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The Winter Park Playhouse 2026 Schedule
For those who love theater and entertainment, there is no better place to go than the Winter Park Playhouse! This performance venue has been bringing dynamic local musicals and shows to the Orlando area since its founding in 2002. Experience all of its wonders with tickets to one of its shows!
The Winter Park Playhouse Schedule
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The Rat Pack Lounge
Each performance is generally 2 hours in length which includes one 15 minute intermission.
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| Date / Day | Available Times |
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Thu
Sep 24
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Fri
Sep 25
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Sat
Sep 26
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September 2026
October 2026
November 2026
December 2026
January 2027
February 2027
March 2027
April 2027
May 2027
Full Calendar
The Rat Pack Lounge :
The Rat Pack Lounge is an amazing musical written by James Hindman and Ray Roderick featuring musical arrangements by John Glaudini. Hear the best music from the Rat Pack - Frank Sinatra, Sammy Davis Jr, and Dean Martin - including hits like, "My Way", "Come Fly With Me", and "Ain't That a Kick in the Head".
A Christmas Survival Guide:
Celebrate the holiday season with brand new traditions when you book tickets to see A Christmas Survival Guide, a fantastic musical comedy written by John Glaudini, James Hindman, and Ray Roderick. It features hilarious characters, beloved songs, and comedic flair that will have you laughing during the entire show!
Now Comes the Fun Part:
Catch the premiere of the brand-new Now Comes the Fun Part show, a hilarious musical about the woes of getting older. Whether you're navigating your first colonoscopy or getting an AARP card in the mail, this musical helps you relate to the nature of aging with hilarious and heartfelt moments that will keep you laughing. It runs from January 22 until February 14, 2027.
All Hands on Deck :
This iconic show is based on Bob Hope's 1942 USO tour for troops, and features high-energy, Broadway-style swing and big band music that will have you tappin' along. Tap dancing, amazing harmonies, and sing-along fun await! This musical runs from March 12 - April 11, 2027.
Sister Amnesia's Country Western Nunsense Jamboree:
Hilarious western-style fun and nuns come together for an incredibly funny evening of entertainment with tickets to Sister Amnesia's Country Western Nunsense Jamboree. Join Sister Mary Amnesia as she regains her memories of her past life as a celebrity country music star! This show features comedic songs and so much more for a good ole classic hoedown.
Book Now!
