All of the season posters have been about general themes and preoccupations by Don- eg. the flooded office; looking in on a window display of domesticity, and he even echoes these concerns in his intimations with the few people he is close with, (his line about looking at his life from the outside, and trying to scratch to get in). To me, this poster echoes his line about how his life only goes in one direction: forward. (Stop is never an option for Don). Like someone above pointed out, the street signs are his internal compass, pointing to his dread of being revealed for his criminal AWOL from the army, (the police /authorities), which intriguingly is on Maddison Ave., and the other One Way, to the promise of an airplane (boundless horizon, escape, vacation, etc). The season is most likely continuing on in 1967, and into 1968, which was a tumultuous time in western political /cultural history, which could be another reading of the presence of the cops. (They don’t necessarily look like they’re there for Don. It would be interesting if anyone can identify that street corner, and the buildings, (if it isn’t just an imaginary composite).