Jack Kerouac’s On the Road, published in 1957, is commonly hailed as one of the seminal books of the postwar Beat Generation. The experience is shaped by the spontaneous nature of a cross-country road trip, with characters soaking up the culture and chaotic relationships around them, seizing the moment, yet allowing the road to guide them. With 2010 upon us, we couldn’t help but wonder how the journey of Salvatore “Sal” Paradise, Dean Moriarty, and the crew might have played out in today’s world of social networking technology. Would the spontaneity of their adventures be hindered or enhanced by the ability to connect with millions of other people at any given moment? Would they have gone to the same jazz club in Chicago if they knew, for example, that one of their old buddies just checked in on Foursquare at the Green Mill? While our very own iPhone app comes with all the bells and whistles a modern-day city surfer needs (with Foursquare integration!), we’ve illustrated On the Road with just a hint of the essential social technologies of today.

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