[MonkeyRonin]

The original 1788 city plan for "Torento Harbour", with a common in the centre and a strict geometric grid of blocks radiating outwards:




What was actually built was a little more haphazard:




Going back to mr1138's point though, as in most places there was really a confluence of competing planning typologies going on rather than one unifying vision. Most of the older streets are based on earlier surveys with lots laid out perpendicular to the lake, which eventually met up with areas later surveyed at a different angle. Some of the roads follow ravines, hills, the lake or other geographic features; some were just built by private developers or through subdivided lots as needed; and some of the windier streets were well-worn native trading routes eventually paved and brought into the municipal road system.

In the late 1800s and early 1900s there were some attempt at carving grand, city beautiful-type boulevards and plazas through the built-up grid, but few of them ever ended up materializing