In one of the earliest bird's eye views of Toronto you can spot:
If you take a close look at this image, you'll see an abundance of ships in the harbour (very important to 19th century Toronto). You'll also see Yonge St. emerge as the longest road extending north.
At this time, the Garrison River is almost entirely buried. The Don River has already been significantly straightened. The city is becoming more and more industrialized.
The Great Fire of 1904 decimated the downtown core. Toronto spent the next decade rebuilding the Financial District.
By 1929, the Royal York took its place as the centrepiece of the Toronto skyline. There's a new Union Station, and the land south of Front St. has expanded through various fill efforts (land reclamation!).
Here we're looking south across the U of T campus in the 1930s. That's Lake Ontario in the background.
The Canadian Bank of Commerce Building (now Commerce Court) has taken the crown as the tallest building in the city.
It's hard to believe that almost the entire waterfront between Front St. and Lake Ontario was filled with what were called the Railway Lands . Basically all of this land was owned by rail companies.
At this time, Toronto is still very much an industrial city, as demonstrated by the busy waterfront area.
It's here that you can begin to see the modernization of Toronto with the black steel construction of the TD Centre, which marked the rise of the Financial District. You can also see the New City Hall (1965) in behind it.
The rest of the city is starting to get visibly more dense as well.
Here's the CN Tower as it's being built.
Commerce Court West has been completed, and First Canadian Place is on the way.
A population boom has lead to the rise of concrete apartment complexes across the city.
This shot looks north toward Toronto across the Islands in the mid 1980s before the birth of the SkyDome.
The skyline has taken its modern shape, but it still looks sparse, especially between the Financial District and the CN Tower.
The SkyDome appears! (Now called the Rogers Centre).
The Railway Lands (outlined in red) have been mostly destroyed in preparation for the massive CityPlace condo development.
Next time you drive into Toronto, notice that this whole area is filled with condos now.
This photo was taken by Derek Flack from an airplane on his way to Pearson International Airport in 2007.
While Toronto might not be as dense as some cities, you can see an obvious area of heavier development through the downtown core.
In this photo by Jimmy Wu from June 2014, we can see the increasingly dense core of Toronto, and the profound condo development along the waterfront.
Finally, here's a photo by Ravi Pardesi taken high above the Toronto we know today, a city filled with skyscrapers and cranes. For all the development, it's still concentrated in the core. The east and west sides of Toronto are still predominantly low-rise, though a wider shot would reveal density in south Etobicoke.