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The key problem here is a lack of accurate data. OSM is amazing, but is constantly getting improved and closer to realtime "ground truth." Historical OSM data is usually worse all-around, rather than "equally good, but as of year XXXX"

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.

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As a hobby historian (not really haha) I'm interested in old streets and names particularly.

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

You can still go back in time on Street View. There's a "See more dates" link next to the address info in the top left (at least on the desktop Maps interface) that when you click it opens a film strip of different dated captures for that location. Here's the 2007 capture of 1 Embarcadero (outside the Ferry Building in San Francisco) for example: https://maps.app.goo.gl/ArrucFgus9uMvdSaA

Oh yeah, true. Thanks for pointing out.

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.