Four hours in Toronto

Start outside Canada’s largest supermarket chain, Loblaws, on Portland Street and Queen Street West. Here, the developer has respected the local area by having shops at street level, echoing the smaller-scale retail on Queen Street West – the supermarket is on the upper floor and Winners fashion store on the next level up. Inside, despite being new-build, there’s a slight industrial warehouse feel that fits with the general area. Before you turn west, look at the painting of a giant eye on a building further east on the south side of the street. The mural is by US artist Shepard Fairey, best known for his Hope poster of Barack Obama created during the 2008 US elections. The building used to house a popular nightclub called Tattoo.

Queen Street West was the baseline established by the Royal Engineers when they laid out the town of York (now Toronto) in 1783. Formerly Lot Street, it was renamed in the 1840s in honour of Queen Victoria. Despite being a heritage conservation area, it is an important east-west corridor with streetcars running along it. Cross the road and head north on Ryerson Avenue, past the new Workplace One, an example of the district’s former factories and warehouses which are now loft apartments or workspaces. Check out Theatre Passe Muraille, located in the former Nasmith Bakery and Stables. One of the city’s top independent theatres, in January it is showing Suitcase/Adrenaline, a production about the experiences of Syrian refugees. passemuraille.ca

Ryerson Avenue is a street of humbly constructed houses that shows the effect of original city planning, which stopped buildings away from the main streets from being higher than three storeys. It also has conservation park areas, where, season permitting (in winter they tend to hibernate), you might see distinctive black squirrels running along telephone wires and electricity cables. These are in fact called the Eastern Grey, but those with black fur dominate. Various explanations have been put forward for their colour, from the presence of black asphalt on roofs, meaning they are more camouflaged from hawks, to the fact that black fur provides more insulation in harsh winters. The mutant gene may also be down to greater levels of testosterone – the black squirrels are more successful at breeding than their grey brothers. You have to be aggressive to survive in the city.

Head up through Alexandra Park, which was created from the gardens of a now demolished house and expanded in the 1960s as the city knocked down old properties and built new ones in the hope of regenerating what was a working class area. The communities themselves have formed local groups and engendered the sense of neighbourhood spirit that is tangible here. You’ll see gardens in schools where pupils grow vegetables and herbs, while at Market 707 you can try a range of street food. Founded in 2010 by the Scadding Court Community Centre, who got the idea from a trip to Ghana to turn old shipping containers into vending stalls, it serves up international food (Japanese, Afghan, Thai, West Indian) as well as local specialities. It’s located on Dundas Street, which was named after Henry Dundas, the first Viscount Melville, who never even visited Toronto. scaddingcourt.org/market-707

Head north along Denison Avenue and you’ll enter the Kensington Market area, home to shops and apartments, through Bellevue Square Park – named after a mansion once here that was owned by the influential Denison family. Characterised by Victorian-era houses, this area has been multicultural for well over a century, settled by the English then, in turn, Russian and Polish Jewish communities, and waves of new immigrants from Italy, the Caribbean, Latin America and Asia. Currently the district faces a challenge from Airbnb, hence the signs about the area being “more than a one night stand”.

It’s a great place for sampling a range of cuisines inexpensively, (try Rasta Pasta for Jamaican-Italian fusion or Nu Bugel for Montréal-style bagels with smoked trout) and buying everything from tourist mementos to local cheese. You can also legally buy marijuana in the city from registered outlets, and smoke it in lounges such as Hotbox Café (which missed out on a licence to sell it as these were awarded by lottery).

Tour Guys offers free walking tours: tel +1 647 557 3249; tourguys.ca