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Canadian Urbanism Uncovered

Street Stories: The “What street am I?” contest

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UPDATE: Thanks to everyone who entered this contest, and congratulations to our winner — Jeff Garkowski. The answers to the questions have been added to the bottom of this post.

Think you know Toronto’s streets? Try your hand at our Street Stories “What street am I?” contest — you could win a one-year Spacing subscription (or subscription extension, if you’re already a subscriber).

To enter, email your answers to the five questions below to, and write “Street Stories contest” in the subject line. We’ll randomly select a winner from all correct entries submitted on or before Sunday, July 6. Good luck! We’ll post the answers on Monday morning.

This street was designed as a military road, cut by the Queen’s Rangers, and named by John Graves Simcoe in honour of his friend — who, as British Secretary of War, was responsible for assigning the Queen’s Rangers to protect Canada.

The first parliament buildings in York were built at the intersection of Front Street and this street in 1797. As a result, it was originally titled Parliament Street. Its current moniker derives from the name of a house that belonged to Major John Small, famous for a duel he fought and won in 1800 against Attorney General John White. Small called his house after his hometown in Gloucestershire, England.

Major John Small’s son was a Supreme Court clerk who maintained a tannery, sawmills, and a cattle farm on a piece of land his family owned east of his father’s famous estate (see question 2). This street was named after him.

Colonel Walter O’Hara, one of Parkdale’s first residents, fought against Napoleon during the Peninsular War in northern Spain. O’Hara owned more than 500 acres west of Dufferin and north of Queen, and he named this street after one of the Spanish villages he encountered during the war. The same village is also reputed to be the site where Roland, knight in the court of Charlemagne, was killed in 778.

This street is named after an inn, which was in turn named after the man who bought it in 1856. It was a wise purchase; the hotel was an ideal resting place for people traveling north from York to Richmond Hill, Thornhill, and Newmarket.

Street Stories is a new regular feature on Spacing Toronto. If you have an idea for a street we should feature in an upcoming installment, email


Answers: 1. Yonge Street 2. Berkeley Street 3. Coxwell Avenue 4. Roncesvalles Avenue 5. Steeles Avenue