Spotlight Cabaret Series
featuring Tay Anderson

July 18 & 19, 2018

Tay Anderson debuts in The Winter Park Playhouse Spotlight Cabaret Series with her latest original solo cabaret, I Was Here.  Join Ms. Anderson as she pays tribute to some of Broadway's greatest legends. Playhouse patrons will remember Tay from her performance on the Mainstage as Lois in the 50's jukebox musical, Life Could Be A Dream.  Playhouse 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 up front in the beautiful lobby bar. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for General Seating.

Buy tickets

Gigolo: The New Cole Porter Revue

Music and Lyrics by Cole Porter
Conceived by Paul Gilger

July 27 - August 19, 2018
Previews: Jul 26 at 7:30pm & Jul 27 at 2:00pm

World Premiere! An audience favorite from last year's 1st Annual Florida Festival of New Musicals, Gigolo uses Cole Porter songs to tell the tale of a handsome playboy and his relationships. Inspired by the life of Porfirio Rubirosa, this musical revue features 25 Cole Porter classics including, "It's De-Lovely," "You're The Top," "Let's Do It" and many more!

Buy tickets

Florida Festival of New Musicals

Extended Stay

Book by Jenny Stafford / Lyrics by Jenny Stafford & Scotty Arnold / Music by Scotty Arnold

Thursday, August 23 at 2:00pm

Friday, August 24 at 4:00pm

Saturday, August 25 at 8:00pm

Owen is full of dreams but short on ambition. Years ago he stopped at an Extended Stay hotel in Indiana--and hasn’t left yet. Plagued by both fear and ennui, Owen finds himself stuck in every sense of the word. However, when Emma arrives, she too is desperate to pull herself out of her own “stuckness” and excel at her job at the front desk--where she is instructed to evict Owen. Joined in their shared anxiety, they struggle to help each other crawl up out of their dark pasts. When Owen’s adventurous childhood friend Ethan arrives, though, he offers Emma a new life. Each in the newly-formed triangle struggles to figure out how to move forward from pasts that threaten to swallow them whole.

Buy tickets

Florida Festival of New Musicals

Miss Isabella Rainsong & Her Traveling Companion

Book, Lyrics & Music by Ross D. Martin

Thursday, August 23 at 4:00pm

Friday, August 24 at 8:00pm

Saturday, August 25 at 12:00pm

While waiting out a storm in an Amtrak train station, a disheveled Traveler shares the story of his three-year journey as the traveling companion of Miss Isabella Rainsong – a captivatingly beautiful guitar. Sharing songs and stories from their journey, Traveler tells how he discovers Miss Rainsong and an Amtrak ticket while contemplating suicide. As they ride the rails, the Amtrak conductors keep Traveler clean and fed while he takes care of Miss Rainsong, learning to play and channeling songs about the journey. Rehabilitated and restored through music, Traveler tearfully leaves Miss Rainsong behind for another lost soul to find her…

Buy tickets

Florida Festival of New Musicals

The Stranger From Seville

Book & Lyrics by Victor Kazan / Music by Kevin Purcell

Thrusday, August 23 at 6:00pm

Saturday, August 25 at 10:00am

Sunday, August 26 at 2:00pm

Set in the Yucatán on the eve of the Mexican Revolution, in a world of both unimaginable wealth and abject slavery, The Stranger from Seville tells the poignant story of star-crossed lovers - a free-spirited young Mexican woman and a gifted young artist newly arrived from Spain - whose blossoming romance is thwarted at every turn by the self-seeking actions of those around them. Inspired by the setting, elements of gypsy rumba, flamenco and regional ‘trova yucateca’ music styles contribute to the fabric of the show’s classic Broadway score.

Buy tickets

Florida Festival of New Musicals

Diamond & The North Wind

Book by Jeffrey Haddow / Lyrics by Jeffrey Haddow & Thomas Tierney / Music by Thomas Tierney

Thursday, August 23 at 8:00pm

Saturday, August 25 at 6:00pm

Sunday, August 26 at 4:00pm

In Diamond and the North Wind, the beautiful and mysterious North Wind befriends a poor stable boy and takes him on flying adventures, teaching Diamond valuable life lessons that help him prevent the greedy real estate tycoon, Tobias Blunt, from destroying the last livery stables in New York City and turning its horses into glue.

Buy tickets

Florida Festival of New Musicals

Somewhere Between

Book, Lyrics & Music by Alan Becker

Friday, August 24 at 2:00pm

Saturday, August 25 at 4:00pm

Sunday, August 26 at 6:00pm

Benjamin is coming of age – ten years late. While the handsome dreamer tinkers on a motorbike with a vague plan to see the world beyond his hometown, his long-time sweetheart tries to push him along the path to marriage, and his well-connected father clears the way for him to have a stable career. Torn, Ben struggles to decide which way he wants to go. When a brash and quirky stranger appears poised to steal Ben’s girl, job, and everyone’s affections, pressure mounts on Ben, while his dad’s growing political ambitions expose old resentments and new financial strains. Somewhere In Between is about a small town slacker who seeks his own path in life, while thoroughly messing up everyone else’s.

Buy tickets

Florida Festival of New Musicals

How to Marry a Divorced Man

Book & Lyrics by Bryan D. Leys / Music by Clare Cooper / Based on the book by Leslie Fram

Friday, August 24 at 6:00pm

Saturday, August 25 at 2:00pm

Sunday, August 26 at 12:00pm

Layla Diamond, a rock and roll reporter in her late 30’s, decides it’s time to settle down. Following the advice of her daffy mother, she adopts what she thinks is her best option, a divorced man. She sets her sights on a charming sports agent with a needy ex and two obnoxious children. Frustrated, she tries setting up the needy wife with a new boyfriend, which backfires. While trying to fix her Divorced Man’s problems, Layla makes one miscalculation after another, adopting false identities, causing multiple mix-ups, and turning her marital quest into a hilarious farce.

Buy tickets

I Love A Piano

Music & Lyrics by Irving Berlin
Conceived by Ray Roderick & Michael Berkeley

September 21 - October 14, 2018
Previews: Sep 20 at 7:30pm & Sep 21 at 2:00pm

This glorious musical looks at America through the perceptive and hopeful eyes of the legendary Irving Berlin! It follows the journey of a piano from its first days in Tin Pan Alley to the 1950's. The story comes to life with over 60 of Berlin's most beloved songs including "Blue Skies," "There's No Business Like Show Business," "Cheek To Cheek" and "God Bless America."

Buy tickets

Curtains Up 2018!

A Benefit

Saturday, October 20, 2018

6:00pm - 10:00pm

Join us for a spectacular gala evening of theatrical merriment featuring your favorite performers in an outstanding, one-of-a-kind musical show, delicious food, an open bar and exciting online and live auctions!

$150 per ticket.  All proceeds directly support The Playhouse's year-round programs serving adults and children in our community.

Buy tickets

Winter Wonderettes

Created by Roger Bean

November 16 - 17 & November 29 - December 16, 2018
Previews: Nov 15 at 7:30pm & Nov 16 at 2:00pm

The well-loved Wonderettes are back and better than ever! This whimsical musical comedy finds the four-girl singing group entertaining at the annual Harper's Hardware Holiday Party. When Santa goes missing, they use their charm, talent and creative ingenuity to save the day! Featuring fabulous 60's versions of holiday classics including "Santa Claus is Comin' to Town," "Jingle Bell Rock" and "Winter Wonderland,"

Buy tickets

Ain't Misbehavin'
The Fats Waller Musical Show

Conceived by Richard Maltby Jr. & Murray Horwitz
Created by Richard Maltby Jr.

January 25 - February 23, 2019
Previews: Jan 24 at 7:30pm & Jan 25 at 2:00pm

This high-energy all singing, all dancing revue evokes the delightful humor and infectious spirit of the American original Fats Waller! Featuring 30 songs he made famous in a career that ranged from the Cotton Club to Hollywood and concert stages across the world including "The Joint Is Jumpin'." "I Can't Give You Anything But Love" and "Ain't Misbehavin'!"

Buy tickets

What A Glorius Feeling! The Story Of Singin' In The Rain

Written by Jay Berkow

March 15 - April 13, 2019
Previews: Mar 14 at 7:30pm & Mar 15 at 2:00pm

Southeastern Regional Premiere! This new song-and-dance musical brings to life the little-known story of the love triangle between Hollywood legends Gene Kelly, Stanley Donen and their assistant Jeanne Coyne during the creation of the greatest movie musical of all time, Singin' in the Rain. Featuring a score of well-loved songs and some of Hollywood's most exciting and enduring dance choreography!

Buy tickets


Book, Music & Lyrics by Amanda McBroom
Created by Amanda McBroom & Bill Castellino

May 10 - 19 & May 30 - June 9, 2019
Previews: May 9 at 7:30pm & May 10 at 2:00pm

Central Florida Premiere! A beautiful and comedic musical about a woman's journey as she grows up, grows older and finds new happiness along the way. Filled with tremendous humor and insight, this contemporary musical illuminates the age-old conundrum known as "self-discovery." Featuring 20 songs by Amanda McBroom, including her hit song, "The Rose."

Buy tickets


Ticket Pricing

Mainstage Productions
$15 - $42

Spotlight Cabarets
$20 (plus a one-drink minimum)

Special Events
Prices vary.

Please see individual performances for specific pricing information. 



PLEASE NOTE: There will be a $2 per ticket convenience fee to purchase online.

Have a code?

If you have a coupon, gift certificate, or pass code, please enter it here: