A couple of notable buildings appear in both photos, including the Daniel Brooke Building, which is partially visible in the left foreground. This Georgian-style commercial building was constructed in 1833. Over the years, it has housed a variety of businesses, including wholesale and grocery shops, a saddlery and carriage-harness maker, tailors, a dry goods store, an army surplus store, and the Sportsman’s Shop. In the late 1980s, new owners restored the historic building to its original condition. Since then, it has been home to a range of upscale shops and businesses.
The other structure in both photos is the eight-storey red-brick building in the centre-right background. Originally part of the Christie, Brown & Company factory, it was built in 1914 as an addition to serve as the company’s office and additional factory space. In 1971, George Brown College acquired the cookie company’s complex of buildings, and today, the site is the college’s St. James Campus (City of Toronto Archives, Harvey R. Naylor fonds, Fonds 1526, File 73, Item 47)
The archive photo shows, from right foreground to left distance, the Gay Theatre, Cross Service Station, Fire Hall #7, and St. Bartholomew’s Anglican Church.
When the theatre opened in 1913, it was originally called the Bluebell. In the mid-1950s, it was renamed the Gay Theatre, and later became the Parliament Cinema in 1975 before closing in the mid-1980s.
Today, the site where the theatre once stood has been replaced by homes, while the former gas station is now the location of the Regent Park Community Health Centre, which opened in 1999. The fire hall, now known as Toronto Fire Station 325, and St. Bartholomew’s Church are still standing today. Originally built in 1873, the church was located on the east side of River St at Dundas St E. In 1910, it was physically moved to its current location at 509 Dundas St E, which is visible on the far left (City of Toronto Archives, Toronto Planning Board fonds, Fond 2032, Series 841, File 16, Item 6)
Both photos show the Church of the Redeemer on the right. Built in 1879 and designed by architects Smith & Gemmell, the church received heritage status from the city in 1973 and has been a neighbourhood landmark for over 145 years.
The archive photo shows the original location of The Alexandra Gates on Queen’s Park, on the south side of Bloor St W. Also known as the Queen Alexandra Gateway, they were created by the Imperial Order of the Daughters of the Empire, a women’s charitable organization, to commemorate a visit by British royalty—the Duke and Duchess of Cornwall and York—in 1901. The gates are named in honour of Alexandra, who was the Queen Consort at that time. In 1906, the association formally donated the gateway to the city. The gates were relocated twice to make way for road widening and the subway, and in the early 1960s, they were moved to their current location at the north entrance of Philosopher’s Walk on Bloor St W, just west of Queen’s Park, next to the Royal Ontario Museum (City of Toronto Archives, Fonds 200, Series 372, Sub Series 1, Item 1087 – Dept. of Public Works photographs)
The archive photo shows the Rondun Tavern on the right. This establishment was located at 2238 Dundas St W and first appeared in the Toronto City Directory in 1937. The tavern closed its doors in 1985, and the building was demolished shortly thereafter. Since the late 1980s, the site has been occupied by a three-story commercial building.
In the centre background of both photos, the two tall buildings are The Crossways, a residential and commercial complex that was completed in the mid-1970s (City of Toronto Archives, Harvey R. Naylor fonds, Fonds 1526, File 102, Item 19)
The tall building located directly at the corner was constructed in 1915 for the Andrew Muirhead Company, a paint manufacturer. Over the years, it has served various purposes, housing different manufacturing agents and a dressmaker, as shown in the archive photo. Today, this building is part of George Brown College’s St. James Campus and operates as The Chefs’ House, a fine-dining restaurant and event space run by students.
The photos also feature the Patrician Grill, which first appeared in the 1953 Toronto City Directory and was operated by Gus Clowtis. In 1967, the restaurant was purchased by Louie and Helen Papas. It was later taken over by their son, Terry Papas, and his brother-in-law, Chris Slifkas. For over 70 years, the Patrician Grill, known for its cozy booths and a long 50s-style countertop overlooking the kitchen, has been serving traditional homemade diner fare, including breakfast, burgers, and meatloaf, to business people, college students, and locals. The restaurant closed its doors on May 9, 2026 (City of Toronto Archives, Fonds 220, Series 65, File 16, Item 6 – Alexandra Studio photographs)
According to the 1893 Toronto City Directory, a few of the establishments in the archive photo, from right to left, include R. Reilly hats & furs, D. Merrick millinery & dressmaking, Dominion Express, S. Tidy & Son florist, Dominion Pharmacy, Kent Bros. jewelers, John Wanless jewelers, and Robert Simpson dry goods. Also notice the sign painted on the side of the building once at 164 Yonge St for the Carbolic Smoke Ball Co., which operated from the building in the late 1880s.
Shortly after the archive photo was taken, Robert Simpson built his “departmental” store at the southwest corner of Yonge St and Queen St W. The store was open for only a short time before it was completely destroyed by fire in 1895. The commercial building, designed by architects Burke & Horwood, was reconstructed and reopened in January 1896. Gradually, the Robert Simpson Co. store expanded, occupying more of the block, with additions made from 1900 through circa 1970. In 1973, the building was added to the city’s heritage register. In 1978, the Hudson’s Bay Company acquired the property, which extends to Bay St. In 1991, this location transitioned from Simpsons to The Bay. The Bay, which also housed Saks Fifth Avenue, closed its doors in June 2025 (Toronto Public Library Pictures-R-1630)
The archive photo was taken for the TTC to document the facades of retail and commercial establishments on Yonge St during underpinning for the construction of the Yonge Street Subway, today known as Line 1 or the Yonge–University Line. It also shows the streetcar line that once ran along Yonge St. A few of the establishments on the right in the old photo include the Silver Grill, Biltmore Theatre, Disney Shop (men’s wear), Olympia Bowling & Billiards, Le Coq d’Or Tavern and New Empress Grill in the Edison Hotel.
Since 2007, the northeast corner has been home to what is now known as The Tenor, a retail, office, and entertainment complex. The large building with the glass facade in the centre background of the present-day photo is the Sheldon & Tracy Levy Student Learning Centre at Toronto Metropolitan University (City of Toronto Archives, Fonds 16, Series 574, File 13, Item 49320 – Brigdens Limited photography)
The archive photo shows the entrance of Cinecity Cinema on the left in the former Postal Station F, with the Fotomat Kiosk on the right (City of Toronto Archives, Harvey R. Naylor fonds, Fonds 1526, File 2, Item 4)
The archive photo shows several notable buildings, arranged clockwise starting in the lower left corner: Eaton’s College Street store, the Canadian Bank of Commerce in the castle-like building (which was originally home to the Independent Order of Odd Fellows, or IOOF), the construction of the Westbury Hotel, and the S.S. Kresge Co. store.
Today, the former Eaton’s store is known as College Park. The castle-like building now serves as office and commercial space, while the Westbury Hotel has been converted into a Courtyard by Marriott. The location where Kresge’s once stood has been replaced by The Ellington, a mixed-use building featuring both residential and commercial spaces (Toronto Public Library Pictures-R-4023 – James Victor Salmon photographer)
The archive photo shows Café New Orleans (City of Toronto Archives, Ellis Wiley fonds, Fonds 124, File 8, Item 139)
The archive photo shows the corner building when the storefront was a Royal Bank branch. The short-lived RBC branch appears in the Toronto City Directory from 1988 to 1992.
The original building, constructed between 1895 and 1896, was home to the Philip Jamieson & Company clothing store. Designed in the Renaissance Revival style by the architectural firm Curry, Baker & Co., the building featured a unique rounded corner, a suggestion made by Mr. Jamieson to improve traffic flow. This distinctive design element was prominently highlighted in many of the store’s advertisements, which included the phrase “The Rounded Corner – Queen and Yonge Sts.” In 1909, Mr. Jamieson sold both the building and the land lease.
From 1912 until the mid-1970s, the building housed an F.W. Woolworth store. In 1970, the exterior was clad in porcelain-finished aluminum and Woolworth’s new colours, white and blue. During the 1980s, architect Lloyd Alter’s heritage conservation efforts led to the removal of some of this cladding, exposing the original brick underneath, as shown in the archive photo. After RBC left the building, the storefront served as various retail establishments, including Tower Records, Coast Mountain Sports, Atmosphere, and SportsChek.
In 2018, major restoration work began to transform the building into a high-end retail space connected to the Eaton Centre. Although the plan was to salvage and restore much of the original structure, it had deteriorated beyond repair due to decades of wear and the overcladding. ERA Architects and Zeidler Architecture collaborated on restoring the terracotta and masonry façade, reconstructing it with over 40,000 replica bricks, stones, and terracotta pieces (City of Toronto Archives, Ellis Wiley fonds, Fonds 124, File 3, Item 150)
The archive photo shows various buildings that once stood near the corner of two streets, along with pedestrians on the sidewalk, a portion of a horse pulling a wagon, and a boy in the street. The wood-frame building directly at the corner, which housed Rocco Gianvecchio’s grocery store at the time, was originally Crispin’s Tavern, which operated from around 1830 to the 1840s.
The left side of the vintage photo also features a billboard for Heuther’s Wuerzburger lager, produced by the Lion Brewery in Waterloo, Ontario. In the centre and right background, the taller building was home to the Reliance Moulding Co. Limited.
In the early 1940s, the wooden buildings at the corner, including the former tavern, which was over 110 years old, were demolished and replaced with a parking lot. The factory building was torn down in the 1960s. In 1972, the Four Seasons Sheraton Hotel, now known as Sheraton Centre Toronto, opened on the block (Toronto Public Library E8-215)
The historic, world-renowned music venue Massey Hall was established in 1894, when industrialist Hart Massey built it as a gift to the people of Toronto to promote the arts. The archive photo shows Massey Hall with a “moustache” style fire escape, a safety feature installed on the front and sides of the building in 1911 at a cost of approximately $5,000.
Throughout the decades, the venue has undergone several updates. From 2018 to 2021, the historic hall closed for significant restoration inside and outside the building. On the exterior, this project included removing the iron stairs and restoring the brick and masonry. A team of experts worked on restoring the “MASSEY MUSIC HALL” limestone letters, sourcing matching stone to recreate some of the damaged letters. Originally, the pediment featured intricately carved stone reliefs of an orchestra and musical instruments, which had disappeared or deteriorated over the years. Careful attention was given to this area to remove paint and reveal the shadows of the orchestra carvings.
Today, the state-of-the-art performance venue, which includes a new 7-storey tower and the historic music hall, is collectively called Allied Music Centre. The expanded facility features four performance venues, a recording studio and creative workspaces (City of Toronto Archives, Fonds 200, Series 1465, File 427, Item 12 – Urban Design photographs)
SOURCE
- City of Toronto Heritage Register
- Heritage Toronto
- Heritage Toronto: Daniel Brooke Building plaque (looking northeast along King St E from Jarvis St)
- Ontario Heritage Trust
- Ontario Heritage Trust: 200 King St E (Christie, Brown & Company Factory, looking northeast along King St E from Jarvis St)
- Ontario Heritage Trust: 160-178 Yonge St (Robert Simpson Co., northwest corner of Yonge St & Richmond St W)
- Ontario Heritage Trust: 178 Victoria St (Massey Hall, looking southeast across Shuter St)
- National Historic Site of Canada: Massey Hall (Looking southeast across Shuter St)
- Toronto Star Newspaper Archives: Jul 24, 1987, pg C1 (Daniel Brooke Building, looking northeast along King St E from Jarvis St)
- The Globe Newspaper Archives: Oct 11, 1901, pg 2 (Alexandra Gates, looking northeast towards Bloor St W and Avenue Rd from Queen’s Park)
- The Globe Newspaper Archives: Nov 22, 1906, pg 9 (Alexandra Gates, looking northeast towards Bloor St W and Avenue Rd from Queen’s Park)
- Plaques placed by the University of Toronto along Philosopher’s Walk (Alexandra Gates, looking northeast towards Bloor St W and Avenue Rd from Queen’s Park)
- The Toronto Star Newspaper Archives: Sep 4, 1999, pg J3 (Regent Park Community Health Centre, looking southeast at Dundas St E & Parliament St)
- The Toronto Star Newspaper Archives: Feb 14, 1976, pg C8 (The Crossways, looking northeast up Dundas St W towards Bloor St W)
- The Toronto Star Newspaper Archives: Mar 30, 1985, pg A12 (Rondun, looking northeast up Dundas St W towards Bloor St W)
- The Globe Newspaper Archives: Aug 11, 1888, pg 12 (Carbolic Smoke Ball Co., northwest corner of Yonge St & Richmond St W)
- The Globe Newspaper Archives: Mar 4, 1895, pg 1 (Robert Simpson Co., northwest corner of Yonge St & Richmond St W)
- The Globe Newspaper Archives: Nov 21, 1896, pg 13 (Robert Simpson Co., northwest corner of Yonge St & Richmond St W)
- The Globe and Mail Newspaper Archives: Jun 6, 1991, pg B1 (Simpsons/The Bay, northwest corner of Yonge St & Richmond St W)
- The Globe Newspaper Archives: Jul 24, 1895, pg 8 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- The Globe Newspaper Archives: Mar 2, 1896, pg 7 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- The Globe Newspaper Archives: Feb 2, 1909, pg 1 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- The Globe Newspaper Archives: Feb 22, 1909, pg 5 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- The Globe and Mail Newspaper Archives: Mar 24, 1970, pg B1 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- Canadian Architect and Builder, Volume 9, Number 1, Jan 1896, pg 14 (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- St. Bartholomew’s Anglican Church: History (St. Bartholomew’s Church, looking southeast at Dundas St E & Parliament St)
- ERA Architects: 2 Queen Street West (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- Zeidler Architecture: 2 Queen West (Philip Jamieson & Co., northwest corner of Queen St W & Yonge St)
- Landmarks of Toronto: Volume 1 by J Ross Robertson (1894), pgs 464-466 (Crispin’s Tavern, northeast corner of Richmond St W & York St)
- The Globe Newspaper Archives: Oct 29, 1902, pg 10 (Heuther’s Wuerzburger lager, northeast corner of Richmond St W & York St)
- The Globe and Mail Newspaper Archives: Dec 23, 1941, pg 6 (Crispin’s Tavern, northeast corner of Richmond St W & York St)
- The Globe Newspaper Archives: Mar 28, 1911, pg 8 (Massey Hall, looking southeast across Shuter St)
- The Globe Newspaper Archives: Apr 12, 1911, pg 8 (Massey Hall, looking southeast across Shuter St)
- Atwill-Morin: Massey Hall (looking southeast across Shuter St)
- Massey Hall & Roy Thomson Hall: About Us (looking southeast across 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
