This is hard. The clearly legible signs are not getting me to an definite answer, and the signs I think would be most helpful are not quite legible -- tantalizing!

I'm pretty sure I know the neighborhood. I believe we are east of Union Square.
I'll worry about the date later, or leave it for someone else -- the horses suggest late 19th c., but the rest of the scene looks later. Interesting.

I'm going to hazard 19th Century, at least latter half. There are street cars, but it looks like trucking is still done with horse & buggy. Edward Gross Moulding Frames (note the olde spelling) doesn't come up with anything

I'm thinking it's the first decade of the the Century. Here's why. I was fascinated by the C.A. Frees Artificial Limbs store (!!) behind the second cart. It led me to another picture of that store and I was able to read that the Shoe Store in the same building is the W.L. Douglas Shoe Co. with a sign that states "Stores in all the principal cities of the United States" clearly visible in the pic. A quick jaunt over to Wiki says the first store opened in 1894 and by 1900 there were 55 stores nationwide. So I'll go with 1903 as a guess, but it could be earlier. Or later. Hmmm...

Where? I have no idea. Somewhere in the Garment District by the shops that are visible. All the way to the left, behind the first cart appears to be a subway stop (Entrance, Uptown Downtown), but I can't see any indication of a stop. This is so frustrating...

Hm, I thought it was Edward Gross publishing. They had two offices near Union Square, but now I think I was guessing the wrong one. Now I'm thinking it's 870-877 Broadway, just north of Union Square.

Where in the pic does it say "moulding frames"? I see some letters after 'Edward Gross' that could say 'pictures', but when I look directly at it, it turns into a blur. (The publishers did mainly publish pictures.)
If it is the publishing company, the picture has to be twentieth century.

Oh, right, nice find for the Artificial Limbs picture -- I think I just found that too. Clearly the same building.

Anybody have any clue what the "Wonders" sign is for? Or the "Churchill" (which couldn't possibly be the famous 49th and Broadway Churchill's, right?).

Oh, man, I had neglected to download the full picture. Now I see the 'frames and mouldings'. I'm still pretty sure it's the publishing company. But now I have a lot more resolution to work with! Can't do it right now, back later.

[5] The Wonders sign is "1¢ (Cent) Wonders". It looks to be attached to a Vaudeville theater or something, but I can't read the sign behind the third and fourth carts.

Besides the "moulding and frames", the other Edward Gross sign says "Pictures", so it looks like a framing/artwork store or shop.

I tried researching the Post Building that has the signs for "Skirts and Cloaks", but couldn't come up with anything.

GOT IT!

It's the Automatic Vaudeville and Crystal Hall on East 14th between Broadway and University. It opened as a penny arcade in 1903, so this photo has to be sometime after that. I'll up my year guess to 1905.

Interesting article about that place here: http://cinematreasures.org/theaters/17576

C.a Frees was listed at 853 Broadway. At least for the 1893 Colombian Exposition -- but that was held in Chicago.

Ohhh, you think we're looking W on 14th? I think you're right.

The tall building with four arches near the top, that you can see in the background, is 4 W 14th. Google it and look at the image.

So the point of view of the camera is right across the street from Union Sq. If you could see the right side of the street, there would be no buildings!

[12] Looks like it. Like it was taken from the South East corner of the park looking West down 14th. If my bearings are correct.

If we are looking at expositions in the area in that first decade of the century, then we have 1) Irish Industrial Exposition of 1905 (drinking?), 2) International Mining Exposition of 1908 (capped?) and 3) The Hudson-Fulton Celebration of 1909.

Not sure that any of them fit with the hints that Chyll gave us. So I'm sticking with 1905. Horses, drinking, fun and capped? Hmm...

AHA...there appears to have been a Work Horse Parade in Union Square in 1908 featuring the Anheuser-Busch Brewery Team, among others. That would fit in with Chyll's clues. It didn't happen until June of 1908, so he season is wrong. But that's as much as I can look into this.

So let's go with 1908, January or February.

[15] TheGreenMan for the win!!! Wowzers, this was a tough one for me to trace, but you all found it in the same amount of time as I did.

All of it is true; you are looking west on 14th Street, and from our perspective I believe we are standing in the trolley tracks between 4th Ave and Broadway. The year is indeed 1908, but I don't know which end of winter it is (January/February or December).

I just found a very interesting site that gives a color-zoned block-by-block layout and historic review of 14th Street and other areas. It pretty much confirms what we see in this picture, including what I came to be certain was a hotel in the forefront (The Hotel Churchill).

However they either missed something or they are going by today's layout of the neighborhood; urban planning could explain why the corner where Edward Gross's establishment sits in the picture would no longer exist according to the NY Songline map. I imagine it was redirected when these buildings were torn down/refurbished, which would explain the dog-leg curve of Broadway at that junction.

Perhaps this was also a function of minimizing or eliminating the hazard of Dead Man's Curve as it was known due to the many trolley accidents (i.e. passengers morphing into flying missles as they were flung out of their seats when the trolley whipped around the corner) that occurred there.

Also of interest is the fact this picture would (if taken much earlier) include the home of one Cornelius van Schaanck Roosevelt, whose grandson Teddy watched Lincoln's funeral procession from a second story window in 1865.

So Green Man, enjoy your River City; you earned it. Everyone else can raise their cream sodas and give thanks for The Banter. If I can, I will present another game on Wednesday, but if not then enjoy the holiday!

Just a little extra:

The Churchill Hotel was torn down in 1921 -- or at least the lot was purchased in June of that year, and the buyer pulled it down. It seems to have been done because the 4th Ave Subway and its excavation made it an unattractive location for hotel patrons.

The same purchase included the Union Square Theatre building, next door, which was once the heart of a vibrant, fashionable arts scene in Union Square, but eventually was turned into a vaudeville house.

(This is from a 1921 NY Times article.)

I say nay to the "neigh" and sigh that it should be "nigh" . Perhaps Chyll was influenced by the horses in the picture.

[18] I sigh as well. The horses spooked and I justly reprimanded. I'll have to be careful in the future; particularly if I mention Dave Winfield, lest one thinks I have an obsession with horses >;)