The tried-and-true adage for theatrical troupers like Roy Allan and Heather Alexander is, of course: “The show must go on!” But in 2023, there was real doubt about where (if, indeed, anywhere) The Winter Park Playhouse—which the husband-and-wife team had opened in 2002—would stage its wildly popular musical comedies and classic cabarets.
When the venue on North Orange Avenue was set to lose its lease, the news sparked a frantic scramble to find a new location. Although at times the situation seemed dire, this roller-coaster story—like most of the shows at the Playhouse—had a happy ending.
The City of Winter Park—citing $1.9 million in economic impact from the operation—applied for and won an $8 million grant via the Orange County Tourism Development Tax to buy and renovate the building specifically for the Playhouse, which was offered a 25-year lease from the city at $1 per year.
While construction was underway, Allan and Alexander moved the venue’s slightly shortened 2025–26 season to the Lowndes Shakespeare Center’s Mandell Theater in Loch Haven Cultural Park. Playhouse fans followed but knew it wouldn’t be for long.
And it wasn’t. In fact, a Grand Opening Gala is slated for Friday, July 17, at 7:30 p.m. Tickets are $150 per person and the evening will include a dessert and cocktail reception, a champagne toast, a ribbon cutting ceremony and a special one-hour show celebrating completion of the project.
Then the first show of the 2026-27 Mainstage Series, Never Can Say Goodbye: The ’70s Musical Beehive (August 7 to 30), will open. The regional premier of this Fred Stuart-written romp will salute the sounds of the ’70s with an all-woman cast of six who’ll sing hits from Fleetwood Mac, Gloria Gaynor, the Jackson Five, Linda Ronstadt and Diana Ross. The remainder of the new season—five more shows—will run through May of 2027.
Prior to the reopening hoopla, the Playhouse plans to whet our appetites with a solo vocal performance dubbed Baritone to Broadway by Gabriel Preisser, general director of Opera Orlando, at the University Club of Winter Park. The show is slated for Thursday, May 14.
Preisser will sing opera favorites along with such musical theater classics as “Bring Him Home” (Les Misérables), “The Impossible Dream” (Man of La Mancha), “Soliloquy” (Carousel) and more. The performance will begin at 7:30 p.m. and tickets are priced at $30.
Up next will be an installment of the ongoing “Sounds of the World Series” at the Winter Park Library’s Edyth Bush Theater (Thursday, June 11). Details of that event, which is held in partnership with Barbara Chandler Productions, had not been finalized at press time.
“This whole thing has been exhausting, stressful and exhilarating,” says Alexander. “And I feel such gratitude. I’m so glad that our baby is going to go on.” Likewise elated are roughly 30,000 ticket buyers—the number of show attendees during a typical year.
Seasons to come, in fact, will almost certainly welcome far more patrons than that. The remodeled theater space will now seat 173 instead of 123. And there’ll be a second stage in a designated room that will seat about 80 for the ever-popular Spotlight Cabaret Series.
All you have to do is drive by and you’ll see that it’s a new era for the Playhouse. The building’s once-bland façade, typical for the state’s abundance of featureless strip centers, has also been torn down and rebuilt in a Spanish Mission style more in keeping with the aesthetic of Winter Park. Other upgrades include renovated restrooms, a larger lobby and improved accessibility.
Whatever its address, the nonprofit Playhouse remains Central Florida’s only professional musical theater. In addition to its Mainstage Series and its monthly Spotlight Cabaret Series, it sponsors the Florida Festival of New Musicals—an annual event that fosters development of original works.
And its community outreach programs include REACH (Relevant Educational Arts for Children), for underserved youth; and SHARE (Senior Health Through Arts Enrichment), for mobility-limited seniors who live in full-service care communities.
The Playhouse’s location, by the time you read this, will again be 711 North Orange Avenue, Winter Park. For more information about the gala, pre-opening musical events or season tickets, visit winterparkplayhouse.org or call 407.645.0145.
