The Commissioner's plan is the reason Manhattan has a grid system, and the page for it doesn't reference any fires.
https://en.wikipedia.org/wiki/Commissioners%27_Plan_of_1811
Finally, the streets before the Commissioner's plan took effect are still rather small and twisty.
In the majority of cities laid out on a grid, you can give an address and a street number, and that is enough to navigate to your destination. Houses are numbered according to the cross street, so on 6th ave and 12th st, if my house faces out towards 6th ave, my house address would be 12xx.
For whatever reason Manhattan neglected that particular part of the grid system algorithm.
First time I visited Manhattan this threw me off. Navigation should be reasonable, but instead it is almost reasonable.
Boston also more than tripled in size due to land reclamation, which included leveling some hills. The contours that the current roads follow may have made more sense when Boston Common was a muddy beach and everyone walked to where they were going.
https://www.reddit.com/r/boston/comments/1s92xa/cool_map_of_... https://imgur.com/gallery/0C349u9