City’s Oldest Landmarks History Walking Tour of Toronto

1 Review |

Recommended by 100% of reviewers

| Toronto, Canada

2 hours (approx.)

Mobile ticket

Offered in: English

Instant confirmation

Overview

Discover Toronto's rich history on a guided walking tour that takes you to the city's most significant historical landmarks.

Visit the oldest church, the oldest school, the oldest post office, the oldest theatre company, the oldest public market, and a historic brewery that was once the largest in the world.

See the Don Valley Brick Works, Little Trinity Church, Enoch Turner Schoolhouse, and the Alumnae Theatre, formerly Firehall No. 4. Pass by the Globe and Mail Centre, Kings Court, Toronto’s First Post Office, St. Lawrence Hall, and the Omni King Edward Hotel.

Stroll through St. Lawrence Market and David Crombie Park before ending your tour at the Distillery Historic District.

- Discover the rich history of Toronto on a guided walking tour
- Visit the city's oldest church, school, and post office
- Explore the Distillery District and learn about its past
- See the oldest public market and a historic brewery
- Learn about the history of the biggest city in Canada

What's Included

Admission fee
An experienced local guide

Meeting Location

Meeting point

417 King Street East
Toronto, ON M5A 1L3, Canada

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

Distillery District
Toronto, ON M5A, Canada

The ending point is at the Distillery District, just a 5-minute walk from the starting point (Little Trinity Church).

What To Expect

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Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.

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Little Trinity Church

On this stop, we’ll visit Toronto’s oldest surviving church. You will see its striking 60-foot bell tower and the beautiful red and yellow brickwork, hand-molded by 19th-century local craftsmen.As you stand outside this historic site, your guide will reveal the radical history of "The Poor Man’s Church," founded in 1842 as a free place of worship for working-class families who rejected the wealthy tradition of renting pews. You will also view the outdoor cenotaph, honoring the local parish volunteers who served in the Great War, giving you a deep connection to the enduring, community-first spirit of early Corktown.

10 minutes Admission Ticket Free

Enoch Turner Schoolhouse

Just steps from the church, you will find Toronto’s oldest standing school building. You'll admire this beautifully preserved Gothic Revival gem, designed by the same architect, Henry Bowyer Lane, featuring its classic pointed-arch windows and historic brick facade.Your guide will share the story of Enoch Turner, "the benevolent brewer," who established this site in 1848. You will learn how he bypassed the city to build Toronto's very first free school, giving working-class Irish immigrant children access to education. We'll discuss its incredible survival story, from serving as a Great Depression soup kitchen to narrowly escaping the wrecking ball in the 1960s.

10 minutes Admission Ticket Free

Alumnae Theatre Company

At this stop, we will pause outside 70 Berkeley Street, a striking Edwardian Classical structure built in 1905 as Firehall No. 4. You'll admire the bold red brick, arched gables, and the distinctive shortened hose-drying tower that served Toronto's industrial east end for decades.Your guide will share how this heritage landmark was saved from demolition in 1972 by a pioneering, all-female theatre company founded in 1918. You'll discover how they transformed the abandoned fire station into a vibrant cultural hub, and we will share a few spine-chilling stories about the friendly resident ghost rumoured to haunt the stage and tower.

10 minutes Admission Ticket Free

The Globe and Mail Centre

At this stop, we trade the 19th century for the modern day at 351 King Street East. You will look up at the sleek glass tower of the Globe and Mail Centre, designed by Diamond Schmitt Architects, which stands as a symbol of contemporary Canadian national storytelling.Your guide will transport you back to 1844, when the legendary newspaper was founded nearby by Father of Confederation George Brown. You will learn how this block, once nicknamed "Newspaper Row" because of the thunderous steam-powered printing presses, shaped early Canadian identity. We will also step inside the lobby to view historic archaeological artifacts excavated from the site, connecting the digital present directly to Toronto's deep pioneer past.

7 minutes Admission Ticket Free

Toronto's First Post Office

At 260 Adelaide Street East, you will visit a modest brick and limestone building built in 1833. This is Canada’s oldest surviving purpose-built post office and one of the best-preserved links to the colonial roots of the city. You will notice the thick, tooled limestone foundation, built to survive both time and early flooding from the nearby Don River.Your guide will share how this site served as the first connection to the outside world for the young town of York. You will discover how early mail arrived only once a week by horse-drawn stagecoach. We will discuss its history as a customs house and a magistrate's office, and learn about its current life as a museum where visitors can see early postal artifacts from a time when communication required deep intention.

10 minutes Admission Ticket Free

St Lawrence Hall

At this stop, you will stand before a stunning Renaissance Revival masterpiece built in 1850. You will admire its elegant sandstone facade, grand Corinthian columns, and the historic clock tower crowned by a domed cupola and a massive copper bell.Your guide will share how this landmark rose from the ashes of the Great Fire of 1849 to become Toronto’s premier public gathering place. You will hear stories of the historic figures who spoke and performed here, including prime ministers, international singers, and abolitionists hosting rallies in support of the Underground Railroad. You will also learn how a passionate preservation movement saved this magnificent hall from demolition in the 1960s, keeping the cultural heartbeat of early Toronto alive.

10 minutes Admission Ticket Free

The Omni King Edward Hotel

At this stop, you will stand before Toronto's first true luxury hotel, opened in 1903 and affectionately known as the "King Eddy." You will admire the grand Beaux-Arts exterior designed by George W. Gouinlock, a masterpiece built to usher in a golden age of glamour, complete with the city's very first hotel elevators.Your guide will share the legendary stories of royalty and celebrity guests who have graced these halls, from Queen Elizabeth II to Hollywood icons like Elizabeth Taylor and Richard Burton. You will hear about Harry Houdini performing in the spectacular Crystal Ballroom, Ernest Hemingway holding court in the café, and how this social and political hub was saved and restored to seamlessly blend its opulent past with modern luxury.

10 minutes Admission Ticket Free

St. Lawrence Market

At this stop, you will experience the living, breathing heart of Toronto's culinary history. You will explore the iconic red-brick South Market building and see the striking glass atrium of the newly reopened North Market, which seamlessly blends modern architecture with over two centuries of heritage.Your guide will reveal how this site, established in 1803, once served as Toronto's first city hall, police station, and jail all in one. You will learn how the market survived fires and redevelopment to become what National Geographic named the best food market in the world. As we wander, you will discover the multigenerational family stalls that tell the story of Toronto's evolution from a tiny colonial outpost into a bustling, multicultural metropolis.

10 minutes Admission Ticket Free

The Esplanade

At this stop, you will stroll through a lush green corridor that serves as a peaceful escape in the heart of the historic cityscape. You will walk along winding, tree-lined pathways and take in thoughtfully designed sightlines that reach toward the water, reconnecting the urban grid back to its natural heritage.Your guide will share the remarkable story of how this entire park stands on reclaimed land that was once part of Lake Ontario. You will discover how this area transformed from a gritty 19th-century industrial waterfront of railways and factories into a people-first neighbourhood. We will discuss the legacy of David Crombie, Toronto’s beloved mayor of the 1970s, whose vision proved that modern cities can be built for community instead of just cars and commerce.

10 minutes Admission Ticket Free

Distillery District

Your tour concludes in North America’s largest and best-preserved collection of Victorian industrial architecture. Walking along pedestrian-only cobblestone streets, you will admire the towering red-brick structures, arched windows, and historic malting towers of the massive 13-acre complex, including the iconic Stone Distillery built in 1861.Your guide will share the dramatic rise of Gooderham and Worts, which started as a humble flour mill in 1832 and grew into the largest distillery in the world, exporting whisky globally. You will learn how the site survived Prohibition and eventually transformed in 2003 from a closed industrial plant into a vibrant cultural village. We will explore how these historic spaces were repurposed into modern art galleries, theatres, and restaurants, while serving as a famous back-drop for over 800 film and television productions.

12 minutes Admission Ticket Free

Show 9 more stops

Additional Info

Confirmation is instant and will be received at time of booking
Service animals allowed
Public transportation options are available nearby

Suitable for all physical fitness levels
This tour/activity will have a maximum of 40 travelers

Frequently Asked Questions (8)

Q: What is the cancellation policy for the City’s Oldest Landmarks History Walking Tour of Toronto?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

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Activity code: C-5676079P1

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Some states do not allow the exclusion of implied warranties or limitation of liability for incidental or consequential damages, which means that some of the above limitations may not apply. In these states, each party’s liability will be limited to the greatest extent permitted by law.

“AS IS” and “AS AVAILABLE” Disclaimer

The Service is provided to You “AS IS” and “AS AVAILABLE” and with all faults and defects without warranty of any kind. To the maximum extent permitted under applicable law, the Company, on its own behalf and on behalf of its Affiliates and its and their respective licensors and service providers, expressly disclaims all warranties, whether express, implied, statutory or otherwise, with respect to the Service, including all implied warranties of merchantability, fitness for a particular purpose, title and non-infringement, and warranties that may arise out of course of dealing, course of performance, usage or trade practice. Without limitation to the foregoing, the Company provides no warranty or undertaking, and makes no representation of any kind that the Service will meet Your requirements, achieve any intended results, be compatible or work with any other software, applications, systems or services, operate without interruption, meet any performance or reliability standards or be error free or that any errors or defects can or will be corrected.

Without limiting the foregoing, neither the Company nor any of the company’s provider makes any representation or warranty of any kind, express or implied: (i) as to the operation or availability of the Service, or the information, content, and materials or products included thereon; (ii) that the Service will be uninterrupted or error-free; (iii) as to the accuracy, reliability, or currency of any information or content provided through the Service; or (iv) that the Service, its servers, the content, or e-mails sent from or on behalf of the Company are free of viruses, scripts, trojan horses, worms, malware, timebombs or other harmful components.

Some jurisdictions do not allow the exclusion of certain types of warranties or limitations on applicable statutory rights of a consumer, so some or all of the above exclusions and limitations may not apply to You. But in such a case the exclusions and limitations set forth in this section shall be applied to the greatest extent enforceable under applicable law.

Governing Law

The laws of the Country, excluding its conflicts of law rules, shall govern this Terms and Your use of the Service. Your use of the Application may also be subject to other local, state, national, or international laws.

For European Union (EU) Users

If You are a European Union consumer, you will benefit from any mandatory provisions of the law of the country in which you are resident in.

United States Federal Government End Use Provisions

If You are a U.S. federal government end user, our Service is a “Commercial Item” as that term is defined at 48 C.F.R. §2.101.

United States Legal Compliance

You represent and warrant that (i) You are not located in a country that is subject to the United States government embargo, or that has been designated by the United States government as a “terrorist supporting” country, and (ii) You are not listed on any United States government list of prohibited or restricted parties.

Severability and Waiver

Severability
If any provision of these Terms is held to be unenforceable or invalid, such provision will be changed and interpreted to accomplish the objectives of such provision to the greatest extent possible under applicable law and the remaining provisions will continue in full force and effect.

Waiver
Except as provided herein, the failure to exercise a right or to require performance of an obligation under this Terms shall not effect a party’s ability to exercise such right or require such performance at any time thereafter nor shall be the waiver of a breach constitute a waiver of any subsequent breach.

Translation Interpretation

These Terms and Conditions may have been translated if We have made them available to You on our Service.

You agree that the original English text shall prevail in the case of a dispute.

Changes to These Terms and Conditions

We reserve the right, at Our sole discretion, to modify or replace these Terms at any time. If a revision is material We will make reasonable efforts to provide at least 30 days’ notice prior to any new terms taking effect. What constitutes a material change will be determined at Our sole discretion.

By continuing to access or use Our Service after those revisions become effective, You agree to be bound by the revised terms. If You do not agree to the new terms, in whole or in part, please stop using the website and the Service.