoit Teves - February 01, 2026

In a production that marries 16th-century gravitas with 21st-century urgency, Director Monica Long Tamborello finds a delicate balance between Act I’s playful hope and Act II’s harrowing descent, reminding us that while the feud is ancient, the loss of innocence remains a devastatingly contempor...

Past Shows

From My Hometown
From My Hometown
Jan 23 – Feb 21, 2026

Southeastern Regional Premiere!This critically acclaimed Off-Broadway musical is a "rags to riches" tale of three young men just off the bus from their hit-record producing hometowns -...

Finding Our Way Back
Jun 19 – Jun 22, 2025

Finding Our Way Back is a new musical that explores the lives of sisters Zoey and Paige as they escape their stifling small-town environment for...

Ink & Paint
Jun 19 – Jun 22, 2025

Ink & Paint is a musical that tells the story of the first all-women animation unit at Disney, focused on their work on the film...

Place To Stay
Jun 19 – Jun 22, 2025

Place To Stay is a fast-paced musical comedy about a couple in search of a home in the suburbs. As their quest intertwines with another...

Speakerheart
Jun 19 – Jun 22, 2025

Speakerheart is a new musical featured in the 8th Annual Florida Festival of New Musicals at The Winter Park Playhouse. With music and lyrics by...

Spirit of the Game: The Ultimate Musical
Jun 19 – Jun 22, 2025

Spirit of the Game: The Ultimate Musical follows the journey of Johnny Diskasis, a disgraced former football star, as he returns to his roots on...

Taking Off!
Jun 19 – Jun 22, 2025

Taking Off! is a rollicking musical comedy set in 1967, capturing the glamorous world of air travel. Follow Amelia Dareheart as she dreams of becoming...

Sounds of Desiree: Reprisin' and Manifestin'
May 28 – May 29, 2025

Desiree Montes takes the stage for her solo cabaret at The Winter Park Playhouse, showcasing her talents through a mix of cherished and memorable roles....

An Ode To The Classics
Feb 26 – Feb 27, 2025

Rachel Hope Ihasz brings her solo cabaret debut to The Winter Park Playhouse with An Ode To The Classics, part of the Spotlight Cabaret Series...

Desperate Measures
Desperate Measures
May 12 – Jun 11, 2023

Desperate Measures at The Winter Park Playhouse May 12- June 11, 2023!This witty and wild musical comedy takes the Bard's Measure for Measure and shakes things up! With a toe-tappin'...

Nunsense A-Men!
Nunsense A-Men!
Jan 20 – Feb 18, 2023

Nunsense A-Men! at Winter Park Playhouse (Winter Park, FL) Jan 20 - Feb 18, 2023Hallelujah! This side-splitting musical comedy is the original Off-Broadway musical Nunsense...

Trav'lin - A 1930s Harlem Musical Romance
Trav'lin - A 1930s Harlem Musical Romance
Jan 27 – Feb 19, 2022

Three couples at different stages of life wrestle with the joys and pangs of love in 1930s Harlem, based on the music of Harlem Renaissance...

Book of Merman
Book of Merman
Sep 24 – Oct 17, 2021

Book of MermanBook by Leo Schwartz and DC Cathro / Music and Lyrics by Leo SchwartzOctober 2 - 25, 2020Previews: Oct. 1 at 7:30pm &...

Crazy for Gershwin
Crazy for Gershwin
Jul 29 – Aug 22, 2021

Crazy For GershwinMusic by George Gershwin / Lyrics by Ira Gershwin / Additional Music by Jerome Kern & Harold ArlenConceived by Roy Alan, Todd Allen...

Five Course Love
Five Course Love
May 13 – Jun 13, 2021

Five Course LoveBook, music and lyrics by Greg CoffinMay 14 - 23 & June 3 - 13, 2021Previews: May 13 at 7:30pm & May 14...

Respect: A Musical Journey of Women
Respect: A Musical Journey of Women
Mar 18 – Apr 24, 2021

Respect: A Musical Journey of WomenWritten by Dorothy MarcicMarch 19 - 28 & April 8 - 24, 2021Previews: Mar 12 at 7:30pm & Mar 13...

A Grand Night for Signing
A Grand Night for Signing
Jan 21 – Feb 20, 2021

A Grand Night For SingingMusic by Richard Rodgers / Lyrics by Oscar Hammerstein IIMusical Arrangements by Michael Gibson & John Tunick / Conceived by Walter...

Virtual Cabaret:
Virtual Cabaret:
Dec 18 – Dec 21, 2020

Celebrate the holiday season with this special new one-hour cabaret featuring the fabulous Natalie Cordone! Performing favorite seasonal hits from radio, TV, film and stage,...

Virtual Cabaret: Back Home to Broadway featuring Laura Hodos
Virtual Cabaret: "Back Home to Broadway" featuring Laura Hodos
Oct 23 – Oct 26, 2020

Dont miss this new one-hour cabaret featuring vocal powerhouse Laura Hodos belting out popular songs from a variety of hit Broadway musicals! Laura will have...

Virtual Cabaret: Impossible Dream featuring Shawn Kilgore
Virtual Cabaret: Impossible Dream featuring Shawn Kilgore
Sep 25 – Sep 28, 2020

This new one-hour cabaret will feature professional baritone Shawn Kilgore performing an assortment of well-known songs sung by leading men in popular Broadway musicals including...

Virtual Cabaret: That's Life featuring Kevin Kelly
Virtual Cabaret: "That's Life" featuring Kevin Kelly
Aug 27 – Aug 29, 2020

The incomparable Mr. Kevin Kelly will croon his way into your heart as he performs an assortment of Frank Sinatra favorites with Christopher Leavy on...

The Andrews Brothers
The Andrews Brothers
Mar 13 – Apr 11, 2020

The Andrews BrothersCreated by Roger BeanMarch 13 - April 11, 2020Previews: Mar 12 at 7:30pm & Mar 13 at 2:00pmWhen an Andrews Sisters USO performance...

Beehive: The 60's Musical
Beehive: The 60's Musical
Jan 24 – Feb 22, 2020

Beehive: The 60's MusicalCreated by Larry GallagherJanuary 24 - February 22, 2020Previews: Jan 23 at 7:30pm & Jan 24 at 2:00pmTold from the perspective of...

You're A Good Man, Charlie Brown
You're A Good Man, Charlie Brown
Nov 15 – Dec 15, 2019

You're a Good Man, Charlie BrownBook, Music & Lyrics by Clark GesnerNovember 15 - 24 & December 5 - 15, 2019Previews: Nov 14 at 7:30pm...

Desperate Measures
Desperate Measures
Sep 20 – Oct 13, 2019

Desperate MeasuresBook & Lyrics by Peter Kellogg / Music by David FriedmanSeptember 20 - October 13, 2019Previews: Sep 19 at 7:30pm & Sep 20 at...

How To Marry A Divorced Man
How To Marry A Divorced Man
Aug 2 – Aug 25, 2019

How To Marry A Divorced ManBooks and Lyrics by Brian D. Leys / Music and Lyrics by Clare CooperAugust 2 - August 25, 2019Previews: Aug...

Nunsense A-Men!
Nunsense A-Men!
Mar 16 – Apr 21, 2018

This hysterical musical comedy is the original Off-Broadway musical Nunsense with all of the characters portrayed by men! Think of it as “Mrs. Doubtfire enters...

I Love You, You're Perfect, Now Change
I Love You, You're Perfect, Now Change
Sep 13 – Oct 5, 2013

Back by popular demand!! Dubbed “Seinfeld set to music!” this musical comedy exposes everything you have ever secretly thought about dating, romance, marriage, lovers, husbands,...

8-Track: Sounds of the Seventies
8-Track: Sounds of the Seventies
Jun 21 – Jul 20, 2013

Boogie down through 10 years of ground-breaking music! This Baby Boomers’ dream come true is a fast-paced musical romp through one of the most impassioned...

All Night Strut
All Night Strut
Apr 19 – May 11, 2013

Conceived and originally directed & choreographed by Fran Charnas. Musical arrangements by Tom Fitt, Gil Lieb & Dick Schermesser. Additional orchestrations by Corey Allen. Swing's...

My Way: A Tribute To Frank Sinatra
My Way: A Tribute To Frank Sinatra
Jan 25 – Feb 16, 2013

Created by David Grapes & Todd Olson. Book by Todd Olson. Take a stroll down memory lane with this loving tribute to "Ol' Blue Eyes,"...

Videos