The first thing to note about the picture above is that it’s wrong. The tall building on the left is the Hotel McAlpin, at the southeast corner of 34th Street and South Avenue and the cute palazzo is the New York Herald Building between 35th and 36th Streets, Broadway and Sixth Avenue. Herald Square is the messy bow-tie-shaped intersection where Broadway crosses Sixth on a diagonal. Since the Herald Building is north of the McAlpin, we have to be looking north, but the McAlpin is east of Herald Square so it should be on the right. There’s a simple answer: the photo is flipped right to left. This may have been done intentionally so that the big Macy’s sign wasn’t backwards. In any case, here’s the proper orientation and I can now relax:
If you look closely, you’ll see that the Camel billboard, up Broadway (just south of the New York Times Building) is now readable.
But that’s not the point. This photo is labelled at the Library of Congress as 1910 to 1930 and the cars and cloths suggest the 1920s. The most noticeable non-building part of the photo is the Sixth Avenue elevated, which was demolished in 1939 in favor of the new Sixth Avenue subway. The BMT Broadway subway (now the N, Q, R, and W trains) was extended through Herald Square between 1917 and 1920. You can see the streetcars on Broadway; the streetcars on Sixth are hidden under the el. Both sets of streetcars were replaced by busses in 1936. The Sixth Avenue subway was built in this area between 1937 and 1939. (It’s not a coincidence that the streetcar service was converted to busses just before the subway construction: it was far easier to build subways if it was not necessary to keep streetcar tracks intact.) The Hudson & Manhattan subway (now the PATH train) is under Sixth Avenue from 33rd Street (the near foreground), heading south. And the four tunnels carry traffic from the east to Penn Station were already built under 32nd and 33rd Street.
So we’ve got, in addition to the pedestrian and street traffic, three subways, heavy rail, an elevated, and two streetcar Iines. (To be scrupulously fair, one subway did not overlap in time with the streetcars and el.) One might get the idea that this was some kind of transportation hub.