Photographers reach for the rooftops

New hobby delivers adrenaline rush and a bird's-eye view

A cloud textured sky in downtown Toronto (Photography by Alanna Swan)

A closer view of the CN Tower (Photography by Alanna Swan)

A view of the CN Tower (Photography by Alanna Swan)

The bright lights of downtown Toronto (Photography by Alanna Swan)

Alanna Swan sitting on the edge of a building in downtown Toronto. (Photography by Alanna Swan)


City skylines, bright blurred lights in the night, and hundreds of feet stretched out below you.

Dangling your legs off the edge of a skyscraper to face your fear of heights is not ideal for everyone, but for Alanna Swan it worked.

Swan, a third-year Advertising and Marketing Communications student at Sheridan, has taken up the hobby of rooftopping.


Toronto skyline during a sunset. (Photography by Alanna Swan)

Rooftopping is a mixture of urban exploration and photography in which photographers take pictures of the urban landscape from dozens of storeys up. Some put themselves in dangerous positions to do so.

Swan first got into rooftopping from being inspired by pictures on Instagram. She admits the first time she tried she didn’t feel like she knew what she was doing.

“The first time I went I felt like a complete amateur,” said Swan. “Now I feel very excited entering a building knowing what lies ahead. It isn’t until I get to the roof that the adrenaline rush starts. It feels like a huge accomplishment making it to the top,” said Swan.

Rafael Goldchain, Sheridan’s Bachelor of Photography program coordinator, speculates that it’s unique perspectives that have made rooftopping become a popular trend on social media.

“Taking pictures from a rooftop gives you a very God-like vantage point, from which you can take very spectacular panoramic views of what you’re photographing,” said Goldchain.

“I think it’s also the sublime factor from that height, knowing what falling would be like. It can be a terrifying experience, especially dangling your feet over the edge. For the viewer you feel how dangerous the picture is, but you are only looking at a picture so you are spared the horror.”

Although rooftopping is a thrilling hobby, Swan describes it as a patient process.

“First you have to find a building and figure out how you’re going to get in. Once you’re in and you’ve made it up the stairs and to the roof that’s when the “we made it” feeling kicks in. From there it’s all about enjoying the breathtaking view and snapping your shots quick,” said Swan.


She considers the hardest part of rooftopping getting into the actual building and getting to the top of it.

A cloudy sky from a tall building with her feet dangling over the edge is an ideal shot for Swan. The clouds make a photo more interesting because they add texture. She enjoys dangling her feet over the edge because it has helped her get over her fear of heights.

While the height may seem like an important factor, Swan cautions that in the end it’s all about the shot.

“The view is always important when looking for the ‘perfect’ spot. It isn’t always about the height,” said Swan. “The best advice I would give to anyone who is looking to get into rooftopping would be to be to not ask other roofers for spots. It’s a lot more fun and rewarding to just explore by yourself and discover your own spots.”

Swan considers rooftopping a hobby, but is trying to make her hobby into a small side business by selling her photos as prints.

People looking to purchase them can buy them off her Etsy or by contacting her on her Instagram.