We’re always on the look out for fun maps of NYC and we came across this site recently, NYC Roads by Steve Anderson. It looks like it was laid out in the 1990s but it does have a nice archive of road maps, vintage photographs and more. The road map database goes from 1928 to the 1990s. Here are some highlights:
This 1928 road map of NYC and vicinity shows the state of the roads. Paved in black, improved in dash line and graded or dirt roads in white:
These maps show the development of the parkway system thanks to Robert Moses:
The interstsate highway system gets added in:
For existing and proposed expressways:
The arterial system between NY/NJ/Connecticut is roughly complete, but missing I-78, I-287 and I-95 in northern New Jersey.
For decades, officials looked to span Long Island Sound with a bridge. This website documents the history.