Rooftopping Photography Freaktography

Rooftopping Photography – What’s it Like up There? (a photo essay)

Rooftopping Photography, we have all seen the dozens of media articles and blogs about this – so this surely is not the first, it won’t be the last, and it is not going to be the best.


Recently, my friend Neil Ta wrote about how he is “F***ing Done” with it, then – in response to that, Tom Ryaboi wrote about how he will do it Until the Day he Dies and most recently, Bradley Garrett analyzed the subject in this very detailed article.

What I hope to bring forward in this photo essay about Rooftopping Photography , is a different and simplified perspective.  I have been contemplating this piece for quite some time, but struggled with what the angle would be.  It came to me recently when I was interviewed by CTV News Toronto on my experiences in Rooftopping.  The young journalist asked me such a simple question, he didn’t ask me about trespassing, he didn’t ask me if I was afraid of falling and he didn’t ask me if I’ve ever been caught.  His simple question?

“So, what’s it like up there”

That was my angle!

I don’t care to talk about Daredevils, dangling feet or crazy Russians – not that I have any problems with those who push the boundaries – I applaud these game changers and I look forward to the next crazy batch of shots from Mustang Wanted and the next insane climb by James Kingston, and who can forget when Vitaliy Raskalov (@raskalov) and Vadim Makhorov (@makhorov) almost made the whole world vomit with these amazing shots from China?

What I do want to talk about and share with the few of you who read this, is the experience of being on a roof.

What’s it like up there?

My first time on a rooftop in Toronto came by accident in the summer of 2012, I stopped in to see a local “abandoned” ballroom in a downtown hotel – not really abandoned, just not used since the 50’s.


The roof of this hotel was, at the time, considered the village Bicycle of rooftops and was one of the easiest to access.  I had not yet really shown much interest in “Rooftopping” and at the time my sole focus was abandoned houses and buildings.  However, having seen the rooftopping pics from the guys in Toronto – I knew it was a thing.

It was late August and the weather was perfect, I stopped in on my way to work so I was able to experience the early morning hustle of the city from above for the first time.  Looking down from less than 20 floors up was all I needed, this was a fresh new feeling for me and I knew I would want to try this again.  I felt like I was being watched, surely I was from the people in the buildings across the street, and the fact that a maintenance worker could come out at any minute kept my adrenaline flowing and only added to the excitement.

I would end up returning to this roof again on a cold night in December 2012, the night experience was much different, a certain buzz and humm overtakes the city, and the sound is non-stop.

Directly across the street from the building I was on was a movie set, I could hear the director on his mega-horn directing the crew.

This experience was small potatoes compared to the stuff I had been seeing from guys like Neil Ta, Jonathan Castellino, Ronnie Rip and Tom Ryaboi – they may not have known it at the time, but they were laying the groundwork for what would, in less than 2 years, become a cultural and worldwide sensation.

Rather than take you on a journey from roof to roof in chronological order, I think the angle of this story calls for themes, or experiences.  Sunset, weather, vibes, sights and sounds – again, “What’s it LIKE up there?”  I felt it was important to start off with my first time for some background.


One of the greatest things about standing atop a roof of a skyscraper or the top of a tower under construction is getting there in time to watch the sun set.  The city literally changes by the minute, as the sun drops all of the colours change, the sky, the windows, the reflections.

Blue Hour:

Just after the sun dips below the horizon, the city takes on an entirely different look.  As the sun continues to drop past the horizon and the city starts to become dark, the whole city takes on a blue hue. Here are a few examples of how it looks from above.


Lots of buildings in the surrounding areas of the roofs I’ve been on have terraces or balconies or rooftop access for those who live in the buildings.  I’ve looked down from 56 storeys up and seen a group doing yoga on another roof, I’ve seen people having dinner on a rooftop terrace, I was on a roof one night when a couple who lived in a condo across the street came outside a waved to me, curiously watching me the whole time I was up shooting.

The City:

Quite possibly the main attraction when roofopping is the cityscape, the lights, the buildings, the long and winding streets.  Hearing the ambulances scream through the city, watching the taxi’s zipping in an out and watching as all the condo lights blink on and off all around the core.

City Growth and Construction

Standing atop a 60, 70 or almost 80 storey building in a city like Toronto gives one a front row seat to watching a city grow in real time. When photographing on a rooftop, I think we are capturing the growth of a city and years from now people will look back at the roof topping movement currently happening and they will see how a city like Toronto grew to what it will be in the future.  We will see how a city was forced to grow vertically when there was no more room to grow at the surface level, we will also see the progression of building design and how creativity in architecture can transform a skyline over time.

Straight Down:

Many of the most popular images taken from rooftoppers are the ones where the camera is pointed straight down, the amazing thing about these photos are that they give the viewer the sensation of vertigo, even though they are only looking at a screen or a printed photo.  The feeling/sensation of leaning over the ledge of a roof and looking straight down is one that must be experienced, if you can stomach it – but what I love about these photos is the fact that they can make the viewer actually experience a sensation, just by looking at it.

The City at Night:

I’ve spent most of my time on roofs and construction sites late at night, and that is by far my favourite time to be up.  I’ve spoken of the constant buzz of the city, the honking horns, the sirens, the chatter that, oddly enough you can hear from 50-60 floors up.  But aside from the sounds of the city – being at the top of a major city at night just feels good.  It’s calm and peaceful and more relaxing than you could ever imagine.  And the sights are amazing, the other buildings lit up, the light pollution off in the distance and the constantly changing sky.  It’s like having the entire city all to yourself, with no one to interrupt you.

While I could probably find a dozen other things to mention that will describe what it feels like to be up on a rooftop, this photo essay has gone on long enough and I hope I have done my job at giving you an idea of how it feels to experience this thing called Roof Topping.  If I wanted to keep going, I still have a full list of other things to tell you about, but perhaps you can imagine them on your own…..

  • I could go on and write about what it’s like to be on a roof alone and what it’s like to climb with friends.
  • I could talk about what it’s like on a warm summer night, a cold winter night or even on a quiet foggy night.
  • I could talk about the few things experienced on a rooftop that I never expected, like coming face to face with a Peregrine Falcon at 56 storeys high in the Toronto core, or discovering that there are gargoyles atop a hotel roof in Vancouver.
  • Selfies
  • Another great topic could be the differences between a construction site and a rooftop.
  • I could tell you what it feels like to climb up 65 storeys in the dead of winter wearing full winter gear – boots and all.
  • You could learn how it feels to climb 70 stories in hot and stuffy stairwells of a construction site in the middle of summer
  • And lastly, I could tell you all about climbing 60 storeys only to find the roof access door to be locked and then to find security waiting for me in the stairwell when I go to climb back down!

But those are all stories for another day, or not. I hope you have enjoyed this write up and the accompanying photos. You can follow along with all of my adventures on and off the roofs at any of the following links below.


Ello | Facebook | Twitter | Instagram | 500px | Tumblr | Pinterest |

Also, here is a list of some of my favourite photographers who post shots from their adventures on rooftops, cranes and construction sites.  I can’t possibly list them all, but here goes!







5 thoughts on “Rooftopping Photography – What’s it Like up There? (a photo essay)”

  1. As an amateur photographer, how can I go on the roof to take pictures because most buildings in downtown don’t let me go up

  2. I would love to go rooftopping, seriously, I’ve known about it for maybe eight months now and I’ve become somewhat obsessed. Sadly I live in such a desolate state that there aren’t any buildings here tall enough to get the same affect. I hate it here, nothing ever happens haha.
    But I’m worried that if I ever do get the chance to go rooftopping, that I’d be caught and it’d close off opportunities for me. (I’m a student looking to go into forensic work, not good if I suddenly am caught w/ a criminal offense haha.) One other worry is that now that everybody knows about it and that it’s blown up on the internet, that cities are going to start becoming more strict with their rooftop access regulations.

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