Where Hemingway’s legacy lingers in Toronto: a walking tour – Toronto Star

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July 19, 2026

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Where Hemingway’s legacy lingers in Toronto: a walking tour

The great writer left Toronto more than a century ago, but some places with meaningful ties to him are still around.

Updated 23 mins ago, July 19, 2026, 2 min read

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Morley Callaghan House.JPG — Morley Callaghan House, 80 Dale Ave. Nick Lachance Toronto Star

As part of its conference in Toronto later this month, the International Hemingway Society suggests visits to these spots as part of a walking tour, limited mostly to downtown — with an option of roaming farther afield.

1. Old City Hall, 60 Queen St. W.: The intimidating Romanesque style and detailed stonework set the tone for the reporting Ernest Hemingway did here: courtrooms, official disputes, and the pressure of daily deadlines.

2. Former Toronto Daily Star newsroom, now First Canadian Place, 100 King St. W.: Where Hemingway learned metropolitan journalism. The current building, gleaming and corporate, reminds us that the urgency and unruliness of Hemingway’s newsroom were a century ago.

3. 1 Yonge St.: Sold in 2000 by the Star, which moved out entirely in 2022, the building still has in its lobby a bulky, single-operator Linotype machine of the sort used in Hemingway’s tenure with the paper — reminding the author’s fans of the labour- and capital-intensive business he managed to escape.

https://misc.thestar.com/interactivegraphic/2026/07-July/17-hemingway/index-1.html

4. Massey Hall, 178 Victoria St.: This historic Toronto venue is one of the places where Hemingway covered boxing matches, exploring his lasting love of the sport. After one 1920 card there, he wrote about mayor Tommy Church’s distracting, glad-handing presence throughout: “Scotty Lisner was taking a bad beating … The mayor’s eyes never strayed to the ring, but he applauded vociferously — whenever the crowd did.”

5. Arts and Letters Club, 14 Elm St.: Hemingway was nominated but never joined — he could not afford the fee. Members of the Group of Seven were socializing in its (still-clubby in 2026) interior, but a stop here serves to remind visitors that he never quite gained entry to those literary and artistic circles.

6. Toronto Reference Library, 789 Yonge St.:A showcase displaying an original copy of Hemingway’s last article for the Star can be viewed in the Baillie Special Collections Centre on the fifth floor.

7. Maison Selby, 592 Sherbourne St.: Hemingway and wife Hadley stayed here in 1923 while awaiting the birth of their first child, John Hadley Nicanor (alias “Bumby”). The restored mansion’s restaurant and speakeasy-style bar let visitors savour the lingering vibe where he lived briefly, filed copy and prepared to leave Toronto again.

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8. Connable House, 153 Lyndhurst Ave.: Hemingway lived here in 1920 while tutoring the son of Ralph Connable, a job he got after a chance meeting with Connable’s wife. More significantly, an impressed Connable — a top executive at the Woolworth department store — used his advertising connections to introduce the struggling young writer to editors at the Star. Freelance assignments followed.

9. Morley Callaghan House, 80 Dale Ave.: This is where the esteemed Canadian author moved in 1951. Though the two men were friends for a time, the house shows how the writers’ paths diverged: Callaghan put down roots in Toronto while Hemingway kept moving.

10. The Hemingway Apartments, 1599 Bathurst St.: Hemingway’s final Toronto residence in 1923. A modest mid-rise typical of the period, it was another temporary address, reminding visitors that though he got work and even started his family here, he never fully settled into this city.

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