At the Toronto Reference Library there are sets of Fire Insurance Plans know as Goad Maps after their creator Charles Goad. The oldest ones go back to the 1850's These are highly detailed plans of the city that show the outline and configuration of every building. Because they were used to assess insurance risk they also include building materials and things like lumber yards and coal piles. 
It's really interesting to compare old maps to the current environment. Using Google earth, it is possible to import a scan of a map and place it over the satellite imagery. It's a bit tricky to get the scaling and orientation just right, but once you do, you have a nifty little digital archeology tool. You can shift the transparency of the map to vary what you can see through of the satellite imagery.
Here are some examples. I have taken a map from the 1880's and laid it over Toronto in Google Earth.
You can see how landfill has been used to expand the area of the city. The old water front ran through where the CN Tower is today: more than half a kilometer from the present water's edge. The Skydome, the Gardiner and the waterfront condos would are all built where once there was deep water:
Further west you can see the effect of a now vanished ravine. Over a hundred years ago a substantial ravine created by the now vanished Garrison Creek cut through the city fabric. Today the Creek has been filled in, but evidence remains in the odd curve of streets and a long swatch of public property in the form of schools, city owned housing and parks:
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