Walking and talking in Canadian cities since 2009
1-800-691-9320
Old Town Toronto Walking Tour
A darkly entertaining dive into Toronto’s chaotic beginnings—duels, plagues, fires and all.
On our tip-based walking tours, you’ll pay a small $6 booking fee (after taxes and fees are added) to reserve your spot. At the end of your tour, you tip your guide whatever you feel the experience was worth—most guests tip $10–$20 per person. Our guides work hard to deliver unforgettable tours, and this model helps keep them accessible to everyone.
Some guides are able to accept PayPal, or may have a credit card reader to accept payment, but do not have Venmo - that's an American payment system only. Cash is best!
90 minutes
On the steps of Toronto's Old City Hall, under the clock tower by the war memorial
1+
$6 booking fee + tip what you feel
Guided walking tour full of entertaining and historical storytelling
⚔️ Hear stories of duels, hangings, horses, and circus clowns
🔥 Learn how fire reshaped Old Town forever
😷 Discover where cholera and smallpox once ran rampant
What to Expect
Step into Toronto’s untamed beginnings. The Old Town Toronto Walking Tour starts on the steps of Old City Hall—a sandstone sentinel that’s seen everything from corruption trials to movie shoots. This 90-minute tour is your passport to a grittier, juicier version of Toronto history. We’ll wind through alleyways and courtyards once patrolled by pickpockets, reformers, and politicians with pockets to pick.
Your guide will walk you past towering churches, gallows lore, and the bones of the city’s original marketplace—all while unpacking how this place grew from colonial outpost to Canada’s biggest city. Hear tales of fire and fraud, civil unrest and cholera, bootlegging and boomtown dreams.
Learn how city hall politics, public hangings, and early multicultural migration all collided in a neighbourhood that still echoes with ambition and chaos. Whether you’re new to Toronto or think you know downtown cold, this tour digs into the stories that rarely make the textbooks but built the city from the ground up. Come for the facts—stay for the scandal.