For a quarter of a century, Winnipeg has set aside one week each October for the most concentrated dose of improvised theatre in the country. The 25th edition of the Winnipeg Improv Festival runs October 21 to 24, 2026, with every show under one roof at the Gas Station Arts Centre, 445 River Ave in Osborne Village. The opening night, Wednesday, October 21, begins at 7 p.m. with what the festival is calling the Home Opener Chaos Kick-Off — a deliberately unruly start that mixes local players with visiting guests in brand-new configurations the organizers describe as "Chaos Teams."
The festival's origins go back to the year 2000, and to a performer who went looking for something Winnipeg didn't yet have. Stephen Sim, who had spent the 1990s writing and performing sketch comedy with the group Higher Than The Ground before forming the improv and sketch company CRUMBS in 1997, began touring Canada and the United States in search of improvisation. His travels took him to Edmonton, where he connected with Rapid Fire Theatre; to Vancouver, where he found Instant Theatre and VTSL; to Seattle, where he met the people behind Unexpected Productions; to Toronto and Second City; and to Chicago and the iO. Those contacts and that education became the seed of a festival meant to bring the wider improv world home to Manitoba. The event was long known as the Winnipeg if... Improv Festival, and it has been staged at the Gas Station Arts Centre since its earliest editions — a partnership that has now outlasted several generations of local improvisers.
Sim remains the festival's founder and artistic director, and he leads it alongside Caity Curtis, the other half of its artistic director team. The festival is produced by The Improv Company, which also runs year-round classes in Winnipeg; those classes feed directly into the festival's local ensemble, which is why the lineup each year reads as a conversation between the city's homegrown talent and the headliners flown in from elsewhere.
The guest list over the years is a reminder of how much reach a mid-sized Prairie city can have when it decides to build something. Past editions have brought in Kevin McDonald of The Kids in the Hall, Tim Blair of TallBoyz, Ken Hall of The Umbrella Academy, Rapid Fire Theatre from Edmonton, Dad's Garage from Atlanta, North Coast from New York City, and Unexpected Productions from Seattle. The festival has also hosted guest-taught workshops alongside the performances, and Sim has described the week in characteristically immodest terms: "Every year, Winnipeg gets to host the most intense week of improv in Canada," he said ahead of the 2025 edition. "We are fortunate enough to bring some of our favourite performers from around the world here for our festival, and to create something cool and funny with our local community. It's the best week of improv in Canada, maybe even the world!"
The 2026 program leans into that mix. Thursday, October 22 brings Snapshot, a night that opens with two duo showcases — Katy Schutte, visiting from the UK, paired with Winnipeg's own Caity Curtis, followed by Kristina and Mason from Montreal, carrying the style of Theatre St. Catherine — before the festival ensemble performs a new format called Snapshot under the direction of Chris Mead, also from the UK. Friday, October 23 is Spooky Scary Skeletons, which splits its evening between two kinds of fright: a playful, funny spooky show directed by Jenna Goldade of Red Deer's Bullskit Comedy, and an eerier piece directed by Schutte, timed, as ever, to land just ahead of Halloween. The festival closes Saturday, October 24.
The venue itself carries its own history into the room. The Gas Station Arts Centre occupies the corner of River Avenue and Osborne Street, where Imperial Oil opened a pumping station in the 1910s; within three years a garage had been built alongside it, and through the 1930s the site was upgraded into the largest Imperial Oil service centre in the city. One of its longtime tenants, Allan Armitage, ran it as "Al's Esso Service" from the early 1950s into the 1970s. Imperial Oil vacated the corner by 1979, and in 1982 an agreement was reached for governments to fund the Riverborne Development Association's plan to build a performing arts centre on the site. On May 31, 1983, the Gas Station Theatre hosted its first performance, featuring local children's entertainer Fred Penner. Forty-three years later, the same stage is hosting the 25th edition of a festival that started with one improviser's road trip.
Tickets for the 2026 festival are general admission, and the Gas Station Arts Centre acknowledges that it stands on Treaty 1 Territory, the home and traditional lands of the Anishinaabe (Ojibwe), Ininew (Cree), and Dakota peoples, and in the National Homeland of the Red River Métis. Shows begin at 7 p.m. each night from October 21 through 24. For anyone who has never seen improv — or who has only seen it on television — the festival's premise is simple: nothing is scripted, nothing is repeated, and the only thing the performers know for certain is that the audience will be there.