Private 2-Hour Walking Crime Tour in Toronto

Exploring Toronto’s Dark Side: A Closer Look at the Private Crime Walking Tour

A recent review of this Private 2-Hour Walking Crime Tour in Toronto highlights a surprisingly captivating way to learn about the city’s lesser-known stories. Led by former detectives, this experience offers an engaging blend of history, intrigue, and local lore, making it a standout for travelers eager to see Toronto through a more gritty, authentic lens.

What we love about this tour is how personalized it feels—you’re walking through the city with guides who bring decades of police experience to life. The stories are detailed and vivid, often with surprising insights you won’t find in typical city tours. Plus, the cost is quite reasonable for such an intimate experience, especially given the customization options and the fact that it’s a private tour.

One thing to consider is that this is a walking tour, so good footwear is essential to comfortably cover the approximate 6,500 steps. Also, as it’s about the darker, more rebellious side of Toronto, some stories are quite intense, which might not be suitable for very young children or sensitive guests. This tour is perfect for history buffs, social detectives, or anyone curious about Toronto’s less-polished stories.

Who Is This Tour Best For?

If you’re interested in urban history, social issues, or true crime stories, this tour will hit the mark. It’s ideal for locals wanting a new perspective on their city, or visitors who love exploring authentic, off-the-beaten-path narratives.

Good To Know

• Personalized experience: Private tour means your group gets tailored insights.
• Authentic stories: Led by former detectives, offering insider knowledge.
• Walking adventure: Expect to walk around 6,500 steps, so comfy shoes are a must.
• Rich historical scope: From riots to infamous crimes, Toronto’s darker past is laid bare.
• Flexible and customizable: Tours can be adapted to suit your interests.
• Great value: For just over $28 per person, you get an engaging, intimate look at Toronto’s social underbelly.

The Itinerary: What You’ll See and Learn

Stop 1: CF Toronto Eaton Centre

The tour kicks off at the Eaton Centre, with a story from 1977 about the murder of a 12-year-old shoeshine boy. The incident shocked the city but also spurred efforts to clean up downtown, blending crime history with urban development. Reviewers note that this story offers a glimpse into Toronto’s social issues of the time.

Stop 2: Yonge Street

Here, a tragic tale from 2005 unfolds—the murder of a 15-year-old caught in gang violence on Boxing Day. The guide explains how gun violence has left its mark on Toronto, serving as a stark reminder of the city’s ongoing issues with gang-related crime.

Stops on Yonge Street & Beyond

Multiple stops on Yonge Street reveal riots from the 19th century to recent years, including the G20 protests of 2010. These stories help you understand how civil unrest has shaped Toronto’s social fabric. Our guide shared that these riots are not just distant history but part of the ongoing conversation about social justice and policing.

The Path: Social Issues & Mental Health

Moving to The Path, the focus shifts to how mental illness intersects with the criminal justice system, giving a sobering view on social care and law enforcement’s role in mental health treatment.

Downtown & Old Toronto: Legendary Crimes & Mysteries

One of the most popular stops is the story of Ambrose Small, a wealthy theatre owner who disappeared in 1919, sparking Toronto’s greatest unsolved mystery. The guides told us that theories still swirl about his disappearance, making this a fascinating tale of greed, secrecy, and urban legend.

At Courthouse Square, we learn about Canada’s last public gallows and the bizarre crimes that once warranted capital punishment—ranging from cattle theft to stealing turnips. This illustrates how penalties and crime have evolved over the past century.

The Infamous Boyd Gang & Other Notorious Figures

The guides shared that the Boyd Gang’s bank robberies and jailbreaks captured media attention and public imagination. Their escapes from The Don Jail—twice!—are a testament to Toronto’s colorful criminal history.

St. Lawrence Market & The Village

Stories from the early 19th century, like the Jarvis Duel of 1817, show Toronto’s penchant for dramatic, often deadly disputes. Later, stories of the first gangland slayings in 1939 give insight into organized crime’s early foothold in Toronto.

Unique Historical Incidents

One unusual tale involves a riot between circus clowns and firemen in 1855, which led to police reforms still in place today. This quirky story underscores how odd events can have lasting social impacts.

Ghosts of the Past & Modern Mysteries

The tour also touches on ghostly tales from Gooderham & Worts distillery, and the story of a serial killer targeting gay men in The Village, highlighting Toronto’s hidden dark corners and social challenges.

The Distillery District

The tour concludes at the Distillery Historic District, where stories of bootlegging during Prohibition and ghostly legends add a supernatural twist to the tour. The district’s transformation from a gritty manufacturing hub to a trendy district is woven into the story, reflecting Toronto’s evolving character.

What Makes This Tour Stand Out?

Expert guides: Both Jennifer and other reviews praise guides like Phil and Bob for their wealth of police experience, which lends authenticity and detail to every story. They don’t just recite facts—they bring stories to life with anecdotes and insider insights.

Rich, local detail: The stories aren’t just surface-level; they include social issues, legal changes, and historical context that help you understand the city’s development. For example, learning about the last public gallows or the bizarre crimes involving cattle thefts makes history feel tangible.

Authentic, off-the-beaten-path stories: Our review confirms that many of the tales are unique to this tour. From the disappearance of Ambrose Small to the gangland slayings, every story feels like uncovering Toronto’s hidden secrets.

Value for price: At $28.21 per person, the tour offers excellent value for a private experience led by experienced guides. It’s a more intimate alternative to typical city sightseeing, perfect for those who want depth and authenticity.

Customization and flexibility: The tour can be tailored to interests or needs, making it a good choice for groups with specific curiosities or sensitivities.

Practical Details & What You Should Know

Duration: Just over 2 hours, with walking involved, so wear comfortable shoes. Reviewers mention covering roughly 6,500 steps, which is manageable but not leisurely.

Start point: 250 Yonge St, right in downtown Toronto, with easy access to public transit. Ending at the Distillery District makes for a scenic conclusion.

Private experience: Only your group participates, which means stories are tailored to your pace and interests—no crowded bus or group.

Weather considerations: As an outdoor tour, bad weather might affect the experience. If canceled due to weather, a different date or full refund is offered.

Booking & cancellation: Confirmed immediately upon booking, with free cancellation up to 24 hours beforehand, offering peace of mind.

Suitability: Most travelers who can walk comfortably and are interested in social history, crime stories, or local legends will find this tour engaging.

Final Thoughts: Who Should Consider This Tour?

This crime-focused walking tour in Toronto offers a rare glimpse into the city’s shadowy past, perfect for those curious about social issues, historical mysteries, or urban crime stories. Led by former police officers, the stories are detailed and authentic, providing insights that go beyond typical city tours.

History buffs, social detectives, or locals wanting a different perspective on Toronto will find this tour both entertaining and enlightening. The intimate, private setting ensures you get focused attention and personalized storytelling, making it a worthwhile investment for anyone wanting an in-depth look into the city’s darker side.

If you’re prepared to walk and curious about the stories behind Toronto’s most infamous crimes and mysteries, this tour will keep you engaged from start to finish.

FAQ

Do I need to bring anything particular?
Just your comfortable shoes and perhaps some water, especially on warm days. Everything else, like fees and taxes, are included.

Is this tour suitable for children?
The stories are quite intense and involve crime and social issues, so it might be better suited for teenagers and adults.

Can I customize the tour?
Yes, the private tour can be tailored to your interests or needs, making it flexible for different groups.

How long is the walk?
Expect to walk around 6,500 steps over about two hours, so wear appropriate footwear.

What’s the starting point?
The tour begins at 250 Yonge St, in downtown Toronto.

Where does the tour end?
It concludes at the Distillery Historic District, a scenic area perfect for exploring afterward.

Is it accessible for all?
Most travelers can participate as long as they can walk for 2 hours. Service animals are allowed.

What if the weather is bad?
If canceled due to weather, you’ll be offered a different date or a full refund.

How far in advance should I book?
Booking early is recommended to secure your preferred time, especially since it’s a private experience.

What makes this tour unique?
The combination of expert guides with police backgrounds and stories that cover over two centuries of Toronto’s criminal history makes it stand out.

This tour offers an impressive mix of history, mystery, and social commentary, all wrapped up in an engaging walking experience. Whether you’re a history lover, a social critic, or just someone looking for a different way to see Toronto, this tour delivers a fascinating journey into the city’s lesser-known stories.