The eastern portion of this area (with what is now called the Fashion District) was first planned as the New Town Extension when Toronto was incorporated as a city.

[5] Between Victoria Square (including the former Garrison Burial Ground and the garrison chapel) at Bathurst Street and Clarence Square at Brock Street (Spadina Avenue) Wellington Street was planned as a broad 'Wellington Place',[6] likely modelled after similar large boulevards in the planned Capital of the United States, Washington which had been burned during the War of 1812 in return for the American occupation of Toronto.

[7] Toronto now extended horizontally from Niagara Street (with the Garrison Creek and Common beyond) to the Don River in the East, the area north of Queen having been planned as large estates.

[citation needed] Most of Toronto's institutions and businesses preferred to remain closer to the central city in land subdivided from former 'Park Lots' north of Queen Street.

At the end of the 19th century Toronto carried out a large number of annexations and planned new grand institutional building north of Queen Street in St. John's Ward (now the Discovery District), this led to the deterioration and demolition of many of Toronto's old institutional buildings south of Queen Street with many of the large lots being sold to the expanding Railways.

[6] In the first half of the 20th century many working families immigrated, especially from southern Europe (especially Italy and Portugal), to this neighbourhood.