Lara Ross thought she was just taking a summer job when she came to work for Muskoka Chautauqua. She didn’t realize she was also taking a deep dive into her own family history.
The University of Guelph student grew up cottaging on Tobin Island, but had no idea that her great-great-grandfather, Joseph Vaughan, was a founding director of the original Canadian Chautauqua Institution. It was Gayle Dempsey – who co-founded the modern iteration of the arts festival with her partner, Gary Froude – who made the connection. “I had no idea about that part of our family history,” says Lara. “It’s been amazing to learn these things I never knew about us.”
Those sorts of deep-rooted connections are stock-in-trade for Muskoka Chautauqua, a festival that thrives on bringing people together. At the annual event, which runs August 1-10, the lines are blurry between creators and audience members, painters and performers, modern arts and historical connections.
“It’s fitting that we hold the festival in Windermere,” says Gayle. “The village is very much a world apart, a place that is at the heart of Muskoka in some ways, but isolated in others.”

The original Chautauqua ran for more than a decade, beginning in 1921. It attracted so many renowned writers that it became known as Canada’s Literary Summer Capital, but it was far more than a writing camp. Actors, musicians, painters, lecturers, and more brought their skills to Muskoka, sharing with audiences and learning from each other.
The modern iteration echoes that model. “We have literature, music, visual arts, Indigenous teachings, lectures, participatory workshops – many of the same things that the original Chautauqua had,” says Gayle.

The interdisciplinary approach remains strong, too. Philippa Cranston Baron will be discussing her book about her brother, legendary figure skater Toller Cranston, who was also a prolific painter. “It’s a writer talking about someone who was a painter and a skater,” says Gayle. “It brings together such diverse communities.”
Among the musical highlights will be a performance by The Sultans of String. “Their documentary film about working with Indigenous artists just won Best Musical Film and Best Soundtrack at the Cannes Film Festival,” says Gary Froude. “They’re a really eclectic band, amazing musicians, and we are so fortunate to have them here.”
The festival will also include guided history walks through the village of Windermere, workshops on everything from copper etching to using graphic arts to share information, a Family Fun Day, and so much more. Some events are free, while others are ticketed online.