Toronto street art tour: The neighbourhoods awash with graffiti art and murals

It all started with a kid riding the subways of New York on long hot summer afternoons in the late 1960s. His name was TAKI. Employed as a delivery boy, TAKI one day found himself alone at a station where he scrawled his name and street number, "TAKI183" on a wall for his friends to see. He continued doing so at stations throughout the city.

Fuelled by an element of mystery, a trend soon caught fire, and before long, a simple scrawl had morphed into entire train exteriors being spray painted. Kids would sneak into train depots at night, spray painting through the small hours before gathering at sunrise to see their handiwork roll out of the terminal, a phenomenon known as "benching".

I'm standing in a backstreet of Toronto's Queen Street West neighbourhood with Jason Kucherawy, a tour guide with a passion for all things street culture. There's a light dusting of snow on the ground and as we stand hunched in our puffer jackets, Kucherawy is enlightening me on the origins of graffiti culture.

The question of public space and where to draw the line on freedoms of creative expression has long since been an issue in major cities throughout the world and Toronto is no exception. But in recent years, the city has realised that allowing certain areas to serve as unofficial public art zones has led to an upswing in the quality of "pieces" while decreasing the prevalence of what might more readily be considered vandalism.

Across the street, we head to one such area, dubbed Graffiti Alley. For almost a kilometre, the walls are awash with vibrant colour, a mish-mash of murals, pieces and "throws", the term given to elaborate lettering styles, like a "tag" on steroids.

At first glance, the scene might resemble a free-for-all, but as Kucherawy explains, there is a complex code of honour lurking behind each swirl of paint.

For starters, a new or emerging artist should never cover over the work of someone more established. Highly respected pieces will remain untouched the longest; the overall goal centred around a constant strive for improvement.

New artists often work with more experienced artists to avoid the many potential faux pas of the subculture and even veteran artists will often contact other bigwigs when travelling to avoid similar pitfalls.

"The competitiveness, that's a part of graffiti culture, of hip-hop culture, it's really a way for young adults in the inner city to battle each other without resorting to violence. Whether it's DJ battles, rap battles, graffiti is no different, there's a hierarchy, you try and do things bigger and better," says Kucherawy.


A few minutes further, on the corner of Portland and Queen Streets, we duck into Loblaws Supermarket. Behind the cash register, a garish mural fashioned by Toronto artist, "SKAM" serves as the backdrop to a team of high schoolers bagging groceries.

The piece highlights another division within the graffiti community; those who believe the art form should forever remain subversive, and those who feel using their skills for financial gain is a natural evolution of the movement's increasing gravitation towards the mainstream.

As the tour winds up, we duck into Tequila Bookworm, a former café-cum-bookshop selling the occasional craft beer that's since evolved into a craft beer bar purveying the occasional coffee. We've come to check out more graffiti in the basement but somehow, our conversation on street culture takes over.

Kucherawy's tour stands out for many reasons. On a more obvious level is the payment model; guests need only tip what they feel the experience was worth. But more intrinsically, it's the anthropological approach he brings to the topic; there's a broader passion that links the entwined cultures of fashion, music and breakdancing that leave you ruminating on wider themes long after the tour is over.

Heading back to my hotel, I decide to cut back through Graffiti Alley for another look.

In the bracing late afternoon chill, I pass a handful of teenagers, laughing and posing for pictures in front of murals.

High above them, above the alley and the adjacent lanes of rush hour traffic, a billboard the size of a small football pitch advertises a new hatchback for sale, $25,500, drive away.


Guy Wilkinson was a guest of Tour Guys and Tourism Toronto.



Air Canada flies direct between Sydney and Vancouver with ongoing connections to Toronto. See


The InterContinental Yorkville is a four-star hotel centrally located in The Annex, near Royal Ontario Museum and University of Toronto. See


Tour Guys offers themed tours around Toronto, Vancouver, Ottawa and Hamilton. The Graffiti Tour, Queen Street West is 1.5-hour excursion with guests encouraged to pay what they feel. See