WINTER PARK — It may not be a Phoenix rising from the ashes — there are no ashes to speak of — but there’s enormous excitement brewing about the reopening of the Winter Park Playhouse, the musical theater company returning this summer to its longtime home at 711 N. Orange Ave. in Winter Park, only in a newly renovated theater expected to take the Playhouse experience to a much higher level.

As part of that celebration, the Playhouse is hosting a Grand Opening Gala on July 17 “to christen the new theatre space,” the musical theater company notes.

Where Did The Playhouse Perform This Season?

On Saturday, the Playhouse hosted its final performance inside the Mandell Theatre at Orlando Shakes, which had been its temporary home this past season. For the first time in its 24-year history, the Playhouse team temporarily left its traditional theater so the building could undergoes significant renovations. While that extensive work was being done, the Playhouse’s 2025-2026 Mainstage Series shifted successfully to the Orlando Shakespeare Theater in Loch Haven Park. Saturday night’s final performance of the musical The Pin-Up Girls marked their last show there.

The renovations were made possible after the City of Winter Park received an $8 million grant from Orange County to purchase the Playhouse’s property after the owner put it up for sale. The theater will be leased exclusively to Winter Park Playhouse, and the Orange County grant also provided funds for renovations and improvements to the property, which will include:

• Increased theater seating capacity (from 123 to 172 seats)
• A larger stage
• Dedicated space for the Playhouse’s regular cabaret shows
• Expanded restroom facilities
• and a renewed lobby. 

“We are deeply grateful to Orange County and the City of Winter Park for believing in and supporting The Winter Park Playhouse,” notes Heather Alexander, the Playhouse’s executive director. “After 24 years of service to the Central Florida community, we will now have a long-term home and be able to uplift, inspire and entertain thousands more Orange County residents and visitors each year.”

What’s Coming Up Next For The Playhouse?

Tickets for the Playhouse’s Gala event went on sale on April 11, and quickly sold out at $150 per person. A waiting list is available for those still interested in attending. Call the theatre’s Box Office at 407-645-0145 to learn more.

The Gala begins at 7:30 p.m., and the evening includes:

• A dessert and cocktail reception
• Live music
• A champagne toast
• A ribbon cutting ceremony
• and a special one-hour show celebrating the renovated theater.  

The new theater will open to the public in August with the launch of the 2026-2027 Series featuring 6 new musicals, including:

• Fred Stuart’s Never Can Say Goodbye: The 70s Beehive Musical (Aug. 7-30).

“Put on your platforms, shades and bell bottoms and get ready to party!!  This new musical celebrates the iconic sounds of the 70s that defined a generation!!! Featuring a cast of 6 incredible women singing more than 30 well-loved songs by Heart, Fleetwood Mac, The Jackson Five, Diana Ross, Linda Ronstadt, Gloria Gaynor and many more!!”

• The Rat Pack Lounge by James Hindman and Ray Roderick, with musical arrangements by John Glaudini (Sept. 25-Oct. 18)

“Come swing, sing and savor the days of highballs and high rollers!  After Frank, Dean and Sammy leave some unfinished business on earth, God sends them back for one night to make things right and fulfill their promise to the owner of the Rat Pack Lounge. This musical comedy features the Rat Pack’s greatest hits.”

• A Christmas Survival Guide by John Glaudini, James Hindman and Ray Roderick (Nov. 20-Dec. 20)
• “Do the holidays stress you out?! This light-hearted musical comedy is designed to de-stress and refresh one and all with holiday cheer!  Armed with a copy of “A Christmas Survival Guide,” the characters charge into the holidays searching for the true meaning of the season. Featuring well-loved songs, mashups of old classics and wonderful comedic originals, you’ll learn how to survive the season in ways that are both hilarious and heartwarming.”

• Now Comes The Fun Part: The “How The #@&! Did I Get This Old?” Musical by Lynne Halliday and James Hindman, with music by Jeffrey Lodin and lyrics by Mark Waldrop (Jan. 22-Feb. 14 2027)

“This laugh-out-loud musical dives into the appalling indignities and rude awakenings awaiting anyone lucky enough to make it past that dreaded AARP birthday. From early retirement to the first colonoscopy, from empty nesting to dating again, this new musical is a hilarious celebration of life’s third trimester. You’ll laugh… You’ll cry… You’ll throw out your back laughing and crying! And if you can’t relate to any of this now, don’t worry—you will soon.”

• All Hands on Deck by Jody Madaras & Quincy Marr (March 12–April 11, 2027) 

“Join us for this award-winning show celebrating swing, big bands and the music of the 1940s!  Based on Bob Hope’s 1942 USO tour to the troops in the field, this high-energy musical is filled with Broadway-style tap dancing, heart-warming harmonies, rousing on-air fun, classic radio commercials and sing-along excitement for everyone!”

• Sister Amnesia’s Country Western Nunsense Jamboree by Dan Goggins (May 7–30, 2027) 

“Yee-Haw!! The Nuns are at it again in this hilarious musical hoedown!  After Sister Mary Amnesia regains her memory and realizes she is actually Sister Mary Paul, a former country singer, Reverend Mother gets her a recording contract and a national tour for her newly released album, I Could’ve Gone to Nashville.  Featuring hilarious one-liners and infectious comic tunes, this musical comedy is a knee-slapping blast and rousing fun for the whole family!”

How Can I Get Tickets for the New Season?

The Playhouse is offering 6-Show Series subscriptions at a discount off the established single ticket price, with all 6 musicals available for $282 for adults and $258 for senior adults (62 years and older). A “You Pick 3” Series subscription is also available for $153 for adults and $141 for senior adults. Individually tickets range from $20 to $52. Two preview performances will be performed prior to opening night at $25 per ticket.

6-Show Series subscriptions are on sale now, while “You Pick 3” Series subscriptions go on sale Tuesday by calling the Playhouse Box Office at 407-645-0145. 

Michael Freeman is an Orlando journalist, playwright, and author of the book “Bloody Rabbit”. Contact him at Freelineorlando@gmail.com.