pp. Taking photographs from the roof of a building, particularly one accessed illegally.
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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.
—Vidya Kauri, “Tom Ryaboi: fearless artist, rooftop seer — and just plain badass,” The Globe and Mail, November 10, 2012
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.
—Jen Carlson, “Vertigo-Inducing Trend: Rooftopping,” Gothamist, August 12, 2011
2003 (earliest)
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.
—Ninjalicious, “Journal: Blackout Exploration,” Infiltration, August 15, 2003
Many thanks to Karen H for spying this word from upon high.