I know the following words that all mean a road of some kind:
What's the difference between all these words? I'd assume size would be one of them, but what is the order if this is true?
There are several that really do not belong.
町 refers to an area, not a road. It refers to a unit of government smaller than a city (thus probably close to what you call a town.)
通り道 means "on a route to commute/school/wherever you are going to." So when you use this word, the topic of the conversation is someone and not the road itself.
街道 refers to long inter-region routes that connected different parts of Japan, the equivalent of highway system back then. Because of this origin of the term, it has a scent of history attached to it, so in modern days you can see roads named as 街道 for nobility.
The remaining words have significant overlaps between them, and while some of them have some neuances that others don't have, I'm not confident if I got the distinction right, or if such perceived neuances are mine alone or shared.
To me, it's somewhat analogus to asking the differences between Blvd/Ave/St/Rd distinctions in the U.S. Sure, Blvd sounds wider in general (just like 通り), but you can find a plenty of counter-examples.