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In Ride, the musical that closes the Winnipeg Jewish Theatre season, a Latvian-born American woman with an unmistakably Jewish surname attempts to circumnavigate the globe on two wheels in 15 months or less just before the sharp turn of the 20th century.

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In Ride, the musical that closes the Winnipeg Jewish Theatre season, a Latvian-born American woman with an unmistakably Jewish surname attempts to circumnavigate the globe on two wheels in 15 months or less just before the sharp turn of the 20th century.

But as she speeds toward renown on her Columbia bicycle, pedalling her way toward becoming a proto-feminist model for women’s independence, Annie Cohen Kopchovsky — born in 1870, died in 1947 — faces a fork in the road: to retain her heritage, or to ease her passage across borders through the all-too-common sacrifice of acceptance through anglicization.

For director-choreographer Lisa Stevens, the production is relevant in 2026 for the same reasons that the story of “Annie Londonderry” was captivating in 1894.

Ruth Bonneville / Free Press
                                Berkley Silverman (left) and Colleen Furlan star in the story of Annie Londonderry’s 1894 trip around the world on her bicycle.

Ruth Bonneville / Free Press

Berkley Silverman (left) and Colleen Furlan star in the story of Annie Londonderry’s 1894 trip around the world on her bicycle.

“We’re still asking the same questions: who gets to be seen, who gets to be heard, who gets to be believed and how one needs to reinvent themselves, or hide, to be able to survive,” says Stevens. “Who has to change their persona in order to thrive?” As the rider asks, “How far do I have to go in order to move forward?”

Starring as Londonderry (née Kopchovsky) is Berkley Silverman, a Toronto-raised performer who will star in the titular role later this summer in the Charlottetown Festival’s vaunted staging of Anne of Green Gables.

As a Jewish performer, Silverman could relate to the pressures faced by Annie, who took on her ultra-anglo pseudonym as a condition of sponsorship from a New Hampshire spring-water firm of the same name.

In the intersecting worlds of Judaism and performing arts, Londonderry’s transformation isn’t unique: before winning a Tony as Judy Holliday, the star of Bells Are Ringing was born in Queens as Judith Tuvim; all Judy did was translate the Hebrew to English and singularize the plural of her inherited surname. Lauren Bacall? Don’t you mean Betty Perske?

Raised a century after Londonderry’s legendary trip, Silverman’s taking the role allowed her to further appreciate the emancipatory power offered by the 19th-century proliferation of the bicycle — a means of transportation that suffragist Susan B. Anthony said granted its users access to “free, untrammelled womanhood.”

“I love to do a spin class and I like to ride my bike in the summer a lot. Especially when I was a kid: that was my time to explore. I had that freedom,” says Silverman, who’s voiced the husky pup Everest on Paw Patrol for over a decade. “I have a sister who’s six years older than me, so when I was a kid, she was a teenager, and she’d watch me ride my bike to the nearest convenience store to get a popsicle.”

Starring alongside Silverman is Colleen Furlan, who plays Martha, a secretary at publisher Joseph Pulitzer’s New York World, where Annie would for a time write stories under the pen name Nelly Bly Jr.

“Annie enlists Martha in telling her story,” says Furlan, who will appear as Elle Woods’ trusty salon pal Paulette in this summer’s production of Legally Blonde at Rainbow Stage.

Ruth Bonneville / Free Press
                                Silverman portrays Annie Londonderry, the first woman to cycle around the world.

Ruth Bonneville / Free Press

Silverman portrays Annie Londonderry, the first woman to cycle around the world.

“Martha doesn’t have all the details, so you get to watch Martha on this arc of not really being willing to participate, before tapping into that wonder and imagination.”

“When we see the arc of Martha, it’s kind of the arc of all women who would have been impacted by what Annie accomplished and what she wrote about,” Stevens says.

Making its Canadian debut at the Berney Theatre on Saturday, Ride — written by Freya Catrin Smith and Jack Williams — had its world première at London’s Vault Festival in 2020, where it won the People’s Choice Award.

The production is the final show in Winnipeg Jewish Theatre’s proper 2025-2026 season before the company’s co-production in September of Fiddler on the Roof at Rainbow Stage, the first such collaboration between the two performing arts organizations.

winnipegfreepress.com/benwaldman

Ben Waldman

Ben Waldman
Reporter

Ben Waldman is a National Newspaper Award-nominated reporter on the Arts & Life desk at the Free Press. Born and raised in Winnipeg, Ben completed three internships with the Free Press while earning his degree at Ryerson University’s (now Toronto Metropolitan University’s) School of Journalism before joining the newsroom full-time in 2019. Read more about Ben.

Every piece of reporting Ben produces is reviewed by an editing team before it is posted online or published in print — part of the Free Press‘s tradition, since 1872, of producing reliable independent journalism. Read more about Free Press’s history and mandate, and learn how our newsroom operates.

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Updated on Wednesday, April 15, 2026 6:32 AM CDT: Adds link

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