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Navigating between the 19th and the 21st century on Isabella

Updated: Feb 20, 2023

WHAT'S IN IT FOR YOU? This walk includes an eclectic cluster of architectural styles + decadent treats.

I had the opportunity this weekend to walk around Isabella Street and I was once again seduced by the urban textures of this unique street where historic houses and modern condos coexist.

Isabella Street covers .83 km from Yonge Street to Sherbourne, which makes for a less than 30 minutes round trip walk (not counting the time to admire the architecture). At the end of this article, I suggest a cool 2.6 km loop to make the most of the area.

Almost immediately as you walk down Isabella Street, you come across the chaotic collage of architectural styles from different eras.

Starting point

Isabella Street is a 5-min walk from the Bloor/Yonge subway station, starting right across from Cheese Baker (690 Yonge Street).

One can't sit in this little Asian bakery, so I took a few interesting items to try at home. The soft pink dragon fruit bun was a hit with my gang. The one made with black bamboo charcoal bread filled with cream cheese and sweet potato was also quite good.

At the corner of Isabelle and Yonge, I admired the red-on-black neon silhouettes from the window of the Chinese restaurant Miss Fu In Chengdu (637 Yonge Street). Their menu looked intriguing. I made a mental note to go back!

Isabella Street

Almost immediately as you walk down Isabella Street, you come across the chaotic collage of architectural styles from different eras. Behind the Artful Dodger (12 Isabella St.), an old Second Empire style pub built in 1910, the modern One Bloor is waving at us. It is Toronto's 2nd tallest condo tower after the Aura... for now.

Across the street, the Victorian flourishes of the beautiful house at number 17 take us back to 1885, contrasting against the simple lines of the surrounding buildings. It was advertised for sale for $5 million at the time of writing.

The ArQuives (34 Isabella Street), dating from 1860, is a rare example of Italianate style in Toronto, which gives it a good chance of survival. At the moment, it grabs housing the largest LGBTQ2+ archive in the world.

Built in 1931, the Brownley Apartments (40-42 Isabella Street), takes a stab at Art Deco. The apartments at 72 Isabella Street were built in 1926 by the Eaton Company to house its employees.

The Victorian beauties at 90-94 Isabella Street are awaiting their historic building designation. Built in 1885 in the Queen Anne Revival style, they will be restored and incorporated into a 69-story condo tower project by 2029.

As I pass a striking Victorian house at 141 Isabella Street, I notice that the leafless ivy on its side has grown into the lovely shape of a tree.

I admire one last stylish Queen Anne Revival house (168 Isabella St.) dating from 1887, thinking that it is potentially the candidate for another restoration project of integration into a modern building.

Coffee break at Piedmont

Retracing my steps, I stop for my caffeine fix at Piedmont Coffee Bar (66 rue Isabella). Seduced by the green and pink retro feel, I order an excellent coffee (made with beans from De Mello roasters).

Many tables are occupied by customers with computers. The café’s menu is perfect for this kind of clientele, offering among other things exotic toasts made with Japanese Shokupan bread, a brioche bread with milk that they also sell in the shape of a perfect cube!

On the west side of the café, intricate laser-cut metal balconies already adorn some floors of a new luxury condominium tower under construction. Looking around, I wonder how much longer the more sober and less spectacular Mid-Century buildings will survive.

In the heart of rue Isabelle, I begin to ponder about the passage of time and its impact on a city... and people. Just like the architecture of urban environments, we evolve in constant mutation.

For a longer walk

I highly recommend adding 1-km to the walk at the intersection of Isabella and Sherbourne (in which case you'll want to stop at Piedmont Coffee Bar first).

Cross Shernourne Street, turn left northbound, and right on Howard Street. Then take the second street on your left. You're now on dead-end Glen Street, where you'll be surprised to find an entrance to Sherbourne subway station...

(UPDATE as of February 19, 2023) There used the entrance to a tunnel running under Bloor Street! One of my readers was nice enough to let me know it is currently closed for renovations. I went to check it out. See the following before and after pictures.

When it reopens, it will allow you to discover a hidden gem, the pedestrian bridge which passes over Rosedale Valley Road. It offers a gorgeous view over one of Toronto's most country-like streets. I hope the renovations won't change it too much!

Until then, I suggest you climb up the stairs to Bloor, and turn left, then left again into Huntley Street. You will see stairs leading you to Mount Pleasant and the gorgeous murals on both side under the Bloor viaduct.

This post is a complement to local author Nathalie Prézeau's walking guide: Toronto BEST Urban Strolls. You already own this book? Check Nathalie's WEEKLY WALKS calendar available on her site It's free, easily printable by season, and it includes page references which should help you enjoy urban walks year-round.

Nathalie's guides are available in Toronto’s major bookstores, on and or We also deliver or contact the author directly at to arrange for a pick up with a discount at 299 Booth Avenue, in Leslieville.


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