Meet The Toronto Tour Guy

We're planning on being pretty drunk tomorrow night. We'll be at the Little Red Umbrella Variety Spectacular, you see, at the Holy Oak Cafe, where 10% of  bar sales are going to support the AIDS Committee of Toronto. So it seems rather appropriate that we'll be kicking off the night with Jason Kucherawy. Not only is he the co-founder of Tour Guys, a company that gives walking tours of Toronto and Vancouver, some of them for free, and one of them called "Beer Makes History Better", but he'll also be talking about prohibition in Toronto - that sad, dry era - and the ways it shaped the city we live in today.

We figured that ahead of tomorrow night's festivities (ahem, Facebook invite here), we'd get him to answer some questions so that you can get to know him a little better.

How did you first start geting interested in the history of Toronto?

I've been interested in history since I was quite young. From about age 9 I was into dinosaurs, ancient cultures like the Maya, and major conflicts like the World Wars and the Vietnam War. I was a regular at the local library as soon as I could ride my bike there on my own. Since I started leading tours of Toronto three years ago I've made that the focus of most of my current reading. My tours aren't all history-oriented, but knowing the history of Toronto is essential for any tour guide who wants to be taken seriously. Having studied anthropology in university I know how important understanding the past is to understanding the present.

How and why did Tour Guys start?

I had been leading tours for other companies, mostly educational tours for students and teachers to other cities, since 1996 (I think - it's been a long time) and when I departed from that industry a few years ago I decided to start my own business. My good friend Steve Woodall in Vancouver and I agreed to start up Tour Guys in 2009 to offer free walking tours of our respective cities. The idea was based on successful tour operators in Europe doing just that. I don't think it had ever been tried in Canada and we figured we would give it a go and see what happened! It was a desire to make a living doing what we loved to do (lead tours and share our passion for our city) that inspired us to start Tour Guys.

What's your most popular tour?

As far as sheer numbers go, our "Toronto Ghost Tour" is the most popular. We've run it for 3 years around Hallowe'en now and just this past year completely re-vamped it to include some possible explanations for what people might think are supernatural experiences. For the tours we offer year-round our "Beer Makes History Better" is a huge hit. I could be wrong, but I think it's the "Beer" in the title that sells people on it. It's one of our "Urban Adventures" which are offered year-round, 6 days a week.

What's your favourite tour to give?

I would say it's a toss-up between "Beer Makes History Better" and our "Kensington Market and Chinatown" tours. Between these two tours, most of my favourite topics are covered: craft beer, Toronto history, graffiti and public art, and multiculturalism. I also like showing off some of the coolest parts of Toronto like Kensington Market's alleys and side streets, St Lawrence Market, and the Distillery District. On both tours I also bring people by some of my favourite places to eat, drink, and hang out.

What do you think is Toronto's best kept historical secret?

I think our best kept historical secret is how harsh life was here even 100 years ago. We didn't have safe drinking water available to the majority of Toronto until the very late 19th century. Disease, fires, violence - there are many things that have happened here most people are unaware of. I sometimes joke on my tours that the 19th century is highly overrated and over-romanticized. If a mad scientist appeared in a time machine and a puff of smoke and invited me back to 1850 I would tell him, "I'll pass thanks. I like shitting in a toilet and showering daily too much."

What do you think is the biggest misconception about the city?

I think the biggest misconception about our city is that we don't really have much history. We might be a young city as far as cities go, but the path we've taken from a small colonial outpost in 1793 to the metropolis of more than 2.5 million today is rife with great stories. I don't think this city does enough to teach its citizens about its history. We don't have a city history museum - a single modern facility - where residents and visitors can go to learn the story of Toronto. For a city this large to not have one, I think we are doing a disservice to our citizens and keeping them ignorant of our past. I'll end my rant there.

What is/are your favourite place/places in Toronto?

I have a long list of favourite places, and what they have in common are great people who work there or collect there. I have my list of pubs, coffee shops, stores, and other haunts I frequent and it all comes down to the people there that bring me back. Being a tour guide, I'm out and about in the city a lot and I've gotten to know a lot of people who run local small businesses that really give Toronto its character. I love walking into an independent coffee shop like Jimmy's, a pub like The Avro, or a clothing store like Glossy Collective, knowing the people behind the counter well enough to call them friends. Most of them do more than just work, they organize fundraisers, they make art, they create connections and form a community, and they all love this city too. Short answer: my favourite place in Toronto is anywhere I'm with others who are just as in love and in tune with this city as I am.


The Little Red Umbrella Variety Spectacular is happening on January 20, 2012, at the Holy Oak Cafe. It starts at 9pm and 10% of bar sales will going to the AIDS Committee of Toronto. You can learn more about it here.

You can check out Tour Guys online here.


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