Heather Alexander

The multi-talented Mr. Bert Rodriguez will return to the cabaret stage with his newest solo cabaret - Mi Familia. Learn how to purchase tickets.

Tay Anderson will bring to the stage the hits of the silver screen in - See You At The Movies -  her new solo cabaret in the popular Spotlight Cabaret Series at The Winter Park Playhouse April 24 and 25, 2024. Playhouse Music Director, Christopher Leavy, will accompany on piano. 

The remarkable Mr. Adam T. Biner takes the cabaret stage at The Winter Park Playhouse to debut his latest solo cabaret - Always A Classic- in the theatre's popular Spotlight Cabaret Series - November 15 and 16, 2023. 

Experience the legendary music of Barbra Streisand as Russell Stephens debuts his new solo cabaret, 'A Piece of Sky,' at The Winter Park Playhouse on October 11 and 12, 2023.

Dustin and Courtney Cunningham will return to the Spotlight Cabaret stage at The Winter Park Playhouse, September 13 and 14, 2023 with their latest cabaret entitled - Musical Memories: The Composers that Shaped Us. Playhouse Music Director, Christopher Leavy, will accompany on piano. 

The Winter Park Playhouse, a staple in the Orlando arts community has opened its 21st season of professional musical theatre with HONKY TONK LAUNDRY, a jukebox musical featuring music from some of the most popular women of country music including Carrie Underwood, Dolly Parton, and Tammy Wynette. This handclapping, foot-stomping musical provides a high-energy and fun evening for theatergoers in Winter Park and opens their season with a bang.

The Kensington and Chelsea Festival in partnership with The Chelsea Theatre has announced the theatre’s summer 2023 Festival Season. Running from 11th July – 30th August, 18 individual performances will span physical theatre, comedy, performance art, children’s theatre, and live music.

Pianist, vocalist, composer and all around outstanding entertainer - Ms. Carol Stein - performs her latest solo cabaret Songs of the Seasons! in the theatre's Spotlight Cabaret Series May 17 and 18, 2023.  

The multi-talented Bert Rodriguez will debut a brand-new solo cabaret - The Rhythm Is Gonna Get You - in the theatre's Spotlight Cabaret Series, April 19 and 20, 2023. 

As part of their quarterly “One-Night-Only” Series, The Winter Park Playhouse will present ELVIS: Aloha From Vegas featuring David Jericko and The Crew on Saturday June 15, 2023 at 7:30 pm.  Net proceeds will go to support the Playhouse's professional musical theatre programming in-house and out in the community.

Central Florida favorite Natalie Doliner will grace The Playhouse Spotlight Cabaret stage with her newest solo cabaret - The Money's In the Basement - celebrating some of our best- loved low voices in the performing arts world.  Playhouse Music Director, Christopher Leavy, will accompany on piano.  

Valentine's Day week will be just that much sweeter when the superb voice of Opera Orlando's Gabriel Preisser graces the Spotlight Cabaret stage at The Winter Park Playhouse February 15 and 16, 2023 in a new solo cabaret - Love Languages. Playhouse Music Director, Christopher Leavy, will accompany on piano.  

As part of its popular One-Night-Only Series, The Winter Park Playhouse will present a 90-minute evening of Billy Buchanan as Ray and Stevie! on Thursday, March 2,2023 at 7:30 p.m.

Kick off the new year with a brand new solo cabaret in The Winter Park Playhouse Spotlight Cabaret Series featuring the exceptional vocals of Ms. Tay Anderson in - Tales From A Hopeful Romantic - January 25 and 26, 2023. 

Stepping directly out of his current role on The Winter Park Playhouse mainstage, Broadway veteran Larry Alexander lights up the theatre's Spotlight Cabaret Series with his latest solo cabaret - Broadway Showstoppers - December 14 and 15, 2022. Playhouse Music Director, Mr. Christopher Leavy, will accompany on piano. 

Caila Carter will debut her new solo jazz cabaret - In A Sentimental Mood – as part of The Winter Park Playhouse Spotlight Cabaret Series,  November 16 and 17, 2022. Playhouse Music Director, Christopher Leavy, will accompany on piano. 

Fall into the season with Mahalia Gronigan and her new solo cabaret - Autumn Moondance - in The Winter Park Playhouse Spotlight Cabaret Series October 12 and 13, 2022. Playhouse Music Director, Christopher Leavy, will accompany on piano. 

A Treasured Tribute to Whitney Houston, Diana Ross, Tina Turner, and Natalie Cole on Friday, October 21, 2022 at 7:30 p.m.

Somewhere on Highway 57 between Frog Level and Smyrna sits a little diner across from a service station where the pie is fresh, the beer is cold, and the gas is cheap (if that’s even possible these days). Such is the setting for the Off-Broadway hit musical PUMP BOYS AND DINETTES. And in its latest production of this feel-good musical, The Winter Park Playhouse delivers a toe-tapping, knee slapping good time.

Special Offer - PUMP BOYS AND DINETTES at Winter Park Playhouse May 13 -June 12