Tom Ryaboi

“Rooftopping” – (Part 2: An Evolving Subculture)

In a previous article, “Rooftopping – Part1:  The Beginning” I introduced a craze in photography known as rooftooping that many urban photographers are exploring.  I communicated how rooftoppers were not particularly thrilled exposing where they shoot from and exposing their secrets.  Understandably because they often gain access by trespassing onto the properties they are shooting from.  The images often raise curiosity among the viewers leaving them to wonder where exactly they were captured from.  In the instances where the viewer is familiar with the city it is not too difficult to pinpoint the general vicinity where the photo was shot. However, figuring out the exact building tends to be more complicated.

Image courtesy of Vitaliy Raskalov & Vadim Makhorov |

I want to make it clear that I am not revealing any secrets.  Many well-known rooftoppers openly discuss their experiences and post videos of them in the act.  I am friendly with several local rooftoppers therefore, it is not my intention to upset anyone.  I want to be able to share some incredible images by extremely talented young photographers, most who are self-taught.  As well as, acquaint readers with what is typically involved in such extreme photography.

Image courtesy of Vitaliy Raskalov & Vadim Makhorov |

Many rooftoppers have a venue they wish to conquer.  They then investigate what is involved with entering the building and climbing to the top.  The more extreme rooftoppers will desire to climb a building that no one has conquered as of yet to be the first to gain the coveted title.  Some are willing to soar to the very top of a building while the more conservative are happy simply photographing with their feet firmly planted on a flat roof.  It is common for many to ascend hundred foot cranes, dangle their feet over the edge of buildings and walk on thin ledges to name a few.  All in hopes of obtaining an image that elicits a shock factor among viewers.

I have come across certain forums where some readers get agitated by the risk involved in these daredevil attempts.  Not only are they putting themselves in danger but if they were to fall from such great heights they could potentially take an innocent victim’s life.

Image courtesy of Vitaliy Raskalov & Vadim Makhorov |

In some instances, when the coveted buildings are under construction they are commonly fenced off and locked.  In like situations it is not terribly difficult to enter however, one has to be willing to trespass.  Often rooftoppers are eager to risk the consequences involved when entering newly constructed complexes.  They believe that once they have gained access to the building they are scot-free. They conclude there is a lesser chance involved being caught once inside.

Image taken by Young_Beng featuring Alyssa Black | Toronto |

Buildings that are occupied become more challenging for those wanting to pursue entry.  There is usually some sort of security to contend with before or upon entry.  Then to be able to ride the elevator, an access pass must be swiped to continue up and lastly there are often cameras within the elevators, stairwells and hallways.  In most occurrences those who tend to blend in with the occupants of the building, won’t be as easily targeted as a trespasser.

The rooftopping community is currently predominately male but female urban photographers are increasingly infiltrating the same locations.  Due to the still sexist mentality, females in general do not appear to be as suspicious when trying to enter such locations.

roof parking 2 (1 of 1)
Image taken by Alyssa Black | Toronto |

I have been told that quite frequently when rooftoppers enter into a building they are wishing to climb and attempt to blend in, they have automatically been thrown out.  Oftentimes, they are caught within the stairwells that are well equipped with cameras.  Many rooftoppers have learned that these camera are closely monitored after the fact.  In like instances, a few minutes after beginning to ascend,  the doorway to the stairwell will forcefully thrust open.  A security guard will enter and attempt to enforce their authority by uttering in their most intimidating tone, “are you a guest here?”

roof dome (1 of 1)
Image taken by Alyssa Black | Rooftop 54th Floor | Toronto |

When the trespasser’s retort is nothing more than an, “ummm” they are promptly escorted off the premises.  Feasibly, this is not the first time the security has encountered trespassers with equivalent intentions.  The security guards are familiar with rooftoppers trying to gain access to a myriad of buildings.  The security will likely not be taken aback by these uninvited guests.

Image taken by Ronnie Yip |

After I went on my first rooftop excursion as I disclosed in, “Rooftopping – Part 1:  The Beginning”, I was inspired to vanquish once again with the desire to capture plentiful more images.  I was determined to try my luck by asking a frequent rooftop photographer if I could join him on his next venture.  This particular rooftopper is superior and highly respected within the Toronto urban photography community.  His work is fantastic to say the least.

roof down (1 of 1)
Image taken by Alyssa Black |

He agreed to have me and a friend tag along.   To my surprise the building we were going to climb was one of the tallest buildings in Toronto.  Similar to my first experience, we walked i nto the building following close behind a resident.  Once we entered we waited for the elevator alongside them.  In this particular building it was necessary to have a key card to access the elevator.  We graciously let the tenants swipe their card and push their floor.  The building stands over 80 stories high so we hoped that the floor we would be exiting on would be at a great elevation.  Unfortunately, our unlucky number happened to be the 32nd floor.  This meant we had to climb the remaining 50 floors to reach the top.

daniel lau
Image taken by Daniel Lau |

Once we arrived at the top,  it was just before sunset and the sky appeared to be in a blaze that particular evening because of the amazing red hues.  There were no doors at the top.  It was apparent they were still constructing the top floors because of all the equipment and materials left behind.  There were surrounding metal railings but no windows or glass so the view was completely unobstructed.  The view was clear 360 degrees around soaring at 82 stories high.

We were spooked when we heard someone overhead shout down to us, “Did you hear any security?”  They were perched atop a scaffolding at least another two stories high.  We told them it appeared to be safe and immediately after everyone went back to minding their own business.

roof b&w (1 of 1)
Image taken by Alyssa Black | View from the 82nd Floor | Toronto |

As the night progressed we were joined by three other rooftop photographers.  I would have never thought that 82 stories high up would be a mecca for so many photographers.

At one point of the evening I delicately walked over to the other side of the building.  I was standing under a crane that was situated about another three stories in the night sky.   Once I was under I heard someone yell down to me, “Hey!  You coming up here?”  I peered up but was not able to see who was trying to encourage me to join them.  All I could see was a blazing light that was impairing my vision. The only thing I could think to say was, “No thanks, not this time.”

Vitaliy Raskalov | Hong Kong |

I would have never believed that we spent a total of four hours on the roof taking photos because the time passed by unquestionably  speedily.  There is something truly peaceful being above the busy city shooting from soaring heights down.  The uneasiness involved with getting to the top of this towering skyscraper when you get behind the lens almost immediately escapes your mind.  It is quite an exhilarating feeling.

roof parking (1 of 1)
Image taken by Alyssa Black | Rooftop Parking Lot | Toronto |

Within the rooftopping community some are willing to share the information they obtained through patience and perseverance in regards to what building is accessible and how.  The die-hard rooftoppers will seek the places that are uncontaminated by other rooftoppers.   Meanwhile, the less adventurous will tend to attack a building that are easily identifiable by looking at fellow photographer’s images online.  The novice rooftoppers would prefer to piggyback a location that has already been conquered many times by others.

Image taken by Ronnie Yip | Toronto |

A friend of mine, (I will call her Chloe to keep her anonymity) is not an avid rooftopper but was curious to explore.  She wanted to grasp what all the hype was about.  She would enter into buildings much like the previous instances.  In her experiences, she often encountered buildings with lounge areas or pools situated on the top floors.  Within this environment she was able to blend in with the other patrons and easily photograph the city relatively unnoticed.

Chloe communicated that it did not leave her feeling as if she was doing anything erroneous when she encroached a generally populated area.  She would attempt to access the highest point of the building but was often disappointed when she discovered the door locked.  She was adamant about not willing to break any locks or doors for the tradeoff of a few great images.  It is quite routine that some rooftoppers are willing to break, cut or pick locks in order to reach their desired destination.  On the other hand, many rooftoppers are against this.

tom ryabol
Image taken by Tom Ryaboi | Toronto |

One night Chloe was told by a fellow rooftopper about a building that was easily accessible.  Once again, like many of the other instances she entered into the building along with some residents.  In this particular building, the roof was again locked.  However, the penthouse appeared to still be under construction. She decided to try her luck and proceeded to open the door.  To her astonishment the doors were left unlocked and when she entered, the dwelling appeared to be move-in ready.  There was running water, the electricity was functioning and there was even toilet paper in the bathrooms.

Image taken by Tom Ryaboi | Trump Tower | Toronto |

The whole penthouse floor was unoccupied and all the doors were left unlocked.  Between all three penthouses situated 54 stories high she was able to obtain an unobstructed view of the city from all perspectives.  She went there and shot into the wee hours of the night capturing images from two penthouses.  Without any intention of ever returning, the following night she decided to return to gain access to the other remaining unit and complete the series of images she started the previous night.   Chloe believed that this would be one of her last chances because the tenants would relatively soon be occupying the condos.

notre dame raskalov
Image taken by Vitaliy Raskalov | Notre Dame Cathedral | Paris |

I have been told that once the rooftoppers have gained access and entered these buildings leaving with their desired images they do not look back and have any sense of guilt.  Most are not damaging any property and are respectful enough to leave things as they were found.

The thrill of rooftopping depends on the eagerness someone is  willing to risk in order to leave with an exclusive photograph.

PS. Remember this is supposed to be an informative blog post NOT a how-to.

Until next time,


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Images taken by the following: 

  • Vitaliy Raskalov & Vadim Makhorov

  • Young Beng

  • Tom Ryaboi *featured image

  • Ronnie Yip

  • Daniel Lau