Take a Toronto Walking Tour

By Mike Friskney

COVID-19 has made it challenging to visit with neighbours but it doesn’t mean you can’t spend some time exploring a new neighbourhood. Many of us have driven through the various neighbourhoods that form Toronto, but very few of us have taken the time to get to know the fascinating history behind each one. Booking yourself on a social distanced walking tour is the perfect way to do this.

To help whet your appetite here are some walking tour suggestions:


The Annex Neighbourhood

The Annex

Back in the 1870s and 1880s, a new Toronto neighbourhood was created whose boundaries were Avenue Road in the east, Bathurst Street in the west, Bloor Street in the south and Dupont Street in the north.  The Annex quickly became the neighbourhood of choice for the elite of elite of Toronto society. We’re talking high rollers like George Gooderham, the man behind Gooderham & Worts whisky, and Timothy Eaton, the head honcho of the once dominant, coast-to-coast Canadian retail chain Eaton’s.

Other points of interest along this high brow hike include cultural institutions such as the Royal Ontario Museum and the Royal Conservatory of Music, plus a stroll through Mirvish Village, an enticing enclave of homes and shops that will delight bookworms, vintage aficionados, art connoisseurs and fashionistas. You’ll explore all this and more on The Annex Tour hosted by Muddy York Tours.


St. Clair & Yonge Neighbourhood

Everyone knows about Casa Loma but it’s not the only historic millionaire’s residence in the Yonge & St. Clair area; no wonder the ridge that runs east west and south of St. Clair is known as Millionaire’s Row.

Sign up for the Casa Loma and Millionaire’s Row tour from Genova Tours and you’ll enjoy a walk and talk featuring the former estate homes of Toronto’s Victoria-era millionaires. Hear stories about these posh palaces and the people who occupied them; striking stately addresses such as Rose Hill, Summerhill, Woodlawn, Oakland, Benvenuto, Russell Hill, Spadina, Davenport and Wycliffe.

Of course, a tour past these grand abodes would not be complete without pausing at Casa Loma, which cost $3.5 million dollars and three years to build back in 1911-14. Led by Bill Genova, a historian and vivid storyteller, this tour will make Millionaire’s Row come alive all over again.


Leslieville-Riverside Neighbourhood

Let’s head back to a time when Toronto wasn’t just home to well-to-do millionaires. In particular, in the 1700s, the Leslieville to Riverside area was where gangs, crooks, heroes and sailors called home. For black slaves escaping the United States, this neighbourhood also stood for freedom as one of the final stops of the Underground Railroad.

Many of the areas’ occupants earned a wage at the Don Valley Brick Works, which operated for almost 100 years pumping out bricks that formed the façade of many of Toronto’s most iconic structures including Casa Loma, Osgoode Hall, Massey Hall and the Ontario Legislature.

As you can see, there are a lot of gritty characters, stories and legends to explore in this neighbourhood, and you can revel in all of it and savour a brewskie or two by signing up for the Leslieville-Riverside History Beer Tour which is led by Ian, a trained actor and professional photographer.


Kensington Market and Chinatown Neighbourhoods

Two of Toronto’s most interesting areas are bordered by Dundas Street—Kensington Market and Chinatown. On this tour, offered by Urban Adventures, you get to discover both.

Back in the 1920s, the Kensington Market neighbourhood was mostly made up of working class Jewish people. Today it is a true reflection of the diversity of Toronto with citizens from Europe, the Caribbean, the Middle East, South America and Asia putting down roots here.

This eclectic mix of people makes for a cornucopia of culture…everything from festivals, vintage shops, coffee shops, cafes, bakeries, bars, street graffiti and, of course, the famous Kensington Market where you can shop for fresh meat, fish and produce.


Next door to the Kensington Market area is Chinatown. One of the largest Chinatowns in North America, its sidewalks continuously buzz with people and activity. Stop at a market and learn about an exotic fruit or vegetable. Pop into shops and discover new spices, teas or a unique electronic gadget. Learn the intriguing history and local stories, and when your tour reaches its conclusion, refuel on authentic Chinese cuisine from one of the restaurants recommended by your guide.


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