I'm writing an application that lets you view historical data, and the problem is that most/all map services show only current data. It would be nice if the map reflected the year of the data we're layering on top.
So if you want to make some money, there's an option for you!
https://www.openhistoricalmap.org
I don't think you can pay for it, but I'm sure they'd accept donations!
Perhaps there is a different dataset with better historical accuracy than OSM, but I do not know of one. You'd likely have to reduce your scope: trails in a specific park? Roads in a specific city?
As another commenter notes, there is a sister project OpenHistoricalMap that focuses on mapping historical data. It is rather sparse compared to OSM, but super fun to explore around e.g. NYC.
Especially here in Europe / Germany, where entire quarters where bombed to rubbles newer streets do not match neither namely nor spatially.
I loved how you could "move back in time" in street view. I think that has been killed too? There is a lovely Twitter/X account for Detroit tho: https://x.com/DetroitStreetVu
It's just that in Europe the data is much more sparse to begin with. In many places Google didn't go multiple times, so there just can't be older data. On some streets however I see that if the data was really old (before ~2010/2012) Google probably decided that the quality was so bad – well, it really is – that they do not make it available. So even if there were multiple passes it is not a must that this feature comes available.
has a great selection of historical maps.