Anyway, RBJ polished it off like an amuse-bouche at Rockwell’s. Everyone else is competing against a pro, just so you know!

I thought Central Park would be the obvious guess for the trees on the left of the picture, but then you’d still have to work out whether you were looking north up Fifth or south down 8th. (I’d intended to call the posting “North or South?”, which is also connected to ‘Dakota’, but that got lost in the shuffle from me to Alex to Chyll Will.) Very few tall buildings in the background sort of suggests Harlem to me, but of course that’s wrong for 1890. Also, Fifth Avenue had mansions, not shacks, even way uptown.

I still can’t tell what the vehicles are. Some look like sleds, but some really look like cars. But there were no cars – or maybe just a few cars, in all of New York, in 1890. They weren’t commercially produced until a few years later. And I don’t think they’re trolleys, because (i) you can’t see tracks (although the snow might cover tracks) and (ii) I think trolleys were powered by electricity they got from overhead lines, connected by poles sticking out of the top of the trolley, and there aren’t any of those polls.

Anyway, when the Dakota was built just a few years earlier, it was a fantastically opulent palace surrounded by poverty. Soon after this photo, the neighborhood was rebuilt with brownstones and fancy apartment buildings. One building of the Natural History Museum was already built, a few blocks uptown. A completely different world, but ours is inside, about to hatch.

Final comment revealing all at 6:00 EDT…

Some of the vehicles on the avenue in the picture look like sleds to me. But others don’t.

[7] Could be. There was a trolley line on this avenue and I’d bet it was in place by the time the photo was taken.

Are those trolleys on the street on the left?

The when I can try to help out on. Those are definitely telephone poles, so we are after 1876. They look like the kind that deliver power and telephone, so we are after 1882. Might even be 1882 or thereabouts, as I don’t see any wires running from the poles to the houses, or down the side streets. I also don’t see any tall street lights – I’m pretty sure in between some telephone/electric poles is a shorter street lamp on a pole.

Hm, yeah, are those cars on the avenue, or what?

[8] If you look at the large version, those “cars” are being pulled by horses.

Nevertheless, I probably wouldn’t have had guessed the date within ten years, but when I was trying to confirm the location, I found a webpage with the date on it.

I would have approached it the way Ben has, and probably been equally unsuccessful. But can anyone find useful clues in the picture about the When?