‘Twas the Night gala promises an entertaining evening in support of Theatre Orangeville

October 23, 2025 · 0 Comments

Written By Joshua Drakes

LOCAL JOURNALISM INITIATIVE REPORTER

In less than a month, Theatre Orangeville will host its single most important yearly fundraiser, which acts as the primary source of funding for its productions throughout the season.

The annual ‘Twas the Night fundraising gala will return on Nov. 15, starting at 5:30 p.m., at Hockley Valley Resort in Mono.

Sharyn Ayliffe, executive director of Theatre Orangeville, said the event is their most anticipated night of the year, and that everyone in attendance can expect a beautiful venue and an unforgettable night.

“It’s our longest-running fundraiser, and we’ve never stopped it,” she said. “It is a very exceptional and enjoyable night. Whether you are coming for the amazing entertainment, the great food, or you’re looking to buy auction items, once you get here, you’re going to have a fabulous time.”

Guests will be greeted immediately with appetizers and cocktails as soon as they arrive, and will be able to mingle and socialize for an hour before the entertainment begins at 6:30 p.m. Attendees will then be seated for dinner at 6:50 p.m., and a cash bar will open at that time.

To accompany dinner, Theatre Orangeville has lined up a talented group of performers coming from the Mirvish Theatre production of “Come From Away.” These performers are Broadway veterans, and Ayliffe said that they perfectly capture what Theatre Orangeville wants to show people – that this is who they are, and what they represent. The stage is their home.

“We always like to mix it up with our entertainment, so it keeps things exciting,” she said. “These are big folks that are coming out to our night, they’ve been on Broadway, and it’s fantastic that we are able to wow our audiences with them. We really wanted to tie the entertainment into who we are.”

Alongside the Broadway heavy hitters, another performance will come from Theatre Orangeville’s production of “Rapunzel,” meaning there will be teasers of what’s to come at the theatre at a later performance, and more.

“There’ll also be a handful of performers from our summer Young Company production of ‘Hades Town,’” Ayliffe said. “So the night is also an opportunity to sample the talent and some numbers from our shows. Folks will be able to engage with our programming and see what that looks like on a very personal level.”

Along with the performances and food, a silent auction will also be running for the duration of the night. Guests will have the ability to place bids on over 100 different items, ranging from small to large prizes. The star items are especially noteworthy. Winners of certain bids will have the prize of attending exclusive theatre performances across the province.

“Our artistic director has always auctioned off Stratford experiences, where the AD [artistic director] actually takes a group of people to see a show, and gets the best seats in the house,” Ayliffe said. “They’ll also get a backstage tour and can get an exclusive meeting with the cast of the production.”

The grand prize this year surpasses even that. For a very lucky winner, they’ll get exclusive tickets to the opening of the hit musical, “& Juliet,” at Mirvish Theatre.

“That deal actually includes opening night party invitations to the Mervish Party, and those tickets are completely exclusive; you cannot purchase them – invite only,” Ayliffe said.

Of course, the auction will include numerous other deals coming from local companies and groups around Dufferin-Caledon. These include theatre tickets, sports tickets, and vouchers for restaurants. Local artisans will also auction off crafted items like jewellery.

All of this will be hosted at the Hockley Valley Resort. Previously, the event was hosted at Best Western, but Ayliffe said that the gala had grown beyond that venue.

“We tried to keep the gala in town for as long as we could, and the Best Western was a great partner, but it just became too small for the event – we just outgrew it,” she said. “Last year was actually our first time at our new venue. Everything happens in the ballroom, which is beautifully decorated, so it’s all contained into one room. This means we can keep the auction at the back and the bar can stay open all night, meaning everyone is together.”

Theatre Orangeville is looking forward to raising as much as it can to fund a plethora of new projects next year. With a goal of $80,000 this year, fundraising has proven difficult since the COVID-19 pandemic, but each year the amount of money raised has been growing.

Theatre Orangeville remains optimistic.

“We’ve definitely had a tough few years, financially,” Ayliffe said. “We’ve worked really hard to attract new audiences while nurturing our existing patrons. We wouldn’t be here without the support of the town, and I truly believe that Orangeville is part of the arts, and Theatre Orangeville is the heart of this town.”

With a new ballroom to work with and plenty of entertainment and good food to last the night, ‘Twas the Night is shaping up to be a night to remember.

For more information about the gala, including pricing for tickets and tables, contact Aisling Smith at asmith@theatreorangeville.ca.