Meet your guide in late morning at the the Flatiron Building on23rd Street then head up Fifth Avenue to the Empire State Building at 34th Street. Along the way you will learn the history as it is revealed by the street walls; building heights, widths, faade styles, how they were adapted for re-use over time, over, and over (and over) again.
Then, head south, crossing back and forth along Broadway on our way to 23rd Street. Now youll be going from the old seedy red light district of the Tenderloin to the upper class residential precincts. Broadway here was once a cultural, 'other-side-of-the-tracks' kind of divide, and the stark difference between the low brow district of saloons and brothels, and the fine hotels and homes on the other side of Broadway, is very much evident in those Broadway blocks today. Pass through Tin Pan Alley, the sheet music grind house of the time.
Then, cross into an entirely different history on the other of 23rd Street at Sixth Avenue, the Ladies Mile Historic Shopping District. This preserved-in-amber row of the middle class shopping emporia of the Gilded Age is the heart of Chelsea today. The hard divide between the red light district of the Tenderloin, and the respectable shopping district is still very much evident if you know what to look for. A real time capsule block, a middle class church (the old Limelight night club) and three middle class homes of the 1850s, still stand from before the Gilded Age moved in. A preserved historic district with an earlier residential history accidentally preserved within!
Continue south to 19th Street and then turn east, back to Fifth Avenue. Here, again, the more complicated history of the transitions that passed through this stretch of Fifth Avenue are explained by the buildings themselves. From residential, to retail, to industrial, and back again.
On Broadway, between Union Square and Madison Square, the tour will end on a stretch of blocks that have about the most wonky history of any section of street in the city. A wonderful Broadway enclave that holds perhaps one of the greatest secrets in New York City.