The Library of Congress puts this panorama – which does not include the 1903 image above – at 1910 to 1915 and that’s as close as I can get without spending a week poring over every background building. I think that five-year spread is close enough. As described below, there’s a piece of evidence that points towards 1910 or so, but it’s not really enough to be sure.
The most interesting thing about the panorama is that it’s not actually a panorama. That word, as ordinarily used, implies that all of the photos were taken from the same spot and represent what a person would see if they stood there are turned to see the whole view on all sides around them. The vantage point for these photos changes in order to get good angles to shoot the various buildings. It makes each slice of view look better, and without a drone to hover over Madision Square Park, it was probably the only way to do this, but it’s cheating a bit. In any case, there are nine photos making up eight views (again, see below) that cover the full 360 degrees, but not evenly. On to the first view, NORTH:
That’s Fifth Avenue on the right heading north into the regular grid of midtown, and Broadway on the left, angling up towards Herald Square (where we can see the Sixth Avenue elevated crossing it) and on to Times Square (where we can just make out The NY Times Building). The obelisk in the foreground is the General Worth Monument, which is an actual grave marker rather than a cenotaph. The BMT subway had not yet been built under Broadway, so Worth was not yet vibrating in his coffin in time to the trains. The big white building on the left is the Toy Center; the location of that building and the streets puts us at the Flatiron Building, and the fact that we’re not higher than the Toy Center means we’re looking out a window rather than standing on the roof of the Flatiron.
The big building on the right is 225 Fifth Avenue. Keep an eye out for it as we look NORTH-NORTHEAST:
The big story, obviously, is Madison Square Garden on the right, with the big tower and the four turrets facing Madison Avenue. The dark tower off in the distance is the 71st Regiment Armory at 34th Street and Park Avenue. The lack of tall buildings on the east side means we can see pretty much all of the 59th Street Bridge in the distance. The angle seems to be the same as the first picture. Now, NORTHEAST:
Hey, suddenly we’ve moved uptown. Before we were looking more at the south (right) facade of the MSG tower and now we’re looking more at the west (left) facade. We’re probably on the Toy Center roof. The four big chimneys left of the MSG tower are a power plant on the East River, where it could get coal delivered by barge. The small and very ornate white building on the right is the Appellate Division courthouse. EAST:
Our vantage point has jumped north again. We’re now looking almost due east at the courthouse rather than seeing its long southern wall. The big arched roof is the drill shed of the 69th Regiment Armory, famous as the site of the 1913 Armory Show that was the public introduction of modern art into the US. The tall building on the far right is the printing annex of the Metropolitan Life Insurance company, a building that was not and had no reason to be famous but which serves as a good marker when we look EAST-SOUTHEAST:
Probably the same vantage point as the last shot, but now we’ve got the main building of Met Life on the right, and the recently-completed tower – the tallest building in the world at the time – decapitated in the center. The reason I said we had nine pictures for eight views is that the next picture is the giraffe’s head:
It’s a little hard to see, but it appears that the upper floors of the tower are empty, which is the piece of evidence that I mentioned suggesting that this was 1910, shortly after the tower was completed. On to SOUTHEAST:
The empty floors of the Met Life tower are pretty clear from this angle…and we’ve shifted north again. There’s a tangle of small buildings with what looks like a big loft building on Park Avenue South under construction in the center distance. Now SOUTH:
The Flatiron, center, with Broadway on the left and Fifth Avenue on the right. We’re probably on the roof of 210 Fifth Avenue, the building with the “Lincoln Trust Company” billboard in the first photo. And finally, SOUTHWEST:
And we’ve shifted again, probably to 225 Fifth.
These pictures were almost certainly not taken in one day, and the canvas canopies over the windows tell us it was summer. Except for the photographer’s apparent disdain for the west side (eight photos to cover the 180 degrees from north to south on the east side, one photo looking southwest), I think it gives a pretty good feel for the appearance of commercial New York as it was growing into itself at the beginning of the 1900s.
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