With Designit’s new office in New York, we wanted to explore a problem specific to this city of cities, namely, how the future of transportation and technology will impact society. When people intersect with complex infrastructure systems like transit, their behaviors and social practices are changed in unpredictable ways. The greater New York area is incredibly complex, involving the MTA, NJ Transit, LIRR, NYCTA, MetroNorth, CitiBike, Amtrak, Greyhound, and East River Ferry, to name a few. We chose to look at how these systems were developed and evolved in the past, and understand how tomorrow’s transit futures might also change the rules and behaviors of social interaction.