Cal Berkeley graduate student Geoff Boeing conducted a fascinating analysis of the street layout of major cities in the US and Internationally. Meaning, how is a city’s street layout oriented relative to a traditional compass – how true is the layout to a North/South/East/West layout? Across most major US cities, the orientation follows that of a compass. However, to no one’s great surprise, Boston fails spectacularly in this analysis (as does Charlotte, NC for some reason).
Although [Boston] features a grid in some neighborhoods like the Back Bay and South Boston, these grids tend to not be aligned with one another, resulting in a mish-mash of competing orientations. Furthermore, these grids are not ubiquitous and Boston’s other streets wind in many directions. If you’re going north and then take a right turn, you might know that you are immediately heading east, but it’s hard to know where you’re eventually really heading in the long run.
Geoff Boeing
This makes it harder for unfamiliar visitors to navigate Boston than many other US cities. It does not adhere to a straightforward north-south-east-west pattern (or any other consistent, predictable pattern) that our brains adjust to in most places, not because Boston apocryphally paved over its cow paths, but because of its age, terrain, and annexation of various independent towns.

When you look at how the International cities trend from the lens of this analysis – old, European and Asian cities that have been around forever and basically just evolved and expanded with no set ‘urban plan’ from their ancient origins – it makes sense that some of the older US cities follow the same ‘organized chaos’.
So next time you’re driving around Boston, you can take some solace in knowing that driving around there is not for the faint of heart.