178 Victoria St

Massey Hall

In 1894, the Massey Music Hall opened its doors and 3,500 seats for its inaugural concert. A present to the city of Toronto by Canadian businessman, Hart Massey, the venue was built as a tribute to his late son Charles Albert Massey to aid in the development of the arts. Home to the Toronto Mendelssohn Choir and Toronto Symphony Orchestra, Massey Music Hall was used for a variety of functions including concerts, weddings, ballets, theatre, political and religious rallies among many other cultural and entertainment events.  Renovated in 1933, Massey Hall received a new look replacing the wooden stairs with stone and an updated Art Deco-style look. And in 1973, the City of Toronto names Massey Hall its first ever historical site. In 2013, both the Federal and Provincial governments announced they would each be allocating $8 million in funds to the revitalization of this historic cultural and entertainment venue.  Over the years the stage has been graced with a long roster of local and international talent including Paderewski, Emma Albani, Caruso, Tetrazzini, Luciano Pavarotti, Gordon Lightfoot, the Dalai Lama, Neil Young and Justin Bieber and is truly the foundation of the arts and culture scene in Toronto.



49 Wellington Street East
Flatiron Building (1)
Photo cred: Travel Past 50

Costing a mere $18,000, the Gooderham Building was designed and built by architect David Roberts, Jr in 1892 for George Gooderham, Sr. Sandwiched between Wellington and Front streets, the building, also referred to as the Flatiron, was the office of Gooderham & Worts Ltd, which at one time was Canada’s largest spirit distilleries, until 1952. The building remained property of the Gooderhams until the estate was sold in 1957. Under the Ontario Heritage Act of 1975 and resorted throughout the years by several owners, this iconic building was declared a historic site. Currently owned by The Commercial Realty Group, the Flatiron houses office space that is among the most expensive in the city.  On the west façade of the building a four storey mural, by artist Derek Besant, depicts a mirror image of the Perkins building which once stood just to the west.



92-95 Front St E

Named by National Geographic as the world’s best Food Market, this Toronto icon has a robust history over 200 years in the making. In 1803, Lieutenant General Peter Hunter declared that the land between what is now King Street (north), Jarvis Street (east), Front Street (south) and Church Street (west) would be the ‘Market Block’. A wooden structure was built for the market and in 1831 the first brick structure was built which would house local civic offices and was considered the business core. In 1845, the south market, designed by Henry Bowyer Lane, was built at a cost of $52,000 and became Toronto’s first permanent city hall in addition to being a jail house. Toronto’s Great Fire, in 1849, destroyed much of the Market Block including the brick building north of Front Street. In its place the St. Lawrence Hall was rebuilt in 1850 and still stands on the southeast corner of King Street and Jarvis Street to this day.  When the South Market was vacated by the city officials, it was renovated in 1899 to become a market place which reopened in 1902 and quickly became the hub of the city for many, many years to come. Threatened to be torn down by a Toronto City Planning proposal, the St. Lawrence Market was saved by a group of citizens who appealed this decision and won. It was renovated and restored between 1974 and 1978, and the once Council Chambers was turned into the Market Gallery which to this day showcases city artifacts. The present day St. Lawrence Market is hub for Toronto residents as well as tourists, housing 120 vendors selling culinary treats from fish and meats to fresh fruits and vegetables and baked goods. It is flocked to by foodies from near and far, and is a great reminder of Toronto’s rich history.



30 Yonge Street

Hockey Hall Og Fame2

Photo Cred: Toronto Spacefinder

Designed by Toronto firm, Darling and Curry, this stunning building located on Front Street and Yonge began construction 1885 and was head office to the Bank of Montreal of for over 60 years. Undoubtedly the pièce de résistance in this glorious building is the Esso Great Hall, a 70 by 70 foot-wide room with a stained glass dome measuring 45 feet high. The intricate detail of the ceiling and meticulous stained glass boasts imagery from dragons to eagles and gold to fruit and still to this day is the largest dome of its kind in Toronto.  This magnificent display of history and craftsmanship is now home to the Hockey Hall of Fame and the most cherished possession of the NHL, the Stanley Cup. It is fitting that such an iconic symbol of the 21st century resides in one of Toronto’s architectural statements of the 19th century.



Distillery District

Distillery District

Photo Cred: Artfest Ontario

Built in 1859 (completed in 1862) and originally built as an alcohol manufacturing facility, Gooderham & Worts Distillery was once the largest alcohol manufacturers in Canada. Brothers in law, William Gooderham and James Worts began the business in England as a grain mill in 1831 and moved to Toronto the following year. After the suicide of Worts in 1834, Gooderham became the sole decision maker of the business and by 1837 had decided to expand the business from a grain mill to alcohol distillery. Quickly the distillery became the main focus of the business and had grown enough that new manufacturing facilities were warranted. What is now known as the Distillery District, a popular city destination for residents and tourists alike, the Gooderham & Worts Distillery, despite being sold by Gooderham, operated for more than 120 years manufacturing different Canadian spirits, including a national classic, Canadian Club. After continual decline in production the facilities were closed in 1990. Now one of the most vibrant neighbourhoods in the city, the Distillery District is home to Toronto’s hottest restaurants and cafes, art galleries, boutique office spaces and condos.



1 Austin Terrace

Casa Loma

In 1911, business tycoon and chairman 21 companies., Sir Henry Pellatt, set out to build a near 65,000 square foot, 98-room castle fit for a king. Casa Loma, Spanish for house on the hill, was completed in 1914 at a cost of $3.5 million. Pellatt was only able to enjoy the fruits of his labour for a mere 9 years before he was consumed by debt and troubling finances and forced to move his family out of his dream home to a farm north of Toronto. This grandiose residence situated on the top of Davenport Hill, could rival any Bridal Path home today. A 10,000 book library, 100 seat dining room, 30 bathrooms, indoor swimming pool and indoor shooting range were among the luxurious amenities planned for the home, although not all were completed. Following Pellatt’s financial issues and before the castle was seized for overdue back taxes, for a short period was even a hotel and nightclub. Today, managed by Liberty Entertainment Group, Casa Loma is a premier event space like no other in the city, playing host to extravagant weddings and decadent events.

With so many stunning historical buildings in Toronto it was so hard to choose just six favourites. Let me know what your favourites are and I may have to do a runner up Top Six Historic Buildings.



  1. Great post! I love heritage buildings and you’ve covered a lot of my favourite buildings here. It’s sad how so many of our heritage buildings were destroyed in the 70s to make space for parking lots.

    Liked by 1 person

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