The Geospatial Centre at the University of Waterloo has been busy digitizing its collection of historical maps. You can view these vintage Canadian maps at Kitchener-Waterloo: 1955 to present.
The maps available include historical maps of Toronto, Ottawa, Galt and Dundass. Also available is a map of the Centre's 1955 air-photo collection. Both the vintage maps and the vintage aerial imagery have been made accessible using Esri's Swipe & Spyglass Story Map formats. Using these formats means that you can compare the vintage maps of Toronto, Ottawa, Galt & Dundass with the modern map of the same areas and compare the historical aerial imagery with Esri's current satellite view.
Chris Olsen has also used Esri to showcase some vintage maps of Toronto. Toronto Historic Maps presents a series of historical maps of the Canadian city. Toronto Historic Maps includes the 1858 Boulton Atlas of the City of Toronto. You can also explore Goad fire insurance maps from 1880, 1889, 1913 & 1924 and maps from 1818, 1842 and aerial photographs from 1947.
You can view more historical vintage maps of Toronto (and anywhere else) in the David Rumsey Map Collection. If you use the site's Maprank Search to zoom in on Toronto you can find all the available vintage maps of the city
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