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blogTO's Chris Bateman explains the origins of the names of some of Toronto's more noteworthy streets. For instance:

Spadina

Spad-ee-na, Spad-eye-na, however you want to say it, the broad, majestic avenue is one of Toronto's cultural hot-spots and a vital thoroughfare. Derived from the Ojibwa word "ishpadinaa" meaning "high or sudden hill", Spadina was the name chosen by Dr. William Baldwin (of Baldwin Street) for his property at the top of the escarpment behind today's Davenport Road. Designed by Baldwin, Spadina Avenue was the name of the street between Bloor and Queen. The section below Queen was known as Brock Street until 1884. Pheobe Street is named for Baldwin's wife.
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