Excited to share the experience with his friends, he soon convinced other photographers to join him on escapades, not only to the rooftops of skyscrapers, but also the tops of idle cranes.

It’s a trend that’s taken off, not only in Toronto, where he estimates there are now about 20 photographers "rooftopping," but in cities such as Boston and Chicago as well.

So long planking, and horsemaning—those trends are child's play compared to the new craze: rooftopping. Essentially, you get to a roof, go to the edge, look down, and snap a photo.

Comparing notes on rooftopping strategies, I learned that, although they'd never heard of infiltration or urban exploration, these newfound colleagues of mine weren't exactly novices.