From rooftops, urban explorers have quite a view. 

Caleb Ackerman-Stratton’s rooftop adventures started in primary school when he climbed Wolseley School. As a teenager, he had a rope on his mom’s house to get him and his friends up. Now, he has a ladder leaning against his house to climb to the porch roof. 

“In a city, you’ve always got people around,” Ackerman-Stratton says. 

From the roof, you can get away and take another view of the city. 

It also offers a taste of danger, although he is careful to never go anywhere that will be difficult to climb down from. 

But is it legal? 

“Should someone see an individual(s) on a rooftop and contacted 911 because they felt it was dangerous, emergency personnel would attend. Each incident has different circumstances and would be treated based on those specific circumstances,” a Winnipeg Police spokeswoman said in an email. 

Ackerman-Stratton’s teachers were unimpressed with his childhood expeditions to the roof, but he says he has otherwise never been in trouble for seeking higher ground. 

Jay, who wished not to be identified by his real name, has been caught on rooftops a few times. There were no legal repercussions. He was just asked to leave. 

“I just think it’s fun,” Jay says. He routinely checks if rooftops of buildings he goes into are accessible. 

One of his finds was the accessible roof of a 50-storey building, which was not in Winnipeg. During the day, it gave him a view of the entire city. 

“It’s exciting to be in a place you’re not supposed to be,” Jay says. 

While the potential of being caught can be thrilling, Jay doesn’t get a rush from the physical danger because he doesn’t think of the activity as being dangerous. 

Jay says safety is always relative – bad things can happen anywhere, including on top of roofs and at ground level. 

That’s not to say he hasn’t found himself in unsafe situations. While wandering the roof of one building, he realized it was unsupported. He had to find the support beams and carefully walk to a place where he could get down. 

“The rooftop is not made to be walked on,” Douglas Wiebe, pastor of the Exchange Community Church, says about 75 Albert St. 

Empty beer cans and pipes are evidence trespassers have made their way up to the roof of the church. 

“I cannot fathom the stupidity of people who go up there to drink and smoke,” Wiebe says. People should be in sound mind when in such a dangerous position, he adds. 

Workers going up to the church’s roof aren’t allowed closer than eight feet to the edge without safety harnesses, but trespassers are likely not following that rule. 

In fact, Wiebe has caught people walking along the edge of the roof. 

There have been no accidents on top of the church. To keep it that way, padlocks now prevent urban explorers from making their way to the rooftop on Albert St. 

But nothing stops Ackerman-Stratton and Jay from finding a way up for a new perspective on the city.

Published in Volume 70, Number 4 of The Uniter (October 1, 2015)