I know you're asking for a single place to go, which isn't going to happen until "modern" places that were captured by Google and the like turn into the old places. Sometimes you can dig into old archives and find pieces of things that were digitized. Put enough of them together and you might get some answers. It's difficult and very regional dependent on what was done over the decades. Just finding an online copy of old highway maps is a challenge, and I figured that would be easy. But if you can find some sources, it's fascinating to try and overlay old and new and see just how much has (and hasn't) changed. I've found old roads in my area that were cut up by newer and by lots of development, but are still there, just not connected in the same way.