NEVER CAN SAY GOODBYE, THE RAT PACK LOUNGE, A CHRISTMAS SURVIVAL GUIDE & MORE Set For Winter Park Playhouse 2026–2027 Season
The 24th season will launch with the reopening of the renovated Winter Park Playhouse venue.
The Winter Park Playhouse has announced its 2026–2027 Mainstage Series, marking the company’s 24th season of professional musical productions. The season will begin following the reopening of the theatre’s renovated home on North Orange Avenue in Winter Park, scheduled for August 2026.
The six-show lineup will feature a mix of Off-Broadway titles and regional premieres.
NEVER CAN SAY GOODBYE: THE 70s BEEHIVE MUSICAL
August 7–30, 2026 (Previews: August 6 & 7)
The season will open with this Southeastern Regional Premiere celebrating the music of the 1970s, featuring songs by artists including Heart, Fleetwood Mac, The Jackson Five, Diana Ross, Linda Ronstadt, and Gloria Gaynor.
THE RAT PACK LOUNGE
September 25–October 18, 2026 (Previews: September 24 & 25)
This musical comedy imagines Frank Sinatra, Dean Martin, and Sammy Davis Jr. returning for one night to fulfill a promise, featuring songs such as “My Way,” “Come Fly With Me,” and “Everybody Loves Somebody.”
A CHRISTMAS SURVIVAL GUIDE
November 20–December 20, 2026 (Previews: November 19 & 20)
The holiday production follows characters navigating the season with humor and music, combining classic songs, mashups, and original material.
NOW COMES THE FUN PART: THE “HOW THE #@&! DID I GET THIS OLD?” MUSICAL
January 22–February 14, 2027 (Previews: January 21 & 22)
This Southeastern Regional Premiere explores aging through a comedic lens, addressing life milestones and transitions with music and humor.
ALL HANDS ON DECK
March 12–April 11, 2027 (Previews: March 11 & 12)
Inspired by Bob Hope’s USO tours, this musical celebrates 1940s music with tap dancing, radio-style performances, and period songs.
SISTER AMNESIA'S COUNTRY WESTERN NUNSENSE JAMBOREE
May 7–30, 2027 (Previews: May 6 & 7)
The season will conclude with this installment of the Nunsense series, following Sister Mary Amnesia as she pursues a country music career.
Ticketing Information
Six-show subscription packages and “You Pick 3” options will be available, with pricing tiers for adults and seniors. Individual tickets will range from $20 to $52, with preview performances offered at a reduced price. Subscriptions and tickets will go on sale in phases beginning in spring 2026 and can be purchased through the Playhouse box office or at winterparkplayhouse.org.
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