
Once home to 4D’s Diner and later Flo’s Diner, the restaurant was demolished in the early 2000s to make way for the present-day mixed-use building. On Flo’s last day at that location in April 2000, the staff celebrated by dressing in 1950s clothing to thank their customers. They relocated to the 2nd floor of 70 Yorkville Ave. Flo’s closed in March 2024 (City of Toronto Archives, Fonds 200, Series 1465, File 43, Item 49 – Urban Design photographs)

According to the 1883 Toronto City Directory, some of the establishments shown in the archive photo include P. Jamieson, a clothier; Kennedy & Fortier, which specialized in boots and shoes; and Mrs. W. Bilton, who sold fruits, all located on the left side. On the right side, there are J. Harte & Co., which dealt in stoves; R. Platts, a tailor; and C.M. Henderson & Co., auctioneers.
The old photo also shows the horsecars that once travelled along Yonge St (City of Toronto Archives, Fonds 1478, Item 38 – F.W. Micklethwaite photographs)

The archive photo shows the Rialto Theatre, once located at 219-221 Yonge St (City of Toronto Archives, Fonds 1231, Item 2216 – James Victor Salmon photographer)

Taken for the city’s Traffic Study Department, the caption below the archive photo reads: “Traffic on Yonge St, looking north from the south side of Queen St. Congestion stretches as far as the eye can see, with a solid line of curb-parked cars. Time: 3:26 p.m., Friday, Dec. 20, 1935.”
The old photo also features the F.W. Woolworth store on the left and Loew’s Theatre in the distance on the right, along with the streetcars that once travelled along Yonge St.
In the present-day photo, the facade of the building that once housed Woolworth’s was reconstructed using replica bricks, stones, and terracotta pieces due to deterioration and is now part of the Toronto Eaton Centre. Loew’s Theatre is today known as the Elgin & Winter Garden Theatres (City of Toronto Archives, Fonds 16, Series 71, Item 11702 – Alfred Pearson photographer)

The archive photo shows the streetscape from nearly 100 years ago, with a constable on point duty at the intersection and the streetcar line that ran along Bay St. It also shows the buildings that once occupied the corner, including the Hotel Widmer, which were being boarded up for demolition. The hotel was listed in the Toronto City Directory from 1911 to 1927.
In the same year that the vintage photo was taken, property developers Yolles & Rotenberg constructed Sterling Tower at the site. This 22-storey office building, designed in the Art Deco style by architects Chapman & Oxley, was added to the city’s heritage register in 1976 (City of Toronto Archives, Alexander W. Galbraith fonds, Fonds 1568, Item 234)

The archive photo shows Glass Buckette Restaurant Nite Club at the corner. Notice the Sutton Place Hotel in the background (City of Toronto Archives, Fonds 200, Series 1465, File 604, Item 7 – Urban Design photographs)

The archive photo shows the former Temple Building, the tall structure in the centre background, and the former Colonial Theatre in the left foreground (City of Toronto Archives, William James Family fonds, Fonds 1244, Item 515)

The archive photo features The Mail and Empire Building, shown directly at the corner. Constructed between 1879 and 1881, the structure was initially known as the Mail Building, where The Toronto Daily Mail newspaper was printed and published. Designed by architect Richard Waite in the French Renaissance style, the five-storey building featured a 40-meter (130-foot) tower where, on a clear day, “the American shore could easily be discerned.” During that first decade, the building suffered fire damage on three separate occasions, with one blaze severely damaging the top floor, which had to be reconstructed.
In 1895, The Mail merged with The Empire newspaper to form The Daily Mail and Empire newspaper, whose sign is visible in the old photo. In 1936, The Globe newspaper absorbed The Mail and Empire, which then became known as The Globe and Mail.
Two years later, in 1938, the grand newspaper building was sold to the Bank of Montreal. The following year, it was demolished to make way for a 16-storey structure that served as the bank’s main office and Ontario headquarters. This building remained until 1975, when it too was torn down to make way for the current two-storey Bank of Montreal building, which is part of First Canadian Place at 100 King St W (City of Toronto Archives, Fonds 1231, Item 2037 – James Victor Salmon photographer)


A few of the establishments in the archive photo, from left to right: Linenhall (which sold linen goods), Uptown Dollar Taxi, Chinese Laundry, E. Bailey & Co. (cleaners and dyers), the Imperial Bank of Canada, and, across Yonge St, Stollery’s Menswear. The old photo also shows the streetcar tracks that once ran along Bloor St (City of Toronto Archives, Fonds 200, Series 372, Sub Series 3, Item 647 – Dept. of Public Works photographs)

The photos show the Church of the Redeemer, which was built in 1879. Designed by architects Smith & Gemmell in the English Gothic style, the Anglican church features a distinctive bell gable. The church was added to the city’s heritage register in 1973 and has been a neighbourhood landmark for over 145 years.
In the archive photo, notice the constable on point duty directing traffic at the intersection (City of Toronto Archives, Fonds 1231, Item 349 – James Victor Salmon photographer)

The archive photo shows the streetscape from over 90 years ago, prominently featuring Oddfellows Hall at the corner. Constructed between 1891 and 1892, the four-storey castle-like building was designed by architects Dick & Wickson for the International Order of Oddfellows (IOOF). In its early years, the building housed shops, offices, and a branch of the Canadian Bank of Commerce on the lower floors, with Oddfellows Hall located above.
In 1910, the Bank of Commerce purchased the land and building for $137,000, and in 1931, the ground floor was altered for the bank. In 1974, the city added the landmark to the heritage register. The CIBC last appears at this address in the 1996/97 Toronto City Directory. By the late 1990s, the building’s corner storefront became home to Starbucks, which operated there until 2021. Today, the building continues to house commercial and office space.
In the left background of both photos, there are two other heritage-designated buildings that still stand today. The first is what was originally the Upper Canada Bible Society at 14 College St, and the second is Canadian Foresters’ Hall at 22 College St, both constructed in 1910 (City of Toronto Archives, Fonds 200, Series 372, Sub Series 66, Item 52 – Dept. of Public Works photographs)



SOURCE
- City of Toronto Heritage Register
- City of Toronto Heritage Register: 14 College St (Upper Canada Bible Society, looking northwest from Carlton St towards Yonge St & College St)
- City of Toronto Heritage Register: 22 College St (Canadian Foresters’ Hall, looking northwest from Carlton St towards Yonge St & College St)
- Heritage Toronto
- Ontario Heritage Trust
- Ontario Heritage Trust: 162 Bloor St W (Church of the Redeemer, northeast corner of Bloor St W & Avenue Rd)
- Ontario Heritage Trust: 450 Yonge St (Oddfellows Hall, looking northwest from Carlton St towards Yonge St & College St)
- The Toronto Daily Star Newspaper Archives: Jan 14, 1928, pg 25 (Sterling Tower, southwest corner of Bay St & Richmond St W)
- The Toronto Daily Mail Newspaper Archives: Jul 2, 1881, pg 1 (Mail Building, northwest corner of King St W & Bay St)
- The Globe Newspaper Archives: May 26, 1884, pg 5 (Mail Building, northwest corner of King St W & Bay St)
- The Globe Newspaper Archives: May 24, 1886, pg 8 (Mail Building, northwest corner of King St W & Bay St)
- The Globe Newspaper Archives: Nov 19, 1936, pg 1 (Mail and Empire Building, northwest corner of King St W & Bay St)
- The Globe and Mail Newspaper Archives: Jul 26, 1938, pg 1 (Mail and Empire Building, northwest corner of King St W & Bay St)
- The Globe and Mail Newspaper Archives: Dec 6, 1938, pg 18 (Mail and Empire Building, northwest corner of King St W & Bay St)
- The Globe and Mail Newspaper Archives: Oct 26, 1976, pg 5 (Bank of Montreal Building, northwest corner of King St W & Bay St)
- Zeidler Architecture: 2 Queen West (F.W. Woolworth, looking north up Yonge St from Queen St)
- The Globe Newspaper Archives: Mar 24, 1910, pg 2 (Oddfellows Hall/CIBC, looking northwest from Carlton St towards Yonge St & College St)
- Photos: Denise Marie for TorontoJourney416
- Vintage Photos: City of Toronto Archives, Toronto Public Library, Archives of Ontario & CNE Heritage
- City of Toronto: Maps
- Toronto City Directory, courtesy of Toronto Public Library
