The Wonder of it All

A Theatre Orangeville Mainstage Production

World Premiere Written  by:Mark Weatherley

Kingsley considered convincing Charmaine to marry him the greatest achievement of his life. That is, until a surprise from their past meddles with the certainty of their future. After 25 years, is it too late for them to rediscover the redemptive power of love?

Full of humour and heart, the world premiere of the two-act version of The Wonder Of It All is a witty and touching comedy—a comic misadventure for modern lovers.

Content Notice: Please be advised, while this is an enchanting comedy, this show features some mature language.

Opera House Rental 

On November 7th, the Orangeville Jazz Society Big Band joins forces with the dynamic vocals of John Amato for a tribute to the classics of the Big Band Era and iconic crooners like Frank Sinatra, Joe Williams, and Nat King Cole. If you caught their show at this year's Blues & Jazz Festival, you're well aware of the electrifying energy this group delivers. In the spirit of the Basie band, this powerhouse ensemble will captivate you with some of the greatest songs ever sung - and the finest arrangements ever swung.

(Don’t tell anyone… until you’ve got your tickets!)

'Twas the Night Gala...

A Theatre Orangeville Fundraiser at Hockley Valley Resort

Theatre Orangeville’s annual ‘Twas the Night... Gala is the premiere fundraising event of the year, and your ticket is more than just an entry—it’s a direct investment in the future of our Mainstage and Youth Academy programming.

Prepare for a night like no other, where magic and generosity come together for a spectacular cause.

The evening begins with a bubbly reception and hot hors d’oeuvres, giving you the perfect opportunity to mingle and discover a vast array of silent auction treasures. With something for everyone, it’s the perfect way to get a head start on your holiday shopping! Plus, kick off the night with unforgettable performances by some of Theatre Orangeville's most beloved artists, including our very own T.O.Y.S. and Young Company.

Indulge your senses with an elegant, gourmet dinner paired with fine wine, all while enjoying the very best entertainment.

The main event is a thrilling live auction, hosted by our very own Artistic Director Jennifer Stewart and Executive Director Sharyn Ayliffe. Bid on lovingly curated items designed to entice every interest, from exclusive theatre packages to the Shaw and Stratford festivals, to luxurious spa getaways, private behind-the-scenes experiences, and many other surprise delights!

The ‘Twas the Night... Gala is an evening—and an event—that truly sparkles. Don't miss your chance to be a part of the magic.

**Ticket Purchase Deadline - Please Purchase Your Ticket(s)by November 5, 2025**

Common Ground

Theatre Orangeville Mainstage Production

Written By: John Sparway

Pam is blindsided when her husband of four years leaves her a note telling her he’s left her for another woman.

She leans on her best friend Lizzy for support as she picks up the pieces of her life. She gets a call from Jake, a potato farmer (and the other woman’s husband). He is equally bewildered by a similar note left for him. Jake is new to the area and has no Lizzy in his life, so Pam reluctantly agrees to meet him.

Over time, they find common ground in their shared experience. Full of wit, warmth and humour, Common Ground is a heartwarming comedy about love - both lost and found.

The Wedding Party

Theatre Orangeville Mainstage Production

Written By: Kristen Thomson

The Wedding Party takes us behind the scenes with two families, mistaken identities, and love - all tied up in a madcap comedy that invites the audience to take a seat ringside on the big day.

Dress up in your ‘wedding best’ and join our cast (who each play a multitude of hilarious family and friends attending the wedding), as they hit the dance floor, indulge perhaps a little too much, and try to get along.