Be the Leading Lady in Your Life.

Travel

A Toronto Favourite: Kensington Market

a storefront in kensington

Lifestyle

Portugal

Discover life in Portugal.

TOp categories:

Travel

Unlock travel treasures to help you plan your next trip.

Literary

Find your next must-read from our specially-curated recommendations.

Hey there!

We're Isabel & Marilyn

We’re sisters with creative hearts and souls who dig deep to bring you valuable and meaningful information to help you shine as the leading lady of your life.

Explore how to live a healthy lifestyle, inside and out.

Get insider tips on what to pack for your trip to Lisbon

Year-Round Edition

(So you can be ready)

Are you on the list?

Be the first to know about recommendations, sneak peeks on life in Portugal, exclusive content, and much more!

I want the guide!

Kensington Market Toronto (not to be mistaken with the one in London, England), remains a favourite haunt for residents, despite, or perhaps because, of its constant transformation.

Oh, how it has changed over the years. The Kensington Market of this week will not be the same Kensington Market a year from now. It’s almost artistic in the way that it changes, and each of these changes tends to reflect back the wider picture of what is happening to the city itself. While this is true to some extent of most places, here it is especially so.

neon welcome sign of kensington mi amor
(South American influence: “Kensington Mi Amor.”)

Kensington Market’s Rich History

Walking through this colourful neighbourhood brings back old memories. There is an undeniable nostalgia for us whenever we go there as it is a place loaded with memories. What happened to all the stores long gone? And really, why did the bulk bean store and fresh fish stores have to go?

This place is filled with history. Members from Toronto’s Jewish community began the market in the early 1900s, with new immigrant groups also settling into the market. Growing up, it was filled with Jewish, Italian and Portuguese shops. Little remains of that history now, replaced with stores that reflect the arrival of newer immigrant groups. It’s as if the market is a live history book.

We thought we’d share with you what we liked most about Kensington Market Toronto from this visit.

Take a look.

Spend a Day in Kensington Market Toronto

welcome to kensington mural
(Welcome to Kensington Market Toronto)

The Kensington Market neighbourhood extends to include residential areas, and even the elementary school, Kensington Community School. It is downtown, near the University of Toronto, and right next to Chinatown.

According to The Canadian Encyclopedia,

a statue on college near Augusta
(Statue of Jesus begging called, “Whatsoever you do.” outside the Church of St. Stephen-in-the-Fields. Incidentally, in 2013 the statue was stolen for a brief period of time, and then return with a note of apology. There is a homeless encampment in the church’s front yard, but we did not take a photo out of respect for the people living there.)
row houses near park in kensington market
(When our dad first came to Canada in the 1960s, he rented a room in one of these row houses. That house was valued at $12,000 CAD.)

art vendors in kensington market
(In this trendy neighborhood, there is a combination of residential and business housing.)

A Nod to Lisbon

The market itself, specifically where the main stores are, has expanded from the times of our childhoods. Still, the Main Street remains the same: it’s Augusta Avenue (we think this is a nod to the popular Rua Augusta in Lisbon’s Chiado neighbourhood). It was at the market that our family would run into the newest arrivals from back in Portugal, and meet old friends, find Portuguese newspapers, get traditional food like cod fish, and clothes (practical and inexpensive). The Portuguese bookstore had outside speakers, turned on to an impossibly high volume with Portuguese news and often, men would gather around to meet up with friends to catch up on news. You’d probably do more socializing than shopping on a Saturday.

an alleyway with panted murals
(The whole area is a canvas.)

kensington market wall mural
(Bikes are a favourite mode of transportation. In warm weather, they take back the street from cars.)

heart painted on a sidewalk in downtown toronto
(For the joy of art.)

king of kensington al waxman statue
(The small Bellevue Square park has probably gone through a dozen main changes since Isabel, who is the eldest, played there. It was more child-friendly before, but it’s always been a place for everyone to enjoy. There is a more recent edition of a statue of Canadian actor, Al Waxman, who for many years starred on the Canadian show, “King of Kensington.” He was a beloved Canadian icon, who mentored students later in life. Isabel remembers him as a kind and devoted family man, who delighted in the craft of acting.)

wanda's pies
(Wanda’s Pie in the Sky is a neighborhood favourite for homestyle pies, cakes and other goodies.)

fruit market in kensingon market
(Once upon a time, this sight was common here, but not it’s the only store with outside displays of fruit and vegetables.)

bikes against a white picket fence
(Bicycles everywhere throughout the neighbourhood.)

This special neighbourhood is also not a very big. It’s confined to a few streets, and it can get crowded in warm weather. The people watching is fun too since there’s an assortment of people.

Most Torontonians engage in a type of friendly distance, so you probably won’t be engaging in small talk with the people you meet as can happen in some other places. Torontonians are generally nice people–we have grown up here and Marilyn was born here, so we can attest to that, and we like to think we’re nice people ourselves. But there is a reserved quality to how most Torontonians interact. This may take some getting used to if you are accustomed to more friendliness, but it’s how Toronto is and has always been for us. Ask for directions and you will see the friendly side of Torontonians–we want you to enjoy our city because there is so much to like here.

Yellow building cheese store in Kensington Market Toronto
(The various buildings’ colours are fun.)

Despite the hype about Kensington Market, you must know that it is a very chill, low-key, bohemian place. There’s something sombre about it too, especially in the winter months. This happens more so as evening approaches and the stores begin to close. It tends to have a very unique vibe to other Toronto landmarks. It’s really a place to walk through, grab something to eat (there is plenty of variety), and choose something unique from one of the unique stores.

While there are a few vintage clothing stores, Courage My Love, is our favourite. It has some fun finds in good condition.

Snapshots of Courage My Love

More Streets and Shops to See

Exterior of Tom's Place in Kensington Market
(Tom’s Place is a clothing store that is a market staple.)

exterior of house of spice
(It’s always a fun place to explore.)

painted wall mural in kensington market
(A mural with “Sete Cidades” painted on it, which is a reference to a place in Ponta Delgado, São Miguel, Azores.)

Signs of Augusta and Kensington Market
(Street Signs at the College Street Entrance.)

When you’re in the market, you feel in a way, as if you’ve stepped away from the city. Although it can be described as bustling in the summer months, it has a different energy than anywhere else in Toronto.

two coffees
(We couldn’t leave Kensington Market without stopping for a coffee.)

As the market evolves, people are creating their own memories and traditions here. It’s that kind of place.

Have you been to Kensington Market? Let us know what you think in the comments below.

-Isabel & Marilyn

Save this post!

+ show Comments

Add a comment:

- Hide Comments

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Sara says:

    What a great city!

(So you can be prepared)

Get insider tips on what to pack for Lisbon

Steal this!

What to pack for lisbon


Year-Round Edition

*When you sign up to receive this freebie, you will be added to our newsletter. You can unsubscribe at any time.

Spring, summer, fall, and winter included!

We share of love of Lisbon, Chihuahuas, sushi, coffee, binge-worthy tv, movies, being out in nature, the ocean, and our amazing mom.

And of course, we love literature and appreciate a kick-ass lipstick.






We're Isabel and Marilyn, the two sisters behind Letters and Lipstick.









learn more

Letters and Lipstick is for the woman who wants to be the leading lady in her own life.

The one who reads, the one who discovers, and the one who celebrates all good things big and small.

Welcome!
We're glad you're here.

Get Your Journal Prompts and Start to Write.

Go from "What do I even write about?" to "Shhh, I'm writing." 

Discover 25 journal prompts that are easy but effective to get you started.

Ignite your spark and start a solid writing practice.

*When you sign up to receive this freebie, you will be automatically added to our newsletter. You can unsubscribe at any time.

free download