There's a great, illustrated history of America's highway system—from the Colonial period to the 1970s—that can be read for free on OpenLibrary.
I've just thumbed through it a bit so far, but it reminded me of a book I read a couple of years ago, Consuming Nature: Environmentalism in the Fox River Valley, 1850-1950. That book, by Greg Summers, a professor the University of Wisconsin - Steven's Point, is about how electric and highway infrastructures were built up in Wisconsin. It's also about the socio-cultural changes that led first to the construction of infrastructure and then, later, to fear over what infrastructure had done to the environment. Really super fascinating.
One of the things I learned in both of these books is that early road infrastructure was built and maintained by the local people who used it. In Colonial times, you owed the city or county so many hours of labor every year. And, when they called you up, you had to go out and work on a road crew. Sort of like jury duty. Only sweatier. (Of course, if you were wealthy enough -- or, in the case of colonial Virginia, owned enough slaves -- you could have other people do your labor for you.) In 19th-century Wisconsin, you could substitute labor on the roads for cash road taxes.
One of the fun outcomes of this system, at least in Wisconsin: Really craptastic roads. Turns out, a gang of random citizens, led by another random citizen, is not exactly who you want in charge of your infrastructure. Summers writes:
"Given proper direction, they might have been capable of maintaining the roads. Unfortunately, town officials tended to select overseers from the ranks of their own communities, leaving them with individuals who had no more knowledge or training in the principles of highway construction than the neighbors they were intended to supervise. As a result, the annual parties of local residents organized for the spring roadwork often degenerated into social gatherings, and little improvement to the highways was ever accomplished."
Thanks to Philip Bump for the link to the OpenLibrary book!