A few of the establishments in the archive photo, from right to left, include Home of the Gourmet, Net Discount, John Richardson needle worker, Charcoal Broil Burgers, Wingate Clothing Exchange, Parkside Tavern, Bill & Matt’s Variety & Snack Bar and Tuxedo Junction formal rentals. In both photos, notice the St Charles Tavern clock tower in the distance (City of Toronto Archives, Harvey R. Naylor fonds, Fonds 1526, File 2, Item 68)
The archive photo shows the TTC loop on the left and The Evening Telegram building in the centre background. The right side of the vintage photo features Dominion Bank, Rexall Drugs and C & P Grill (City of Toronto Archives, Alexandra Studio fonds, Fonds 1257, Series 1057, Item 2046)
The archive photo shows the streetscape from over a century ago, featuring the streetcar tracks that once ran along the two streets. A constant in both photos is the building on the left. Constructed in 1911 for the Bank of Toronto, it served as a branch of the Toronto Dominion Bank until the 1980s. Since then, this heritage-designated building’s storefront has had various commercial uses, and today, it’s home to a dental office (City of Toronto Archives, Fonds 16, Series 574, File 71, Item 2781 – Brigdens Limited photography)
The archive photo shows the streetscape from over a century ago, including the houses and buildings that once lined the two streets. At that time, this section of Bay St was known as Teraulay St, and Albert St extended west of Bay St all the way to Osgoode Hall. The office building with the smokestack on the left was called Manning Chambers, while the house directly at the corner operated as a Chinese laundry. The building on the right housed various businesses, including Gundy-Clapperton Co., which specialized in cut glass.
The dwellings near the corner were torn down and replaced by Shea’s Hippodrome, a 2,800-seat theatre, which opened in 1914. The theatre closed in 1956. Following its closure, the theatre and other structures on the block were demolished to make way for a projected civic square. On September 13, 1965, Nathan Phillips Square officially opened and was inaugurated along with the new Toronto City Hall (City of Toronto Archives, William James Family fonds, Fonds 1244, Item 7306)
A few of the establishments in the archive photo, from left to right, include Rubinoff & Sons men’s and women’s clothing (which was later the location of The Velvet Underground and, as of May 2026, is home to HYVE nightclub), Princess Fashion Furs, Hykel Men’s Wear & Shoes, and Haba’s Grill (City of Toronto Archives, Fonds 200, Series 372, Sub Series 100, Item 338 – Dept. of Public Works photographs)
The building in the archive photo was originally constructed for the Bank of Hamilton between 1902 and 1903, designed by architect George W. Gouinlock. Following the merger of the Bank of Hamilton and the Canadian Imperial Bank of Commerce in 1924, the building continued to serve as a CIBC branch, as shown in the vintage photo on the right, along with the shops and businesses that once occupied the ground floor.
The building’s red-brick facade, visible in the present-day photo supported by yellow retention towers, is being preserved for the entrance to the future Queen-Spadina Station on the Ontario Line (City of Toronto Archives, Toronto Planning Board fonds, Fonds 2032, Series 841, File 47, Item 27)
The building at the corner, constructed in 1913, was originally The Sterling Bank of Canada. It later became CIBC and eventually housed Pizza Pizza. The current photo shows the heritage-designated former bank building, whose storefront is home to Taco Bell, integrated into the modern 252 Church condo tower.
The archive photo also features the steeple of St. Michael’s Cathedral Basilica in the left background, while the curved structure in the right background is the east tower of City Hall (City of Toronto Archives, Toronto Planning Board fonds, Fonds 2032, Series 841, File 51, Item 18)
The archive photo features the Dominion Hotel at 500 Queen St E. Built between 1889 and 1890, the hotel was originally part of the neighbouring Dominion Brewery, today known as Dominion Square, which was founded by Robert Davies in the 1870s.
The Dominion Hotel was designed by architect David Roberts Jr. and was originally four stories tall. At some point, a fire damaged the upper part of the building, leading to several changes, including the removal of the top floor and the top of the corner tower.
In 2024, ERA Architects completed a redesign of the storefront inspired by the building’s original design. They also rehabilitated the stone and masonry above. Today, the storefront of the heritage-designated building is home to a restaurant (City of Toronto Archives, Alexandra Studio fonds, Fonds 1257, Series 1057, Item 521)
Both photos feature Old City Hall and its clock tower. This magnificent building, designed by architect E.J. Lennox, took 11 years to complete and was officially opened in 1899. Its clock tower reaches a height of 87 meters (285 feet) to the top of the spire.
In the background of the archive photo, you can also see the former Eaton’s store building, which was replaced by the Eaton Centre that opened in 1977 (City of Toronto Archives, Harvey R. Naylor fonds, Fonds 1526, File 83, Item 1)
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 (City of Toronto Archives, Globe and Mail fonds, Fonds 1266 Item 13143)
A few of the establishments in the archive photo, from left to right, include the Dominion Bank, Municipal Hotel, Osgoode Restaurant, Union Hotel and the Broadway Theatre. The four-storey, half-timbered Tudor Revival building with the Teperman Wrecking sign is the Hamilton Trust Building, constructed around 1915. The vintage photo shows the building shortly after a 3-alarm fire had roared through it.
In 1965, this block—located directly across from Nathan Phillips Square and described by a local newspaper writer as a “ramshackle row”—was demolished to make way for redevelopment. Today, this area is home to the TD Bank, the Thomson Building, and the Sheraton Centre Toronto Hotel (City of Toronto Archives, Ellis Wiley fonds, Fonds 124, File 1, Item 102)
The archive photo shows the corner as it looked over a century ago. A year after the vintage photo was taken, the buildings on the corner were torn down and replaced, except the four-storey brick building on the left, which faces Yonge St (with the Empire Wall Paper sign). Completed in 1914 at a cost of $250,000, it was extended to the corner, heightened by one storey, and modified to match the design of the new building. Architects Burke, Horwood & White designed it for James Ryrie, a Toronto jeweller. The ground floor was for shops, while the upper floors served as office space, a role the heritage-designated building continues to serve today (City of Toronto Archives, William James Family fonds, Fonds 1244, Item 497)
The building in the right foreground, shown as Catto’s in the archive photo, was constructed in 1886. Initially a commercial building, it was later home to the Yonge Street Mission, followed by various theatres. When Catto’s took over the building in 1920, they retained the theatre’s overhang and repurposed the sign to feature the store’s name. The shop, which specialized in fine linens and dry goods, was founded on King St E in 1864 (where the King Edward Hotel stands today) by John Catto, who was born in Scotland. After Mr. Catto passed away in 1928 at the age of 96, the store continued to operate for five more years before closing in 1933. Currently, the building’s storefront houses easyfinancial Services.
The taller building in the centre is called the Ryrie Building and was constructed in two phases from 1891 through 1914. The archive photo shows this building’s corner storefront when it housed the Toronto Hydro Electric Shop. Today, that same storefront is home to Sweat & Tonic.
Another item to point out is the tall sign in the far left distance of the vintage photo for the Imperial Theatre. Today, it’s known as the CAA Ed Mirvish Theatre, and it features a similarly shaped sign visible in the present-day photo (City of Toronto Archives, Fonds 1257, Series 1057, Item 45)
Bacchus Steakhouse & Tavern, shown in the archive photo, opened in 1971 and was known for its generous portions of steak and seafood, alongside live piano music. One of its charming features was the cozy Fireplace Room, while the tavern was located downstairs. Bacchus Steakhouse & Tavern was short-lived and closed in the early 1980s.
The building dates back to the mid-1880s and was originally the home of the Quebec Bank. There are plans for new development at the site that will preserve the heritage-designated building (City of Toronto Archives, Toronto Planning Board fonds, Fonds 2032, Series 841, File 69, Item 20)
The building featured in the right foreground of the photos was constructed in two phases between 1891 and 1914. Known as the Ryrie Building, the archive photo shows when its corner storefront was home to the Silver Rail Tavern, a cocktail lounge and restaurant that opened in 1947. The tavern was famous for having the city’s longest bar—a 90-foot stretch with 40 seats—and featured a silver railing beside the staircase that led to the downstairs dining room. After more than 50 years of operation, the legendary Silver Rail Tavern closed its doors in 1998. Today, the corner storefront is occupied by Sweat & Tonic.
Both photos also show the Eaton Centre on the left and fire hydrants located diagonally at the corners (City of Toronto Archives, Fonds 200, Series 1465, File 617, Item 9 – Urban Design photographs)
SOURCE
- City of Toronto Heritage Register
- Heritage Toronto
- Ontario Heritage Trust
- Ontario Heritage Trust: 60 Queen St W (Old City Hall, looking east along Queen St W towards Bay St)
- Ontario Heritage Trust: 2854 Dundas St W (Bank of Toronto, looking northeast along Dundas St W, west of Keele St)
- Biographical Dictionary of Architects in Canada
- The Globe and Mail Newspaper Archives: Jul 24, 1946, pg 4 (TTC loop, looking southeast at Dupont St & Christie St)
- The Globe and Mail Newspaper Archives: Dec 28, 1956, pg 5 (Shea’s Hippodrome, looking southwest at Bay St from Albert St)
- The Globe and Mail Newspaper Archives: Apr 8, 1963, pg 5 (Hamilton Trust Building, looking southwest along Queen St W from Bay St)
- The Globe and Mail Newspaper Archives: Jul 21, 1965, pg 27 (looking southwest along Queen St W from Bay St)
- The Toronto World Newspaper Archives: Apr 12, 1890, pg 1 (Dominion Hotel, northwest corner of Queen St E & Sumach St)
- ERA Architects: The Historic Dominion Hotel (Dominion Hotel, northwest corner of Queen St E & Sumach St)
- CIBC: 150 Years – A short story PDF dated 2017 (Bank of Hamilton/CIBC, looking southeast at Spadina Ave & Bulwer St)
- Metrolinx: Building the Ontario Line… (Bank of Hamilton/CIBC, looking southeast at Spadina Ave & Bulwer St)
- The Globe and Mail Newspaper Archives: Jun 19, 1971, pg 27 (Bacchus Steakhouse, northwest corner of King St E & Toronto St)
- The Toronto Star Newspaper Archives: Jul 4, 1983, pg A11 (Bacchus Steakhouse, northwest corner of King St E & Toronto St)
- 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)
- The Globe Newspaper Archives: Jan 30, 1913, pg 8 (Ryrie Building, northeast corner of Yonge St & Shuter St)
- The Globe Newspaper Archives: Apr 22, 1933, pg 10 (Catto, looking northeast along Yonge St from south of Shuter St)
- The Globe Newspaper Archives: Sep 8, 1928, pg 17 (Catto, looking northeast along Yonge St from south of Shuter St)
- The Globe and Mail Newspaper Archives: Apr 2, 1947, pg 15 (Silver Rail, looking north along Yonge St from Shuter St)
- The Globe and Mail Newspaper Archives: Jun 25, 1998, pg A12 (Silver Rail, looking north along Yonge St from Shuter 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
