Parts of Newburgh proper are indeed super sketchy, but the area around there is really gorgeous riding, even just ten minutes outside the city. I'm right across the river, in a town that is a fraction of the size, and has more police than their entire city does... Shame, too, as there is so much beautiful riverfront, great housing stock, and a fantastic set of parks, but if you don't police a town, and have a series of corrupt mayors come and go, these things do happen. Heck, parts of the City of Newburgh look like scenes from The Wire.
My hat is way, way off to you on this trip, I don't have the mechanical skills or the patience and spirit to make it on an old bike like that, but it's really fantastic to see folks actually RIDING those pieces of history, and I'm gobsmacked that you are doing it unsupported. Hell of a bold thing. This I will follow :) Good luck.
We've heard that a million monkeys at a million keyboards could produce the complete works of Shakespeare; now, thanks to the Internet, we know that is not true. --Robert Wilensky