Right, the Governors reported to the King, if he ordered a road be built, it was. Maintaining the roads usually required more than a Royal fiat, though. They were often maintained by locals who lived near the roads, during that time just as we have (theoretically) the possibility of being drafted into the military men were usually conscripted into maintenance work for community assets for a week or two weeks out of the year. This mostly meant maintaining the roads.
There were also some arterial toll roads in the colonies. I can’t remember them now but I know when I was learning about Virginia history in junior high there were several historically important toll roads connecting parts of the State.
Actually a lot of what I’ve read about the colonial era suggests some surprising things about all of that:
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Aside from the super wealthy, most people didn’t run up debts. The super wealthy usually did as part of their business operations (especially plantation owners but even large merchants needed credit.)
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Because of #1, most people had more “cash on hand” and “cash savings” than people today. Currency would for most colonists (who were still overwhelmingly yeoman farmers) come intermittently but been spent infrequently. There was not a hyper-developed consumer culture like we have now. Consumer goods, yes, but not a consumer culture. Mind today most people have a lot of regular bills they can’t escape, and then most people decide they need to go into debt for things (house, car.) Yeoman farmers in the colonies had basically only one regular bill, which was their tax assessment on their land. Land was usually held in a family for generations so most farmers were not in debt to purchase their land. Plus, it would make less sense to go into debt to purchase land in that era anyway if all you want to do is live on it / work it.
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Because of all of that, the colonies were actually the most egalitarian period on record in the United States. With the big caveat that records back then are not perfect. Much more egalitarian than today or any point in the 20th century, in terms of the distribution of financial resources. The colonies were also vastly wealthier than Europe per person, but the top tier of wealth in Europe was massive compared to colonial fortunes. [So Europe was wealthier, but with most of it concentrated in the hands of a small elite.]
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Farms of the era afforded a lot of free time, actually. Like anything it had its peaks and troughs, but it’s very realistic for a colonial farmer who was doing well to take a few weeks to travel and stay with a cousin a week or more’s ride away. Now, something like taking a packet shit along the coast or going on a trans-Atlantic voyage was mostly only for the colonial elite. It wasn’t until the later 1810s/1820s that lines like the Black Ball Line popped up that allowed for some level of trans-Atlantic travel for the non-wealthy. Even then it would have been expensive and something most people would never do…later in the 19th century steamship lines began operation and they usually had the space to offer affordable third class berths that were more in the realistic price range for non-wealthy travelers.
I can’t say for sure, but the stereotypical depictions of “cross roads signage” dates back to cartoons drawn hundreds of years ago. I suspect because that is the sort of signage that actually existed.