Though Toronto has evolved into a concrete jungle, there are a number of historical gems around the city. Rich with history, these buildings give us a glimpse into what the 6ix once was. Whether it’s a midtown castle or the old stomping grounds of the Toronto Maple Leafs, these buildings serve as a reminder of the culture our city was built upon. Nestled between skyscrapers and condominiums, these pieces of architecture are must-sees for both locals and tourists. Keep reading for some of our favourite historical buildings in Toronto. Whether you are a seasoned local or a first time tourist, these stunning structures offer endless photo ops, as well as stories which are rich with culture. 

Casa Loma 

Once upon a time, a man named Sir Henry Pellatt decided to build a castle for him and his wife. Casa Loma, which is Spanish for “castle on the hill”, took three years to build starting in 1911 and cost over $3 million. It boasts 98 rooms, 30 bathrooms, and a library with enough room for 10,000 books. Pellatt had planned to include an indoor pool, three bowling alleys and indoor shooting range but they were never completed. The unique architecture was inspired by Pellatt’s fascination with the medieval castles he saw while on a trip to Europe. Today, Casa Loma serves Toronto as a popular tourist spot and event venue.

Photo: earjhzz from Instagram

Gooderham Building

You may be surprised to learn that Toronto’s flatiron building actually came before New York’s famous flatiron. This iconic structure is found at the corner of Wellington and Front streets in the heart of the city. The Gooderham Building, named after an affluent family in the community, was completed in 1892 after a year of construction. In 1975 it was officially named a historic site and in 2012 a realty group purchased the building. Today it’s rooms are rented out to brokers and tenants but the highlight of this building is the outside. It’s unique shape and Romanesque Revival and French Gothic architecture, make it the perfect backdrop to any photo.

Maple Leaf Gardens

Now transformed into Ryerson’s Athletic Centre and a Loblaws, Maple Leaf Gardens used to be home to Toronto’s beloved hockey team. In fact, the last time the Leaf’s won the Stanley Cup in 1967, they played at Maple Leaf Gardens. This historic arena was the site of sporting events, rallies, and concerts featuring iconic artists such as Elvis and The Beatles.  Though it’s now occupied by student athletes and groceries, Maple Leaf Gardens preserves its history through its exterior. Additionally, some of the seats from the original arena were preserved and are displayed as a maple leaf for past and present fans to admire.  

Photo: ohlofficial from Instagram

Osgoode Hall

Nestled in the heart of Toronto for almost two centuries, Osgoode Hall is a haven for lawmakers and law enthusiasts. Spanning over six acres, the historic building features heritage courtrooms from the 1800s. The Convocation Hall boasts ten stained glass windows depicting over 4000 years of law. Guided tours are offered by appointment from September to June and daily in July and August. If you’re more of a solo explorer, you can try the audio tours that are offered year-round.