Cobblestones to Skyscrapers: Exploring Old Toronto

Toronto’s rich history comes alive in Old Toronto, an area that refers to the oldest original part of Toronto. Now home to various districts, charming architecture, picturesque streets and hidden alleys, Old Toronto is a treasure trove of experiences waiting to be explored.

Toronto harbor skyline with CN Tower and skyscrapers
Toronto skyline. Photo Credit: DepositPhotos

Toronto is a cosmopolitan city that’s constantly evolving and growing, but as much as it changes, some parts of it have worked hard to maintain their original charm. Old Toronto, also known as the historic core, remains the heart of Toronto, no matter how big it gets. And it remains one of my favorite places to eat, drink and explore while in T.O.

Whether you’re a history buff, love exploring different cultures, are looking for an amazing dining experience or are just looking for an adventure, Old Toronto is a must-visit destination.

Toronto’s History

Settled by French explorers in the early 1700s, Toronto wasn’t founded until 1834. At that time, Old Toronto was the entirety of the city, and the boundaries weren’t expanded until the late 1800s and early 1900s. 

Initially, the area played an essential role in developing the city and the whole country. It was a major center of commerce and industry, with factories and warehouses dominating the landscape. There were also theaters, music halls and galleries to entertain workers and residents.

The area underwent significant changes in the mid-20th century when many historic buildings were destroyed to make way for new buildings and developments. However, like many other cities, there’s been a renewed focus on preserving and restoring historic buildings and landmarks in recent years.

Old Toronto Today

The boundaries of Old Toronto aren’t clearly defined, and they can vary depending on who you ask. However, it generally refers to the downtown area loosely defined as south of Bloor Street, east of Bathurst Street and west of the Don River. 

Don’t be fooled; this is still a vast area, home to many businesses, residents, buildings and more. Within this area, you’ll find several major districts, including

The Financial District

Royal Ontario Museum exterior.
ROM. Photo credit: DepositPhotos.

The Financial District is a bustling and dynamic neighborhood in downtown Toronto. The boundaries of this area are roughly defined as University Avenue to the west, Front Street to the south, Yonge Street to the east and Queen Street to the north. 

It is home to some of the most iconic buildings in the city, including the CN Tower, Scotia Plaza, and First Canadian Place. More than 200,000 people work in this district, which is always buzzing with activity.

You’ll also find the Royal Ontario Museum and the Art Gallery of Ontario here. If you look below the city streets, you’ll find The Path, a labyrinth of underground walkways lined with shops, restaurants, businesses and more.

Easily accessible by public transit, the area is walkable, friendly, safe and clean.

“The Financial District is my favorite place on earth and I fell in love with Toronto the minute we landed. The magnificent views, clean roads, lovely people, vibrant night life and more won us over. We stayed in the Financial District with a clear view of the CN Tower, and the great selection of restaurants and bars, coupled with excellent shopping, provided us with everything we needed.” 
— Zuzana Paar, Lowcarb-Nocarb

St. Lawrence District

St. Lawrence Market exterior.
St. Lawrence Market. Photo caption: All The Best Spots.

St. Lawrence is a historic neighborhood filled with charming streets, world-class restaurants, many homes and small parks, and if you’re a foodie, you’ll find the world-renowned St. Lawrence Market in this area.

The St. Lawrence Market is a historic building that’s been in operation for more than 200 years. Home to over 120 vendors, you can find everything here, including many quick lunch options or the ingredients to make everything from a humble dinner to a gourmet meal of steaks and salmon.

Fresh oyster display.
Fresh Oysters at St. Lawrence Market.

This is a pedestrian-friendly area, with many streets closed to cars. It’s perfect for leisurely meals at sidewalk cafes, cold cocktails or just people-watching. Or, check out the Young Centre for the Performing Arts and take in a show.

You’ll also find many different festivals in this district, including the annual St. Lawrence Market Summer Series and the famous Christmas Market.


Corktown is a charming historic neighborhood in the downtown core. Located south of Shuter Street, north of the Gardiner Expressway, east of Parliament Street and west of the Don River, which runs to the east, this is a lovely area with a long history.

Originally settled by Irish immigrants, you’ll find Victorian-era homes and modern condos side by side. Tree-lined meandering streets lead to parks and greenspaces, including Corktown Common, which features a playground, splash pad and stunning skyline views.

There are many studios and galleries in the area, too. It is an upcoming area in the foodie scene with trendy restaurants, Irish pubs serving cheese toasties and other traditional dishes and bars. 

Corktown is just a short walk from other districts, including the Distillery District and the St. Lawrence District, making it a great spot for anyone who wants to live in downtown Toronto.

Distillery District

Distillery District, Toronto.
Distillery District. Photo credit: DepositPhotos.

Complete with cobblestone streets, the Distillery District is a trendy area in the core. Revitalized in recent years and with a real sense of history, you’ll find Victorian-era architecture wherever you look. 

This area is a thriving arts and culture destination with many galleries and studios, including the famous Thomson Landry Gallery and the Corkin Gallery
Also a mecca for shoppers, you’ll find everything from trendy fashion boutiques and high-end decor shops to small stands offering handcrafted jewelry and other crafted goods. If all that shopping wears you out, stop by one of the many restaurants, breweries, pubs, cafes or bars to unwind.

“The Distillery District is a wonderful stop for families visiting Toronto as it’s completely closed to traffic! It’s just a short walk from downtown and is filled with places to shop, as well as some really yummy options to grab a bite. The buildings are beautiful, and there are also murals and sculptures easily accessible as you walk around.”
— Siobhan Borland, Mimosas and Motherhood

The final word

From the cobblestone streets of the Distillery District to the skyscrapers of the Financial District, Toronto is a city as diverse as it is huge. There’s something for everyone in this bustling city, so pack your bags and spend a few days or a week discovering all the best that lively Old Toronto offers.

This article originally appeared on Food Drink Life.

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