Thanks, Will.

Can I just add -- and most of you will have already figured this out -- you can get a much higher-resolution version by clicking on the picture. Whether it helps you solve or not, you should do it, because the picture is cool.

Got it. But don't want to reveal the answer so soon. Is there a place we can send the answer to, to not destroy the fun for others?

Dag, that's not the Grand Concourse, is it?

Oh, man, you are fast, rbj.
Sure, you can send me answers at riyank@yopmail.com

I think this should work -- never tried this yopmail thing before, but it's worth a shot!

I can't get it. At first I thought that big building on the upper right was St. John the Divine's... nah.

So the main avenue, fifth avenue, riverside, CPW. I guess I'm pretty manhattan centric.

[4] Must be an rb* thing, because I have it figured out too. I suspect I've seen the picture before.

RBJ has indeed nailed it, using a method that would not have occurred to me.

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?

I see cars. I see a carpenter's shop. I'm useless at this. Not sure how to guess the date.

Leaving my guess via email from babyburke@aol.com.

[5] Think of it instead as, what building might this photo have been taken from?

[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.

Some good detective work already!
GreenMan, impressive, but I believe the sign you focused on is just an advertisement.

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

[8] At least you could figure out the where! I am totally lost on this one, and my strategy of constantly guessing the Brooklyn Bridge falls apart when the picture is not a bridge.

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.

@RIYank - advertisements will getcha every time. I emailed another guess based on something rbs wrote. :)

[13] Basically right! The year is a little later than you guessed, but I don't think that can really be determined from the picture.

[7] I am a professional research librarian.

Are those trolleys on the street on the left?

[8] The pic is taken a few years later than I originally thought, so it's possible (but not likely) some of those vehicles are automobiles.

[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.

[15] Geez, that's right, I knew that but I forgot.
Yeah, are they trolleys? I really don't know. Some of them look like trolleys, but they aren't hooked to any electric lines. Didn't early trolleys have overhead hooks on electric lines?

I know nothing but that looks like Riverside. Unfortunately, I rode a trolley on Westchester Ave. in the Bronx late forties early fifties and there was no overhead that I remember. Maybe pre-Great War circa 1913 because I think I see horses?

[18] Interesting.
I'm certain there were some overhead electrical trolleys in the Bronx in the 1940s. Here is conclusive evidence! I don't think there were NYC cable cars a la San Francisco, but maybe there were at some point. Not in the '40s. How were the Westchester Ave trolleys powered?

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

I guess I should have looked up. On second thought there has to an electrical source to send to the tracks on the street. My excuse is that I was only three or so. Oh well time to watch football and root for the Royals.

Left my guess via email, too.

RIYank - Sent you an email with my guess.

[20] I don't think the tracks were electrified. I think the current went from overhead lines to the trolley via the pole.
[21] Very close.
[22] Not very close :-)

Final comment revealing all at 6:00 EDT...

Hm, I wonder if Will's deadline was too long. The post has slid off the back end.

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.

Uh, I forgot to give the answer explicitly. It's a view from the Dakota down Central Park West in 1890.