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Theatre Orangeville reflects on 2025 and looks ahead to 2026

January 3, 2026   ·   0 Comments

By Joshua Drakes

It may come as no surprise that 2025 has been a busy year for Theatre Orangeville. From mainstage productions to youth programming, the not-for-profit organization has spent the year finding new and innovative ways to bring stories to life, while continuing its steady recovery from the pandemic.

As the year winds down, Theatre Orangeville Artistic Director Jennifer Stewart and Executive Director Sharyn Ayliffe sat down with the Citizen to reflect on the past year and look ahead to what’s coming in 2026.

From the end-of-year pantomime Rapunzel: A Braid New World to earlier productions such as For The Wonder of It All, Theatre Orangeville continued to raise the bar throughout the season. But when asked to choose a standout moment, Stewart pointed to a production that exceeded even her own expectations.

Coming from Theatre Orangeville’s Young Company, Hadestown: Teen Edition emerged as Stewart’s favourite production of the year.

“I think it’s my new favourite musical, actually. The Young Company just jumped on board and exceeded expectations beyond anyone’s belief,” she told the Citizen.

Stewart said she was deeply impressed by the level of commitment the young performers brought to the production, not just during performances, but throughout the rehearsal process.

“They just worked so hard,” Stewart said. “There were some days where their brain was bleeding out of their ears because they were just like, ‘oh my gosh, these harmonies are so difficult.’”

She added, “The growth that they experienced as performers was immense. When it comes to theatre, you only get out of it what you put into it, and they put so much into it.”

The success of Hadestown came during Stewart’s first season as artistic director – a role she stepped into without fully knowing what to expect.

“I had no idea what to expect coming into this, I didn’t know anyone on the team,” she said. “I just sort of came here open and ready for anything and everything. I was just going to ask questions and observe and learn as much as I could, as fast as I could.”

Stewart said becoming an artistic director has long been a goal, even before she had the language to define it. Now, she’s fully aware of how special the opportunity is.

“This is my dream job, I have been working my whole life to become an AD,” Stewart said. “This is something I’ve always wanted to do, and I’ve gotten to put everything I’ve learned in my whole entire life and career into practice.”

She also acknowledged the weight of following in the footsteps of former Artistic Director David Nairn, a legendary figure at Theatre Orangeville. Rather than trying to replicate his approach, Stewart said she’s focused on bringing her own strengths to the role.

“David was his thing, and I just have to be my thing. I try to pick up and use everything that he’s created and just sort of launch us into the next era,” Stewart explained.

For Ayliffe, who has been with Theatre Orangeville for years, the leadership transition brought understandable uncertainty.

“We all collectively in the organization went into this calendar year a little bit unsure of how the transition was going to roll out,” she said. “And as is the Theatre Orangeville way, some greater theatrical power seems to always have our back, because it’s been such a fantastic transition.”

That transition has unfolded alongside the theatre’s ongoing recovery from the COVID-19 pandemic, which devastated live performance organizations across the country. Ayliffe said the challenge forced Theatre Orangeville to reflect deeply on its identity and purpose.

“It really was a time where we came together as a community beyond Theatre Orangeville to collaborate and make sure that everybody got through,” she said. “We fought really hard to remain relevant over those years. And I think we did a really good job of that, of continuing to be there for the community. We supported other not‑for‑profits by helping them have virtual fundraisers and things like that.”

While the recovery has been gradual, signs of progress are clear. Attendance is increasing, and with it, revenue.

“Artistically, the company is thriving,” Ayliffe said. “Last year, we had over 25,000 tickets sold… that was a 25 per cent increase over the year before. So we are seeing that steady return to theatre.”

Although a full recovery will take time, Theatre Orangeville is not slowing down. Stewart and Ayliffe said the upcoming 2026 season is packed with productions designed to entertain, surprise and draw audiences back through the doors.

“Our next show on the main stage is called Common Ground and it’s a romantic comedy,” Stewart said. “I decided that I thought it would be fun to set it in the 1980s… it’s going to be date night, girls’ night out, come in your 80s best. There’s going to be 80s music playing. It’s going to be an experience, a party.”

Following that production, the theatre will present Murder at Ackerton Manor, a murder mystery inspired by the style of Agatha Christie.

The season will wrap up with The Wedding Party, a production that blurs the line between audience and performers.

“We finish the season with The Wedding Party,” Stewart said. “The twist is that the audience is the wedding, and they are wedding guests… it’s like you’re not only coming to a show, but you’re coming to a wedding.”

Stewart added that audiences should not expect a picture‑perfect ceremony, promising plenty of drama, humour and audience interaction.

Looking ahead, Ayliffe said the theatre’s strength lies in the people behind the scenes.

“We are extremely lucky, because we really do have the dream team,” Ayliffe said. “It’s been really, really hard to do what we’ve done, and they’re all at 110 per cent every day, even on the days where it’s really difficult.”

Heading into the next year and season, Theatre Orangeville is building momentum as it continues to deliver innovative performances while climbing out of the pandemic slump.

With a rich list of productions on the horizon, the theatre company is positioning itself to continue being an innovative cornerstone of Orangeville’s culture.

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