Looking northeast along Bay St, from just south of Richmond St W, in the Financial District of Toronto.
The streetscape has changed significantly over nearly a century, except for Old City Hall, visible in the background of both photos.
In the right foreground of the archive photo, the Continental Building features a corner storefront that housed a United Cigar store. This building was replaced with an office structure in the early 1960s, which houses Hy’s Steakhouse & Cocktail Bar on the ground floor.
The ornate three-story building with the rounded corner in the centre of the vintage photo was the St. Charles Hotel. Hotelier James O’Neill commissioned the architectural firm Hymes, Feldman & Watson to design this hotel, which replaced a previous establishment with the same name that had once been located at Yonge St and Melinda St. Completed in 1915 at the cost of $100,000, the St. Charles Hotel had 17 guest rooms, dining areas, and a cafe. This short-lived hotel was torn down soon after the archive photo was taken. It was replaced by the current building, constructed for the Robert Simpson department store, designed by architects Chapman & Oxley. Just six months after construction began, according to a newspaper article dated December 7, 1928, the store opened its Bay St entrance. In recent times, it was home to The Bay department store, which closed its doors in June 2025.
The archive photo also shows a two-story structure just north of the hotel. This building originally housed Bowles Lunch for several years before being demolished in the 1960s to make way for Simpson Tower.
Then and Now
SOURCE
- City of Toronto Heritage Register
- Heritage Toronto
- Ontario Heritage Trust
- Biographical Dictionary of Architects in Canada
- The Globe Newspaper Archives: Nov 23, 1912, pg 8 (St. Charles Hotel, looking northeast along Bay St from Richmond St W)
- Construction: Aug 1915, Volume 8, Issue 8, pgs 328-330 (St. Charles Hotel, looking northeast along Bay St from Richmond St W)
- The Toronto Daily Star Newspaper Archives: May 2, 1928, pg 1 (Robert Simpson store, looking northeast along Bay St from Richmond St W)
- The Globe Newspaper Archives: Dec 7, 1928, pg 17 (Robert Simpson store, looking northeast along Bay St from Richmond St W)
- The Globe and Mail Newspaper Archives: Oct 31, 1959, pg 33 (Canadian Imperial Bank of Commerce Building, looking northeast along Bay St from Richmond St W)
- The Globe and Mail Newspaper Archives: Mar 19, 1965, pg B1 (Simpson Tower, looking northeast along Bay St from Richmond St W)
- Photo: Denise Marie for TorontoJourney416
- Vintage Photo: City of Toronto Archives
- City of Toronto: Maps
- Toronto City Directory, courtesy of Toronto Public Library
