Explore the rich architectural history on Yonge Street: how its buildings and public spaces have encouraged Torontonians to gather, celebrate, and do business for over two hundred years.
Yonge Street stands collectively in our minds as Toronto’s Main Street. The architectural development of Yonge Street over the centuries has shaped how people come together and experience life in Toronto.
This major urban artery began in the 1700s as a simple dirt trail, which ran north through rural prairies and forests. The road was expanded in the 1790s by John Graves Simcoe, Upper Canada’s first lieutenant-governor, who named it after Sir George Yonge (1731-1812), the British Secretary of War.
Yonge Street has often been called the world’s longest street, extending from the north shores of Lake Ontario north to Pine Fort Landing (Holland Landing), over 50 kilometres away. Today, it stands as a bustling street filled with crowds of shoppers, restaurants, cafes, theatres, and shops. It’s where Toronto’s east side meets its west side: where the city comes to shop, to meet, and to celebrate.
Using the table of contents (left) and the map below, explore the past and present architecture of Toronto’s Main Street.
This digital tour was made possible by the generous support of our Tours Program Presenting Sponsor, TD Bank and The Ready Commitment.
This tour was developed by Emerging Historian Stephen Ficalora, with the support of the Downtown Yonge BIA and the Ontario Association of Architects.
The evolving use of Toronto Fire Hall 3 represents the ever-changing nature of Yonge Street. Built in 1871, the Hall was designed by James Grand and William Irving in the Second Empire style. A popular feature of fire halls at the time, the building’s clock tower combined Italianate details and a mansard roof commonly seen in the Second Empire style. The building ceased operation as a fire station in 1929 and was renovated to house several businesses over the next 30 years, including a bicycle shop and car dealers. In 1950, Charles Hemstead opened the St. Charles Tavern in the old fire hall building, which still featured its now-famous clock tower.
During the 1960s, the area surrounding Yonge and Wellesley Street was a popular destination for Toronto’s gay community: home to bars and taverns like the St. Charles Tavern, the Parkside Tavern (530 Yonge Street), and the Red Lion Room at the Westbury Hotel (now the Courtyard Marriott at 475 Yonge Street). Over the next decades, St. Charles’ clock tower as well as the Tavern’s advertising catchphrase, “Meet me under the clock”, became early visible symbols for the city’s queer community.
The St. Charles Tavern closed in 1987 and the property operated as several more clubs and businesses until 2018, when it was sold to redevelopment for a mixed-use condo. The famous clock tower was listed in the Toronto Inventory of Heritage Properties in 1974 and was designated as part of Historic Yonge Street in 2016 under the Ontario Heritage Act.
Dennis Findlay, President of the Canadian Lesbian and Gay Archives, 2018
Social clubs were popular in Toronto in the 19th and 20th centuries, where members could socialize, make business contacts, and hold meetings. Many social clubs of this time were international organizations. Newcomers to Toronto often could find a foothold in Canadian society through social clubs, joining the Toronto chapter of an organization they had belonged to back home.
One social club in 19th century Toronto was the Independent Order of the Oddfellows. Its lodge at 450 Yonge Street was completed in 1892 and is the order’s oldest surviving lodge in Toronto. Designed by Norman B. Dick and Frank W. Wickson, the four-storey building features both Gothic Revival and Château elements. The Hall was among the first commercial buildings on College Street west of Yonge Street, which, until 1889, had been a private road leading to the gates of University of Toronto.
The Hall was built with the Oddfellows lodge occupying the upper floors and independent offices and stores on the ground floor, which were rented out to generate income. One of the original ground-floor tenants, a branch of the Canadian Bank of Commerce (today CIBC) occupied the site for over one hundred years.
Oddfellows Hall is also home to one of the few surviving electric Otis-Fensom elevators, which can also be found in the Gladstone Hotel and the Elgin and Winter Garden Theatre.
A major contributor to the commercial growth of Yonge Street was the development of Eaton’s College Park store in the early twentieth century. Already a prominent department store in Toronto by 1900, the T. Eaton Company Ltd. looked to expand their retail empire north to College Street.
Sir John Eaton (son of company founder, Timothy Eaton) proposed the original vision for a flagship store at Yonge and College, hiring Canadian architects Ross and Macdonald to plan a 32-storey skyscraper. Had the original plan materialized, it would have been the largest office and retail complex in North America. However, the Great Depression made construction difficult and the project was reduced to a modest seven storeys.
The final building complex displays elements of the Stripped Classical Art Deco style, used in many government and financial buildings during the 1920s and 1930s. Stripped Classical incorporates flattened facades and columns, alongside a focus on symmetry and simple designs. French architect René Cera designed the interior of the building, featuring grey marble paving from the south of France and colossal pillars set 40 feet apart.
When the store opened on October 30, 1930, it was one of the largest department stores in Toronto, selling everything from cosmetics and clothing to imported European furniture and art. The store featured a Sculpture Court and Fine Arts Gallery, which included a reproduction of Rodin’s Thinker as well as a copy of Rembrandt’s Portrait of a Seated Woman with a Handkerchief (now on display at the Art Gallery of Ontario).
The Globe, October 31, 1930, p. 13
Eaton’s College Street offered more than department store shopping: a world-renowned concert hall and restaurant could be found perched on the seventh floor of the building. Designed by Jacques Carlu in an Art Moderne style, the Eaton Auditorium became an important centre for the arts in Toronto. Featuring sleek geometrical designs and muted colour schemes, the Auditorium opened in 1931. Over the years, it hosted international performers, including Glenn Gould’s professional debut in 1945.
In the restaurant, the Round Room, or the adjoining Clipper Room, Lady Eaton could be found dining in a private alcove or enjoying a fashion show. Inspiration for the restaurant’s Art Moderne ocean liner design came from Lady Eaton’s frequent transatlantic cruises during the 1920s. Jacques Carlu used the geometrical designs and colour schemes of 1920s ocean liners to evoke a similar transatlantic atmosphere to the seventh floor. Both the Eaton Auditorium and the restaurants were closed in the 1970s following the sale of the Eaton’s College Street building. The seventh floor was sealed off and suffered from decades of neglect.
Beginning in 2000, WZMH Architects and ERA Architects, together with entrepreneurs Jeffry Roick and Mark Robert, undertook a restoration project of the seventh floor for $8.5 million. The space reopened as the Carlu event venue, re-named in honour of its original designer. It won the Architectural Excellence Award from the Ontario Association of Architects in 2004 and remains a prominent event space in Toronto today.
Eleanor Koldofsky
The Toronto Star, April 27, 2003, p. B6
Today, Yonge Street is a natural destination for shopping, dining, and entertainment in downtown Toronto. But, amid the restaurants, dance halls, and department stores, can also be found a long history of public recreational and educational spaces in the city. In the late 19th and early 20th centuries, the first Toronto chapters of the Young Men’s Christian Association (YMCA) and the Young Women’s Christian Association (YWCA) erected purpose-built buildings on Yonge Street to offer classes, social events, and education to the surrounding community.
Beginning in the late 1880s, both the YMCA and YWCA called Yonge and McGill Streets home. The YWCA Building at 21 McGill Street was completed in 1892 and was formerly known as William Gooderham Hall after Toronto’s distillery magnate. Specially built for holding lectures and classes for women, the building also featured an indoor pool, one of the first public swimming facilities for women in the city. Several women’s clubs operated out the Hall throughout the 20th century, including Toronto’s first private women’s club, 21 McGill Club. Gutted by fire in 1980, it was extensively renovated in the 1980s. Today, it remains a space for education and gathering, home to Covenant House, an organization serving at-risk youth.
For much of its history, Toronto lacked one thing many cities have in abundance: public squares. Over the years, many plans were introduced for open public squares around Yonge Street, but none were ever realized. In the 1990s, two Toronto businessmen, Aaron Barberian and Bob Sniderman, devised a plan for a public space on Yonge Street. Other businesses in the area joined in the movement, and, in March 1995, formed the Yonge Street Business and Residents Association (YSBRA), the forerunner of today’s Downtown Yonge Business Improvement Area (DYBIA).
The YSBRA, with the help of City Councillor Kyle Rae, hired urban planner Ron Soskolne to put together a proposal to revitalize the Yonge and Dundas Street area. Toronto architects James Brown and Kim Storey were selected to make that proposal a reality: their simple, yet functional design envisioned a paved triangular space that included outdoor seating, a raised stage, along with a “Media Tower” featuring large neon signs and billboards, reminiscent of New York City’s Times Square.
Yonge-Dundas Square opened in 2003. It stands today as the heart of Yonge Street and a focal point for the downtown Toronto community. From the centre of the square, one can see the former Sam the Record Man neon store sign atop 277 Victoria Street. To the east are the restored Hermant Buildings, once the tallest buildings in Toronto during the 1910s-1920s. South, along Yonge Street is the site of the former music venue, the Friar’s Tavern. Today, the building is home to a Shoppers Drug Mart: upstairs, the space hosts the Friar’s Music Museum, a free museum dedicated to the history of music on Yonge Street.
John Barber
The Globe and Mail, May 31, 2003
Like the neighbourhood around it, the Church of the Holy Trinity in Trinity Square has changed significantly over time. The church was built in 1847, designed by Henry Bowyer Land, who also designed Little Trinity Church on King Street East. The church was built in a cruciform-shape in the Gothic Revival style, which recalls its medieval inspiration with corner buttresses and two turrets. These features give the church an appearance of being bigger than it really is (it’s only about five stories tall). Trinity Square also includes the church rectory, built in 1861, and the Scadding House, built in 1857.
Early plans for the construction of the nearby Eaton Centre in the 1970s suggested that the century-old church either be demolished or moved from its original location. The Church community refused to sell the building and surrounding area, now known as Trinity Square. Trinity Church remained where it was, although both the Church rectory and parish house (the two eastern buildings) were eventually moved to accommodate the new shopping centre. The Trinity Church community also negotiated with Eaton Centre developers to guarantee a certain amount of sunlight reach Trinity Square each day. The agreement was among the first of its kind in Toronto and led to current municipal guidelines requiring new buildings to provide access to sunlight to nearby properties and public spaces.
Since its founding, the Church of the Holy Trinity has been a place of welcoming and acceptance. In the 1930s, the Church opened its doors to those who experienced homelessness and unemployment due to the Great Depression. During the 1960s, the Church welcomed Vietnam War resisters from the United States, allowing them to use the basement as a hostel. In the 1970s and 1980s, it supported the gay community by hosting the Community Homophile Association dances in the church.
Today, the church’s location in the heart of downtown allows it to continue to provide outreach to the community: offering daily meals and hygienic supplies as well as an active outreach program for Toronto’s LGBTQ2S+ community. The space has also become an important venue for artistic events, hosting concerts, theatre performances, and lectures.
No other venue in Toronto is as synonymous with music and performance as Massey Hall. The building was commissioned by Hart Massey, a farming machinery magnate and one of Toronto’s richest men, in memory of his son Charles Albert, who died of typhoid in 1884. Prior to Massey Hall, Toronto lacked a large, public venue for music. Inspired by the Cleveland Music Hall (built in 1885), Massey hired Canadian architect Sidney Badgley to design a similar space for Toronto.
Massey’s eldest daughter, Lillian, was heavily involved with the Massey Music Hall project. She suggested the neoclassical late-Palladian style building, chose the Art Nouveau lettering on the facade, and approved the frieze of classical figures representing music, which once decorated the exterior pediment.
Badgley designed the building’s interior in a Moorish Revival style inspired by Eastern and Spanish architecture, with seating for 3,500. Details of the ornate wood arches and hanging wave-like decorations were painted in bright golds, reds, blues, and greens. Art Deco stained glass and an enormous 400-light gas and electric brass chandelier illuminated the Hall. Massey Music Hall opened on June 14, 1894 to a packed audience of Toronto’s and Canada’s most notable, including the then-Governor-General of Canada, Lord Aberdeen.
In 2018, Massey Hall closed to begin a $180 million restoration and expansion. The building’s original stained glass was uncovered for the first time in half a century and restored. The Hall’s famous fire escapes, not part of the Badgley’s original design but added in 1911, were removed. In 2020, the Massey Hall Revitalization project teamed with Allied Properties to integrate the historic Hall into the new Allied Music Centre, which offers two new stages and a seven-storey tower featuring studio space and artist labs. Reopened in 2021, Massey Hall is once again the centre of Toronto’s music scene; a place to meet, to experience the world’s greatest artists, and to celebrate life.
Built as the Canadian Bank of Commerce’s Queen-Yonge branch and opened in 1905, 197 Yonge Street recently has found new life as part of the mixed-use Massey Tower. Designed in the Classical style as interpreted by Beaux-Arts principles, the Canadian Bank of Commerce building was the work of Toronto architects Darling & Pearson and is considered one of their best works. A stalwart of Yonge Street frontage for over fifty years, the bank branch closed its doors in 1987, after which the building sat vacant for over twenty years.
In 2012, MOD Developments purchased 197 Yonge Street and the site of the former celebrated jazz venue, the Colonial Tavern next door. The Tavern, which opened in 1947 and saw the likes of Benny Goodman, Miles Davis, and Sarah Vaughan grace its stage, was demolished in 1987, leaving a vacant lot north of the former bank building.
MOD revitalized both the building and next-door lot by developing a multi-use tower in collaboration with ERA and Harry Pontarini Architects. A portion of the redeveloped site fronting Victoria Street was donated to Massey Hall as part of the new Allied Music Centre. Completed in 2019, the project was named “The Massey Tower” in honour of the Massey family’s vital role in the history of Toronto’s cultural life.
“The Music Legacy of Yonge Street: The Colonial” produced by the Downtown Yonge Business Improvement Area
From its Yonge Street entrance, no one would suspect that the Elgin and Winter Garden Theatre was, and remains, one of Toronto’s most spectacular architectural wonders. Built between 1913 and 1914, the Elgin — originally Loew’s Yonge Street Theatre — and Winter Garden Theatre was the first and only Edwardian double-decker or stacked theatre in Canada: a single building with two theatres on top of each other. Today, it is the last operating double-decker theatre in the world.
The theatre complex was the flagship location for Marcus Loew’s vaudeville and movie houses in Canada. Designed by Thomas W. Lamb, who also designed the nearby Ed Mirvish Theatre, the two theatres provided a distinct yet decadent atmosphere for the paying public. Loew’s Yonge Street offered a baroque fantasy, bedecked with cherubs and gold leaf. Upstairs, the Winter Garden featured hand-painted walls depicting a lush garden. From its ceiling hung real beech boughs and soft lantern lighting.
Through its vaudeville and movie offerings, Loew’s theatres sought to bring entertainment to the masses. Toronto’s traditional theatres at the time cost up to $2.00 a ticket (approx. $50 today), making it too expensive for many Torontonians to attend. But the affordable prices of both theatres made live entertainment and the new technology of motion pictures accessible to the wider Toronto community.
Both theatres suffered in the 1920s as vaudeville lost popularity with the paying public. The Winter Garden closed in 1928, while Loew’s Yonge Street continued to operate as a movie house into the 1970s, when it was renamed the Elgin. In 1981, the Ontario Heritage Trust purchased the building and restored the original grandeur of both theatres, including the gold leaf of the Elgin and hand-painted watercolours of the Winter Garden. In December 1989, the theatre complex reopened to live performances.
Today, the Elgin and Winter Garden is more than just a theatre. It has become one of the main centres of Toronto’s art and musical culture, hosting annual holiday pantomimes, film festivals, award shows, concerts, and more.
“Riches to Rags to Riches” produced by the Ontario Heritage Trust
Robert Crew
The Toronto Star, December 20, 1989
Today’s Eaton Centre takes its name from one of Canada’s most famous department stores, the T. Eaton Company Ltd. Timothy Eaton opened his first dry goods store in Toronto in 1869 at 178 Yonge Street. By 1883, the store’s success and popularity allowed Eaton to buy new buildings at 190-196 Yonge, roughly where the Eaton Centre stands today. There he built a single store, featuring large windows to display his goods.
The Yonge Street location became known as Eaton’s Main Store. For the next fifty years, Eaton’s would remain the heart of Yonge Street, although it also expanded throughout Canada. By 1930, Eaton’s employed over 25,000 people nationwide and controlled almost 60% of department store sales in the country.
In 1958, when plans were proposed for Toronto’s New City Hall complex, city planners approached Eaton’s about the possibility of redeveloping its land between Yonge and Bay Streets into a major retail centre to match the new civic buildings. The initial plan, designed by architects Mathers and Haldenby, would see Eaton’s Main Store, along with most of its adjoining warehouses, redeveloped into a massive retail and office complex. It took over ten years to finalize the scope of the redevelopment, but the proposed complex, named The Eaton Centre, received final approval in November 1973.
The Eaton Centre’s design was the brainchild of Eberhard Zeidler, who also designed Ontario Place. Taking inspiration from Italy’s oldest shopping complex, Milan’s Galleria Vittorio Emanuele II, Zeidler envisioned the Eaton Centre as an encased street with three levels of shops overlooked by offices. The “atrium” design of the centre was complemented with a simple modern design emphasizing concrete, steel, and glass.
The first phase of the Eaton Centre opened on February 10, 1977, with the second shortly thereafter in 1979. Thousands of Torontonians crowded the streets in and around Yonge Street, hoping to get in. The Eaton Centre underwent a significant expansion in the late 1990s, when it was extended further east to Yonge Street to create additional retail space. In 2019, the Eaton Centre welcomed over 52 million visitors.
