
The left side of the present-day photo shows McDonald’s, originally the Sunnyside Bus Terminal, built in the mid-1930s. Just behind it is Hotel Shelter (with the Howard Johnson Inn sign), built as the Edgewater Hotel in 1939.
On the right side of the current photo, notice the building home to Burrito Boys. It was constructed in 1910 for the Imperial Bank and also appears in the archive photo. The bank building was designed by architect Frank Darling and, since 2020, has been listed on the city’s heritage register as part of the Parkdale Main Street Heritage Conservation District (City of Toronto Archives, Fonds 1231, Item 1214)

Jean Ford Tolmie was crowned the winner after competing against over 65 hopefuls in the contest’s inaugural year. The archive photo shows her along with the four runners-up. The 1926 pageant was held at Sunnyside Bathing Pavilion in front of a crowd of 30,000, where Jean was crowned with flowers. The pageant was later moved to Exhibition Stadium & Grandstand in 1936.
If you look at the mural closely, you’ll notice the architecture of the Sunnyside Bathing Pavilion in the background, including the columns and decorative fence (City of Toronto Archives, Fonds 1244, Item 1028M)

The archive photo shows the entrances to the public underground lavatory along Broadview Ave, to the right of the Toronto-Dominion Bank. These public washrooms opened in 1910 and closed in the early 1980s (City of Toronto Archives, Fonds 2032, Series 841, File 25, Item 20)

Originally constructed in 1914/15, this building has a diverse history. It began as the location of the Davis Dance Academy on the main floor, while the second floor functioned as a residential apartment. Over time, the building transformed and housed a bowling alley and various commercial tenants.
In 1964, the property was acquired by Ann Dunn, who undertook renovations and established The Matador, a vibrant live country music club. The venue became a hotspot for legendary artists such as Joni Mitchell, Leonard Cohen, Gordon Lightfoot, and k.d. lang. After decades of performances, The Matador ceased operations in 2007. There are plans for a mixed-use development at this location (Toronto Public Library Lochist-BL-074)



The ghost sign was restored in 2020 and says “Gelber Bros. Limited Wholesale Woolens and Dress Goods.” Today, the building is home to commercial and office space


Built between 1928 and 1930, the architectural firms of Ross & Macdonald and Sproatt & Rolph designed the Art Deco landmark. The building was supposed to be much taller; however, due to the Great Depression, it was scaled back to seven floors.
The spacious store was Eaton’s headquarters for home furnishings. Upon opening, the store featured a series of period rooms, a fine art gallery and a library. On the basement level, there was a log cabin on display that could be built for customers “Summer haunts” by Eaton’s.
When the CF Toronto Eaton Centre opened in 1977, the College Street store closed. Since 1979, the heritage-designated building has been known as College Park (Archives of Ontario, T. Eaton Co. fonds, F 229-308-0-517.7)

In the photos, you can see the Canadian General Electric Company Building in the right foreground. It was built back in 1908 and served as the company’s headquarters. Canadian General Electric constructed the adjacent structure in 1917, followed by an extension in 1919. Just before the Royal Alexandra Theatre is the Nicholls Building, constructed in 1910.
The Royal Alex, an exquisite example of the Beaux-Arts architectural style, was built in 1907. Visionary Ed Mirvish saved the theatre from demolition in the early 1960s. His complete restoration of this building started rejuvenating what we know today as the Entertainment District.
All of these buildings still stand today and hold heritage designation from the city (City of Toronto Archives, Fonds 1230, Item 3562)

The building directly at the corner, at 39 Colborne St, was built in 1854. The archive photo shows when it was home to El Toro Steak House. Today, it’s P.J. O’Brien Irish Pub & Restaurant.
The row of four-storey commercial/warehouse buildings at 41 to 55 Colborne St date back to circa 1890. Today, they house various businesses and restaurants. The city has given all of these structures heritage designation (City of Toronto Archives, Fonds 1526, File 8, Item 116)




The church school building was replaced in 1909 with St James Parish House, which is today part of the St James Cathedral Centre.
The Mechanics’ Institute was a movement established in Britain to educate adults mainly in technical subjects. In 1830, the association came to the Town of York (Toronto). In 1854/55, with designs by architects Cumberland & Storm, the Institute constructed the building in the archive photo. However, due to a lack of funds, they had to rent it to the government for a few years before finally moving into the building in 1861. Lectures and classes were held there, plus there was an extensive reference library and a music hall. In 1882, the Free Libraries Act was passed, and the assets of the Mechanics’ Institute were given to the local government. Its vast collection of books started the Toronto Public Library, which opened in the building in 1884. The grand structure was torn down in 1950, and today, the site is home to a patio and mixed-use building (Toronto Public Library R-5981)

In the archive photo, notice the building with the tower on the far left. It was the Duke Street Public School. Adelaide St E between Jarvis St and Parliament St was once known as Duke St.
By the late 1940s, the Surgical Supplies (Can) Limited was in the long horizontal building at the corner with the curved façade. It later housed the Imperial Surgical Company and the Imperial Optical Company. In the late 1990s, the building was converted into the Imperial Lofts, which is shown in the present-day photo (Toronto Public Library B4-88C)


In the archive photo, notice the block on the left, which is now home to the CF Toronto Eaton Centre. The curved building at the corner was constructed in 1895 for the Philip Jamieson & Company department store. Over the past century, the building has housed various commercial tenants. There were plans to salvage and restore much of the original structure; however, due to decades of wear and tear, a replica of the building was built at the site. This replica is hidden behind scaffolding, as shown in the present-day photo.
The building in the foreground on the right was constructed between 1909 and 1910 as a branch office for the Bank of Montreal. It was designed by architects Darling & Pearson in the Edwardian Baroque style. The bank’s historic façade has been incorporated into the modern, 19-storey office tower known as 2 Queen St E (City of Toronto Archives, William James Family fonds, Fonds 1244, Item 495)

In the archive photo, notice FW Woolworth and the block on the left, which is today home to the CF Toronto Eaton Centre. The vintage photo also shows the historic Loew’s Theatre in the distance on the right. Nowadays, it’s known as the Elgin and Winter Garden Theatre Centre (City of Toronto Archives, Series 381, Item 319 12641-7)

Architect David Roberts Jr designed the Gooderham Building for the unusually shaped property. It was completed in 1892 and served as the corporate head office for Gooderham & Worts Limited, once Canada’s largest liquor distilling company. Today, the heritage-designated architectural landmark is one of the city’s most photographed buildings and is home to commercial office space and a pub (Toronto Public Library R-6249)

In the archive photo on the left, Grey Line coaches are lined up in front of the Christie, Brown & Company Factory for their picnic. Today, the cookie factory buildings are home to George Brown College St James Campus.
Also notice in the vintage photo the Campbell House at its original location on Adelaide St E (then Duke St), opposite Frederick St. The historic house was moved to 160 Queen St W in 1972 and today is a City of Toronto museum (City of Toronto Archives, Fonds 16, Series 71 Item 5194)





The left side of the archive photo shows the various businesses along the south side of King St W. Nowadays, this stretch is part of Restaurant Row.
On the right side of the archive photo, notice Farb’s Car Wash, which operated from 1953 until the late 1980s. Today, the north side of King St W is home to TIFF Bell Lightbox and condo residences (City of Toronto Archives, Fonds 1257, Series 1057, Item 23)
SOURCE
- City of Toronto Heritage Register
- Heritage Toronto
- Ontario Heritage Trust
- Heritage Toronto: Sackville Street Public School plaque
- The Canadian Contract Record: Volume 4, Number 37, Nov 2, 1893, pg II (Michie & Co, 7 King St W)
- Toronto Star Newspaper Archives: Aug 19, 2000, pgs R1 & R3 (Coghlan Building, 7 King St W)
- The Globe and Mail Newspaper Archives: Nov 6, 1953, pg 25 (King St W & John St, northwest corner)
- The Globe and Mail Newspaper Archives: Sep 7, 2007, pg G10 (King St W & John St, northwest corner)
- The Globe and Mail Newspaper Archives: Sep 4, 2010, pg R7 (King St W & John St, northwest corner)
- Ontario Heritage Trust: 2 Queen St E
- Heritage Toronto: Gooderham “Flatiron” Building 1892 plaque
- Ontario Heritage Trust: York Mechanics’ Institute plaque
- Preliminary Cultural Heritage Evaluation Report: 466-468 Dovercourt Rd by ERA Architects Inc (The Matador Club)
- Photo: Denise Marie for TorontoJourney416
- Vintage Photos: City of Toronto Archives, Toronto Public Library, Archives of Ontario, CNE Heritage & Canadian National Exhibition Association Archives
- Toronto City Directory courtesy of Toronto Public Library
