Here is a fantastic photograph of Herald Square looking North from 34th Street and 6th Avenue in Manhattan, circa 1908. You can see the original New York Herald Building (the namesake of the square), the Elevated 6th Avenue IRT line, old horse carts and early automobiles, along with hundreds of classy, well dressed pedestrians. You can even see down Broadway to the original New York Times Building off in the distance. For reference, here is the Google Streetview from this angle today.
Be sure to click through to the full size (6000px by 4046px) on Shorpy to zoom in on the magnificent detail.