Toronto Crime Tours

“The only crime tour in Canada hosted by former detectives”

BOOKING OPENS SPRING 2025

Downtown to the Distillery Walking Tour

2 HOUR TOUR
Length: 4 km / Duration: 2-2.5 hrs / Stops: 15
Tour start: West side of Yonge St opposite 245 Yonge
Tour end: Distillery District (360 Cherry St)
Our original tour with an update! Starting off on world-famous Yonge St, we revisit the 70s, when the downtown core was full of sex clubs, pinball arcades and shady massage parlors, and the murder that shocked the city into cleaning up its sleezy side. We discuss crimes, old and new, including the disappearance of theatre empresario Ambrose Small in 1919 and the G20 riots that tore through downtown streets. We have some lighthearted tales as well, from the Circus Clown riot in 1855 to the bizarre laws that made topless sunbathing illegal – but only for women. We visit The Esplanade, discuss the infamous Jarvis duel in 1817 and the salacious murder of Bert Massey, known as the Trial of the Century, in 1915. We finish in the Distillery District, many years removed from its bootlegging heyday during Prohibition of the 1920s.

CLOSED FOR THE SEASON
Bloor Street West to Graffiti Alley Walking Tour

2 HOUR TOUR
Length: 5.5km / Duration: 2hrs / Stops: 15
Tour start: 351 Bloor St W, S/E corner at Huron St
Tour end: Graffiti Alley (Queen and Bathurst)
Starting at the site that was once Rochdale College (341 Bloor St W), we talk hippie culture and drug laws of that era. Far out! We then walk through University of Toronto, Chinatown, Kensington Market and Trinity Bellwoods.
We end up at Toronto’s famous Graffiti Alley at Queen and Bathurst. You'll hear how laws for same sex marriage and abortion have evolved, The Dirty Tricks Gang, 'Red' Ryan, who was called Canada's Jesse James, Canada's most prolific bike thief, and other strange tales. And did you know there is a Toronto connection to the assassination of Martin Luther King?

CLOSED FOR THE SEASON
Roncesvalles to Parkdale Walking short Tour

1 HOUR TOUR
Length: 2km / Duration: 1 hr / Stops: 7
Tour start: Dundas West Subway Station
Tour end: 1698 Queen St W
Starting at Dundas West station, our first case reveals how a rare door-to-door canvass for DNA swabs led to the arrest of a killer. As we walk down beloved Roncesvalles Avenue (Roncy to locals), we discuss a brazen daylight mob-style hit at a restaurant. We give a nod to nearby High Park with the story of one of Toronto Police’s most interesting Chiefs, Dennis Draper, whose horseback officers were notorious for breaking up political rallies. At a local bank, we talk about an employee who defrauded millions from customers to feed his gambling addiction. At a fruit stand, we share the absurdity of the Lord’s Day Act, which forbade any form of shopping in 1906.

CLOSED FOR THE SEASON

FAQs

How long are the tours?

Our Downtown to the Distillery tour is 4km; Bloor Street West to Graffiti Alley is 5.5km; and Roncesvalles to Parkdale is 2km.

What is your cancelation policy?

You can cancel without penalty at any time for a full refund. However, a cancellation within 24 hours will not be refunded, only a credit for a future reservation will be issued.

What if I use a mobility device?

All 3 tours are spent on either city sidewalks or paved paths in parks. Please note the duration and distance of the tours, you will be walking for 2.5 hours on the long tours and 1 hour on the short tour.

What if it rains?

If there is a potential weather threat (e.g. thunderstorms) we will contact you 3 hours before the tour.

What if I'm late or delayed?

Please reach out to us through our social media accounts if you're running late. In fairness to the other guests, we won't be able to wait too long. You can always catch up to where we are, just send us a message.

Is there a restroom break along the way?

Yes, there are public restrooms on route, if needed. There are also coffee shops everywhere, too. If its a hot day, be sure to bring some water.

Why must I 'sign' a waiver?

Yes, this is a requirement from our insurance provider.

Do you accept tips/gratuities?

Of course, since it is a tourism industry standard, but they are not required. Other options include donating to our 2 charities, which is where a portion of profits and tips will be going: Canadian Centre for Abuse Awareness (www.abusehurts.ca) and Toronto Beyond The Blue, a charity dedicated to mental health for Police Officers (www.torontobeyondtheblue.com)

What about private tours?

We definitely can provide a private group tour for your team building event. Any of our 3 tours can be arranged for a time and day of the week that suits your group's schedule. Family party, promotion, or just exploring this fine city and hear some whacky tales along the way. Please email us (info@torontocrimetours.com) to arrange your private tour.

ABOUT US

Bob and Phil are both life long residents of Toronto. They both started their policing careers in North York in 1987. Phil also worked in Regent Park, and was a Detective in Fraud Squad and Sex Crimes. Bob also worked in The Beaches/Danforth, Parkdale, Transit Patrol, and as a Detective downtown.

Soon after retiring, Bob and Phil realized they missed mingling with the public, sharing stories of how the city changed over their 30 years. This led to looking at changes to the city over it's history from a crime and punishment lens. Thus was born Toronto Crime Tours.

The tours are borne of a love for their city, and a recognition of its growth and evolution, sometimes through tragedies that grip the whole city, but also through quirky and strange events that have taken shape over 300 years. Remember, this is a city that once outlawed tobogganing and petty thievery could lead to the gallows. Come explore the long, varied tales of how Muddy York (Olde Toronto’s nickname) became one of the most coveted cities to live in around the world.