Walking Tours of Toronto’s Past

Put on your walking shoes and travel back through time with HistoricTO.

How much do you really know about Toronto? Did you know that Sunnyside Pavilion was the hotspot back in the 1920s or that Toronto’s first mayor fought against social and political oppression? The city’s origins, cultural heritage and local history run deep through these streets.

The Toronto you know today has vastly changed and now you can revisit its past thanks to the City of Toronto’s new program, HistoricTO. Spotlighting the city’s history museums, HistoricTO offers timed-ticketed walking tours that are neighbourhood-centric and cover a variety of topics from colonization to urban development to immigration, and more. 

The program runs until September 4th and tickets must be purchased in advance on a pay-what-you-can donation basis. Tours are one hour in length and vary in content, allowing participants to explore Toronto through a historical lens that covers its colourful past.

Rest assured that HistoricTO’s walking tours follow the health and safety guidelines provided by Toronto Public Health COVID-19 Guidance for Cultural & Heritage Institutions and Attractions. 

Rewind 100 years with Colborne Lodge (11 COLBORNE LODGE DR.)

Inside Colborne Lodge at High Park in Toronto
Colborne Lodge was the home of John and Jemima Howard, whose land was left to the City of Toronto and is now known as High Park

Sunnyside Pavilion and Lakeshore’s boardwalk make up one of the most popular outdoor areas in Toronto, especially during sweltering summer days. The sprawling beaches, shaded trails and massive public pool render this west-end location a summertime mecca. 

Time-travel back 100 years and you’ll see that things weren’t so different. In fact, Sunnyside was a hotbed of festivities and gatherings because it was accessible to all, regardless of class and ethnic origin.

Explore Sunnyside and Lakeshore’s heyday with Colborne Lodge’s Walking Tour, and dive deep into the political, social and natural landscape of the area. The tour begins at Colborne Lodge and ends at High Park’s Grenadier Pond. Keep in mind that this 60-minute walk takes place on uneven surfaces with some hills and limited seating. 

Awaken to the hard truths of Battle at Fort York (250 FORT YORK BLVD.)

Fort York National Historic Site visitor centre
Fort York is home to Canada’s largest collection of original War of 1812 buildings

Most Torontonians know very well about the War of 1812, whether through school or having visited Fort York at some point in their lives. And if you don’t, then this Fort York National Historic Site Walking Tour is a great place to start—or to freshen up your current historical knowledge. Because what many don’t know is how the war impacted the Indigenous and Black populations at the time.

Throughout this 60-minute tour, listen to detailed stories about how disadvantaged communities fought to defend York (Toronto) and Upper Canada. Within Canada’s largest site of the original War of 1812 buildings, you’ll get first-hand knowledge through military records, letters, memoirs and oral accounts.

Play historical telephone with Gibson House Museum (5172 YONGE ST.)

Nowadays, Willowdale is a family-centric neighbourhood in Toronto’s North York. Two hundred years ago, it was a postal village with lots of stories to tell. Some more dramatic than others. This 60-minute walking tour begins at Gibson House Museum, once the home of David Gibson, a first settler from Scotland, farmer, politician and later on, rebel and escapee.

Listen to retellings of the Upper Canada Rebellion of 1837 and the evolution of North York, wherein details change from storyteller to storyteller. Learn about the heroes, rebels and reformers of that pivotal time in Toronto’s history.

Educate yourself on systemic racism with Mackenzie House (82 BOND ST.)

Located in the downtown core, just steps from the Eaton Centre and Yonge-Dundas Square is Mackenzie House, a heritage site rich in history and the starting point of this 60-minute walking tour. Home to Toronto’s first mayor, William Lyon Mackenzie, this walk explores his personal rebellion against Toronto’s unethical and ruling elite, while also touching on the political and cultural landscapes of his time (1800s).

Learn detailed accounts of how disadvantaged groups including impoverished Irish immigrants, enslaved Black communities and how desperate First Nations fought back against crooked policies and won, paving the way for the Toronto we know and love.

Experience Toronto in technicolour with the Market Gallery (95 FRONT ST. E.)

The Market Gallery at St. Lawrence Market
The Market Gallery on the second floor of the South St. Lawrence Market is all that’s left of Toronto’s original 19th-century Front Street City Hall council chamber

You’ve seen it on Instagram and it’s probably caught you by (pleasant) surprise while commuting through the city—Toronto’s mural art is some of the best in the world. Explore it in detail with The Market Gallery Walking Tour. This 60-minute walk showcases the ways in which artists transformed Toronto’s streets and laneways into an urban art gallery. Enjoy more than 100 StreetARToronto (StART) projects from 2012 to 2019.

This tour begins at The Market Gallery, an art space dedicated to the art, culture and history of Toronto, located on the second floor of St. Lawrence Market.

Meet the 200-year-old patrons of Montgomery Inn (4709 DUNDAS ST. W.)

Montgomery Inn Museum is one of Toronto’s most striking buildings, inspired by Roman and Greek architecture. In its prime, the Inn was a popular community centre that served as a hub for locals who needed shelter, food and drink, or just laughs with friends. It was a safe space for townspeople, including the Indigenous population and settlers, to kick back and share stories during Etobicoke’s development era.

Explore the Inn’s grounds around Thomas Riley Park and Mimico Creek, while learning about the historical impact of significant personalities that traversed the inn. The Montgomery Inn Museum Walking Tour is 60-minutes long, with some sloped and grassy areas.

Uncover hidden history with Scarborough Museum (1007 BRIMLEY RD.)

Exterior of Scarborough Museum and surrounding gardens
Located in Thomson Memorial Park, Scarborough Museum offers a glimpse into the life of early settlers

Along the walking trails of Thomson Memorial Park in the east end of the city, sits Scarborough Museum. The Scarborough Museum Walking Tour explores hidden, untold stories of events that shaped the current Scarborough community. This neighbourhood has a complex colonial history, and in 60 minutes you’ll engage in crucial conversations that deconstruct its past.

Learn about Scarborough’s growth, from its inception to its rise, cementing itself as a major suburb of the 20th century. Most importantly, look ahead to the city’s future and where it’s headed from here.

Live through the early 1900s with Spadina Museum (285 SPADINA RD.)

Spadina Museum, or locally known as Spadina House, is a breathtaking testament to a time of dramatic social change. Until the 1930s, this gorgeous estate with famously manicured gardens belonged to James Austin, founder of the Dominion Bank. Today, Spadina Museum is widely known for its Gatsby-themed garden parties, but back then it was a symbol of prosperity during a time touched by WWI, the Great Depression and Canada’s own social tensions.

Embark on this Spadina Museum Walking Tour, with neighbourhood stops around the grand estate. For 60 minutes, explore past societal and political climates around the Davenport escarpment and how it affected the wealthy versus Indigenous population. Learn about the Austin Family and how they impacted Toronto’s financial, business and cultural evolution. Please note that this tour includes descending steps and a sloped road.

Learn the secrets of the Don River at Todmorden Mills (67 POTTERY RD.)

Painting of Todmorden Mills in Toronto
Set in the Don Valley, Todmorden Mills explores the history of Toronto’s industrial growth

The Don River Valley is a great area for biking and hiking, but not so much for swimming. In fact, it’s probably not recommended. The river’s lack of purity is a result of Toronto’s urban expansion, dating all the way back to its first settlers. In recent years, the city has been making strides in cleaning up the waterway and improving its quality.

However, eleven thousand years ago, the Don Valley was a bountiful land, prime for hunting and gathering. This fruitful area drew in Indigenous Tribes, specifically because of its rich waterway that brimmed with marine life.

The Todmorden Mills Walking Tour takes you on a ten thousand year journey through the Don Valley, from its untouched purity to settlers harnessing its power while building the young city of York (Toronto). During this 60-minute tour, learn about the environmental effects of the Industrial Revolution and the current ways in which the city is undoing the damage.  

Discover Toronto history from home 

If you’re unable to participate in a walking tour, or if you’d like to complement your tour experience even further, Toronto History Museums are currently offering online access to their artifact collection. Click through 150 artifacts that include 3,000 works of art, spanning 11,000 years of Toronto history.

See it. Snap it. Share it. In every neighbourhood, around every corner, through every door there's something that begs to be discovered in Toronto.


More Insights & Ideas from Locals

Food & Drink

See & Do

Holidays, Christmas & Winter