Our Favourite Historic and Iconic Toronto Buildings

Jan 20, 2021

Toronto is blessed with many buildings regarded as landmarks, either for their historical merit or because they have become icons of our cityscape – think the CN Tower, the legislative buildings at Queen’s Park, or Union Station. Here are our team members’ favourites:

Allan Gardens Conservatory
160 Gerrard St. E.

The conservatory was initially built in 1909 and featured a brick-clad base with sandstone detailing, and stone, wood, glass, and iron also being used as building material for the structure. Its 16-sided glass and steel dome was topped with a cupola. New greenhouses were added to the original, domed conservatory over the next century, and there are now six greenhouses, covering approximately 16,000 sq. ft., and providing a glorious respite for visitors, from the city’s noise, summer heat, and winter cold and snow.

Casa Loma
1 Austin Terrace

Casa Loma was built in 1914 as the home of Canadian financier Sir Henry Pellatt, whose travels to Europe and interest in the military spurred his vision of Casa Loma. With its soaring battlements and secret passageways, it remains one of the only true castles in North America. It is now owned by the City and is one of Toronto’s top tourist attractions and hospitality venues, welcoming over 650,000 visitors a year. Casa Loma also plays host to more than 250 private events annually, and is a highly desirable location for film, television and photo shoots.

Convocation Hall
31 King’s College Circle

This domed rotunda on the grounds of the University of Toronto was designed by renowned architects, Frank Darling and John A. Pearson, who were influenced by the Edwardian Baroque revival in architecture at the time. Competed in 1907, the hall’s interior has been compared to the great amphitheatre of the Sorbonne, in Paris. While the building’s purpose is to host the annual convocation ceremonies, it also serves as a venue for academic and social functions throughout the year.

Elgin and Winter Garden Theatres
189 Yonge St.

This double-decker pair of theatres were originally built as the flagship of Marcus Loew’s theatre chain in 1913, and are today the last surviving Edwardian stacked theatres in the world. Both theatres were built to show vaudeville acts and the silent movies of the time. The elegant, lower-level Elgin Theatre features gold and marble, with a domed ceiling, while the upper-level Winter Garden was built to look like a country garden under the stars, with murals of plants and trellises, and columns disguised as tree trunks. The Ontario Heritage Trust now owns and operates the theatres and runs tours (currently suspended due to Covid-19) that are well worth the time!

Evergreen Brick Works
550 Bayview Ave.

In 1904, after The Great Fire destroyed much of the downtown core, the then Don Valley Brick Works was where the bricks were produced that built many Toronto landmarks, including Massey Hall, the ROM and Casa Loma. Eventually, the brick works closed and fell into disrepair but, spearheaded by Evergreen, the crumbling heritage buildings have been transformed into a showcase for green design and urban innovation. Today Evergreen Brick Works comprises 16 heritage buildings and 16 hectares of wetlands, hiking trails and wildflower meadows. It is an incubator for small businesses and pilot projects, a venue for conferences and events, and the site of popular food, garden, and artisan markets.

Fort York National Historic Site
250 Fort York Blvd.

Preserved as a 43-acre archeological park, Fort York is where British soldiers, First Nations warriors, and Upper Canadian militiamen stood together against the United States and their mission to capture Toronto in the War of 1812. The bloody Battle of York that ensued was a dark and dramatic moment in the history of the city. It’s hard to imagine what happened at this spot so long ago when you drive by Fort York on the Gardiner Expressway, on your way home or to work. Today, visitors to Fort York can relive moments of the battle through an immersive multimedia experience and live demonstrations by volunteers in period costume.

Gooderham Building (also known as the Flatiron Building)
49 Wellington St. E.

This unique, wedge-shaped building, located on a triangular parcel of land where Wellington Street East diverges from Front Street East, is probably the most photographed building in the city. Constructed in 1891, to house the offices of the Gooderham & Worts Distillery (see below), the Flatiron was the most expensive office building of its day, coming in at a cost of $18,000! Today, the Flatiron Building still houses commercial offices, as well as a popular pub in the basement.

Gooderham & Worts Distillery (the Distillery District)
Trinity St.

This distillery, founded in 1832 and now protected by the Ontario Heritage Act, is described by National Geographic as a “top pick” for travellers to Toronto. Close to 30 of the original buildings, including the Stone Distillery, still exist and have been transformed – through an inspired blend of Victorian Industrial architecture and stunning, 21st century design and creativity – into an internationally-acclaimed village of one-of-a-kind shops, galleries, studios, restaurants, cafes, theatres, and more. The Distillery District really comes alive during its annual Christmas Market, a long standing tradition.

The Grange
317 Dundas St. W. (in the AGO)

This centre-hall, grand Georgian residence was built in 1817 for lawyer, D’Arcy Boulton Jr., and his family. It eventually became the first home of what is now the Art Gallery of Ontario, and has been exquisitely preserved and incorporated into the back of today’s modern AGO, where it now houses the members’ lounge, as well as exhibition spaces. The house retains its historic roots and architectural integrity, and visitors to the AGO are free to enjoy the beauty of The Grange and to explore its exhibits. Two centuries after it was built, The Grange continues to stand proud over Grange Park with its outdoor sculptures.

Hockey Hall of Fame
30 Yonge St.

The hall of fame occupies the former Bank of Montreal building, now part of Brookfield Place, in the city’s financial district. The historic bank building features two fine, monumental pedimented facades, and dominates its location at the corner of Front and Yonge streets. Designed by Frank Darling and S. George Curry, it was completed in 1886 and continued in business as the Bank of Montreal until 1982.

Lillian Massey Building
125 Queen’s Park

Lillian Massey, heiress to the Massey-Ferguson empire (also responsible for Massey Hall and Hart House), believed that a home should be run scientifically – doubtless a radical idea at the time and perhaps still is! She therefore funded the construction of this building to house the University of Toronto’s Department of Household Sciences. Designed by prolific Toronto architect, George Martel Miller, the grand, Neoclassical-style building was completed in 1912. It is currently owned by Victoria College, U of T.

Mattamy Athletic Centre
50 Carlton St.

Today, the building houses the athletic centre of Ryerson University, as well as a ground-floor Loblaws store. But most Torontonians remember this as a cathedral of hockey: Maple Leaf Gardens. This is where the Leafs won their 11 Stanley Cups (if you can remember back that far!), and where the first-ever NHL All-Star Game took place, in 1947. Constructed in 1931, the building’s simple aesthetic draws on the Art Deco and Art Moderne styles of streamlined form and decorative geometrics. It’s a superb example of a historic building being successfully repurposed for community use.

Montgomery’s Inn
4709 Dundas St. W.

The main section of this building, erected in 1832, is one of Ontario’s finest remaining examples of Loyalist Georgian architecture. Montgomery’s Inn sheltered travellers, provided space for public meetings, and brought people together over food, drink, and games. Today, it’s a lively museum, giving visitors the opportunity to see how a 19th-century Canadian inn was run from ballroom to bedrooms (with a kitchen and bar still in full working order) and to hear the stories of guests from days gone by. Visit for the history, the pub nights, ghost stories, live music, hearth cooking demonstrations, and the farmers markets!

R.C. Harris Water Treatment Plant
2701 Queen St. E.

Sited majestically above Lake Ontario in the city’s Beach neighbourhood, this is both a crucial piece of city infrastructure and an architecturally-acclaimed historic building, named after the long-time commissioner of Toronto’s public works R. C. Harris. The Art Deco landmark was designed in the 1920s and completed in 1941. The plant is not usually open to the public, but if it’s on the list for the next Doors Open Toronto, don’t miss the opportunity to tour this breathtaking complex, with its soaring, arched windows, marble floors, and bronze railings. The most palatial work of city infrastructure you may ever see.

Royal Conservatory of Music and Koerner Hall
273 Bloor St. W.

Two beautiful buildings spanning a century of architectural design, joined into a single venue for the teaching and enjoyment of music. McMaster Hall, fronting onto Bloor Street West, is a richly-ornamented building of eclectic late-Victorian design, a National Historic Site that houses the Royal Conservatory of Music. Visitors to Koerner Hall, the modern, glass-walled concert building behind the RCM, access that space via a soaring, glassed-in atrium that provides a breathtaking link between the old architecture and the new. The interior of the concert hall features an all-wood canopy, that provides extraordinary acoustics and a warm counterpart to the glass walls of the lobby space.

St. Lawrence Hall
157 King St. E.

Another National Historic Site, elegant St. Lawrence Hall was constructed in 1850, as a venue where Toronto’s elite could gather for social events, including debutante balls, recitals, and exhibitions. Restored to its original grandeur in 1967, St. Lawrence Hall, with its three major event spaces, continues to serve as one of the city’s most stunning venues for special occasions certain to make a lasting impression.

St. Lawrence Market
93 Front St. E.

All roads to good food lead to St. Lawrence Market, a city landmark since 1803. Here, some two hundred vendors sell everything from local mustard to fresh pasta, to lobster, to artisanal bread. But, more than a place to indulge the foodie in you, St. Lawrence Market is also a neighbourhood hub for the area’s condo dwellers, and on weekends draws people in from all around the city, to its vibrant atmosphere and colourful vendors.

St. Stephen-in-the-Fields
103 Bellevue Ave.

This Kensington-area church, built in 1857 (and actually in the fields at that time), is a superb example of mid-19th Century Gothic architecture. Its stained-glass windows are among the finest in the city. And it is not only a wonderful building, but also a force for good. Like many downtown churches, St. Stephen has embraced the mission of caring for the hungry and the poor of its community, and offers services in English, Spanish, and French for its Caribbean, Latino, and African congregations.

Scadding Cabin
CNE Grounds

Toronto’s oldest known surviving house was constructed in 1794, during the first years of British settlement here, for John Scadding, a friend and assistant to Lieutenant-Governor John Graves Simcoe. The cabin was built on the east bank of the Don River, on a 253-acre parcel of land stretching from Lake Ontario north to present-day Danforth Avenue. In an early act of heritage preservation, the cabin was dismantled and reassembled at its current location in 1879, for the inaugural Toronto Industrial Exhibition (now the Canadian National Exhibition). Scadding Cabin is open to visitors during the CNE, when they are welcomed by volunteers in period costume, who explain the cabin’s history, describe artifacts, and demonstrate spinning.

Todmorden Mills Heritage Site
67 Pottery Rd.

You may not notice it as you speed along the nearby Don Valley Parkway, but this site, nestled in the Don River valley, is an ode to the industrial past of our great city. Todmorden Mills was a small settlement that started out as a lumber mill in the 1790s. Today, the former manufacturing space is an open-concept and light-filled venue for book launches, art expositions, and other special events. The original kiln chimney stands tall and confident, as part of Toronto’s history of producing beer, flour, bricks and lumber. Add this as a destination on a weekend hike or bike ride.

Toronto City Hall
100 Queen St. W.

A favourite among Torontonians, as well as among visitors to the city, the “new” Toronto City Hall was a truly unique design when it opened in 1965. It was designed by Finnish architect, Viljo Revell, and landscape architect Richard Strong, winners of an international competition led by then Mayor Nathan Phillips (after whom the square in front is named) that yielded over 500 design submissions from 42 countries. The building is the symbol of Toronto, and its plaza is home to art and craft fairs, other special events, and to a popular skating rink in winter.

Wychwood Barns
601 Christie St.

Constructed in 1913, this was a TTC streetcar repair facility, before it was transformed into a community cultural hub in 2008. The site now comprises 26 artist live/work studios, 12 commercial/office spaces, a greenhouse, an art gallery, and a large event venue. Notably, this was the first redevelopment project in Canada to receive LEED Canada certification. It’s a wonderful place to take in art exhibitions, summer concerts, and to just relax in the park that surrounds the barns. And don’t miss their ever-popular Trivia Night Fundraiser….Toronto’s largest live trivia game!