herr2ck: Toronto Trip, pt. 4

August 2025.

Yonge Street in Toronto is pretty common herr2ck fare--historic commercial buildings in an urban area. Toronto’s numerous urban renewal initiatives make these kinds of streets rather uncommon, compared to Montreal, which simply expanded its downtown to a formerly residential area and retained its historic “Old Montreal”. We’ll start at Yonge Street’s intersection with Shuter Street and proceed southward from there.

Ryrie Building

The corner of Yonge Street and Shuter Street, showing the 1891 building and 1899 portion before the two were combined. (Lost Toronto)

Toronto is 8 hours from Chicago, but the latter’s influence on early skyscrapers was felt across America. My sources are inconsistent and rather unclear about how exactly the building came about. My understanding is that the earliest portion of the Ryrie Building dates to 1891 and appeared to be a simple Italianate or Commercial style design. The first phase of the existing building was completed in 1899, consisting of the northern four bays. It is an earlier example of Beaux-Arts architecture with Chicago School characteristics and was designed by either Langley & Burke or Horwood & Burke. The fifth floor is an addition dating to 1914 by Horwood & White, and the building was also extended to the corner of Yonge and Shuter, incorporating the 1891 building into its structure.

Historic photo of the completed building. (ERA Architects)

The Ryrie Building was built for Ryrie Brothers Jewelers, which was the largest jeweler in Toronto by 1900. They were eventually acquired by Henry Birks & Sons. The most notable tenant of the Ryrie Building was the Silver Rail Restaurant, which opened in 1947. It was known for its 110-foot long bar clad in chrome and neon lights, and the silver banister on the stairs that connected it to the basement, where the restaurant got its name.

Snazzy mid-century storefront of the Silver Rail restaurant. (Ontario Archives)

By the 1950s, the building’s cornice was removed, and the base was re-clad in shiny terra-cotta or tile. It was restored by ERA Architects between 1997 and 2005, which removed the altered storefront but did not recreate the cornice. The Silver Rail closed in 1998, and the commercial base has had various tenants since.

I wish I had spent a little more time on this one, as the vaulted windows and pilasters are pretty interesting.

Former Bank of Toronto Branch

A partial elevation of the building drawn by Lennox. (Wikimedia)

I really love this tiny Beaux-Arts bank. It was designed by prominent Toronto architect Edward J. Lennox as a branch of the Bank of Toronto and completed in 1905. Despite its tiny, square plan, the building is very vertical and lavishly decorated with Corinthian columns and patterns.

The bank eventually closed, and in 1975 it was listed on the Canadian Register of Historic Places. By that time, the tenant was the Toronto Historical Board, which eventually became Heritage Toronto and moved out in 1998. It was being renovated in the late 2010s, and it is currently occupied by a wealth management company.

Detail of the elaborate cornice and pediment:

Entrance portal:

The contemporary building next door (Massey Tower) is set back from the sidewalk, making the very shallow plan visible. Also note the small dome on top, possibly marking influence from the Pantheon.

Massey Tower (Former Canadian Bank of Commerce Branch)

Massey Tower is a 62-story residential skyscraper that was completed in 2019 by Hariri Pontaniri Architects. Its base incorporates a 1905 Canadian Bank of Commerce branch designed by Darling & Pearson. The bank itself was listed as a heritage property by the city of Toronto in 1974, and the branch closed in 1987. The building was sooty and in poor repair by the 2010s, but it was restored and gutted for use by the Massey Tower project.

Simpler than its neighbor of the same vintage, the facade is also a temple-front, though this one uses the Ionic order and two large pilasters at the corners. Two large shields at either end bear the bank’s year of establishment and this building’s construction.

Detail of the pediment and entablature:

Heintzman Building (J. F. Brown Furniture Building)

A Chicago School design, as indicated by its expression and three-part windows, this one was built in 1903 by Henry Simpson. In 1910, it was altered for T. Heintzman Co., a piano company, earning it a new name. The company used it as a showroom and rented out the office space above. Its base has been altered, and the windows are modern replacements. Heintzman moved out in 1971.

Elgin & Winter Garden Theatres

Historic photo of the theater, looking north on Yonge Street. See if you can spot some buildings I took photos of earlier. (Ontario Heritage Trust)

This theater complex’s Yonge Street facade is deceptively small, and it actually has quite the history. Unfortunately, I only took one picture. The Elgin & Winter Garden Theatres are the only surviving “stacked theaters” in the entire world, a method of confining two separate theaters in one building. The Renaissance Revival building dates to 1913 and was designed by noted theater architect Thomas W. Lamb.

Left: The Elgin Theatre. Right: The Winter Garden Theatre. (Wikimedia)

The theater was built for Loew’s Theatres and intended to show both late vaudeville shows and early silent movies. The theater closest to the ground floor (the Elgin today) was known as Loew’s Yonge Street Theatre upon completion, and despite its pretty fanciful Renaissance Revival interior, it was intended for lower and middle-class patrons. The upper theater was themed to appear as a garden during sunset, complete with faux trees, painted decor, and hanging lanterns. Its seats could be reserved by upper-class theater attendees.

In 1928, the Elgin Theatre was converted to play “talkies” (early sound films), and the Winter Garden Theatre was closed. It sat untouched for decades, allowing the preservation of the leftover vaudeville set decorations. Loews continued to operate the theater until 1969, when it was sold to Famous Players. As was pretty common for the lavish movie palaces of the early 20th century, the owners resorted to showing B-movies and adult films in order to stay in business.

The Ontario Heritage Foundation purchased the theater in 1981, though it closed later that year. In 1982, it was listed as a National Historic Site of Canada. The theater’s preservation was ensured through a highly attended showing of Cats from 1985-1987, and it was restored between 1987 and 1989. The twin theaters remain in use today.

2 Queen Street East

The 2 Queen Street East skyscraper incorporates this Beaux-Arts BMO branch from 1910 in its base. It’s less temple-front-y and has a more rectangular expression, only suggesting columns and not overtly placing them.

Hudson’s Bay Building

1891 photo of the original Simpson’s store. (Wikimedia)

You might have noticed that until now, I focused on the east side of Yonge Street. Today, the west side of Yonge Street between Dundas Street and Queen Street is entirely consumed by the massive Postmodern Eaton Centre, which replaced Simpson’s/Hudson’s Bay’s competitor, the Eaton’s department store (of course back then it was a complex of individual buildings). However, the Hudson’s Bay Building survives and hearkens back to this area’s original look.

Early photo of the building’s original appearance. Love the Chicago Temple-esque building next door with a spire slammed on top. (Wikimedia)

The building’s history can be traced to 1872, when Robert Simpson founded a dry goods store in Toronto after a previous store in Newmarket burnt down. By the 1890s, Simpson’s store had grown such that he commissioned a larger one, which burned in 1895 just three months after it opened. Simpson commissioned Burke & Horwood to redesign a fireproof store building, which was ultimately completed in a union of Chicago School forms and structural expression with Renaissance Revival ornamentation. This building stands today and was completed in 1896.

c. 1908 postcard of the building after its first addition in 1907.

As is pretty common for major department stores in large cities, the building was expanded many times as Simpson’s grew. The first addition occurred in 1907, when two similarly designed wings were added to the west and south faces of the original building. A second addition was completed in 1923, ostensibly the two bays between the 1907 addition and 1929 addition that faces Bay Street. Both of these additions were designed by Burke & Horwood as well.

Toronto Symphony Orchestra inside Arcadian Court in 1929. (City of Toronto Archives)

In 1929, a nine-story Stripped Classical addition designed by Chapman & Oxley was added to the Bay Street end of the building, expanding it to span two city blocks. It includes the Art Deco-styled Arcadian Court inside. In 1969, the Simpson Tower was completed on the northwest corner of the site, which was a Brutalist design by John B. Parkin. (It has since been reclad with a contemporary skin.)

Hudson’s Bay purchased Simpson’s in 1978, but allowed the stores to operate under their original name until the 1990s. In this building’s case, it became The Bay in 1991. It essentially operated as it had before until 2016, when the interior was subdivided to incorporate a Saks Fifth Avenue (which Hudson’s Bay had also acquired). As was the case with the Bay Building in Montreal, this building also closed in 2025 due to the bankruptcy of Hudson’s Bay.

Oh yeah…this is a classic Chicago School department store, not unlike Marshall Field’s in Chicago. Short, wide Renaissance-y block with highly regular fenestration. I wanted to cover the north side, but this massive steel implement was in my way:

The corner pilaster has an elaborately carved pilaster with the street name and “RS” for Robert Simpson:

One of the lavishly decorated vaulted windows, which date to the 1900 addition:

Loving all the different ornamental borders and the texture they achieve.

Detail of the very regular, rectangular windows:

Confederation Life Building

1892 photo of the Confederation Life Building with original base. (Archives of Ontario)

This fanciful Romanesque Revival building was built for the Confederation Life Insurance Company, which was founded in 1871. In 1889, they held an architectural competition, and the firm Knox, Elliot, & Jarvis was selected. Its construction began a year later. Upon completion in 1893, it was the tallest building in Toronto. As it was designed, the Confederation Life Building included a 214-foot tower (now truncated), rounded corner turrets, and pinnacles on the gables. The interior featured fanciful finishes such as marble, mosaic tile, and white oak. Modern amenities such as electricity, elevators, and large windows served the workers inside. The top floor also included an assembly hall, dining room, and lounge.

In 1899, early alterations removed parts of the stone base and vaulting in favor of ground-floor storefronts with carved stone borders. These were designed by James Wilson Gray. The ornamentation is intact today, but the windows have been replaced.

1950s photo of the building, after its alterations. (TorontoJourney416)

Confederation Life moved out in 1955, and the building was sold. The pinnacles and tower peaks were removed around this time. It was popular with lawyers and accountants. It was designated a heritage building in 1975. During a renovation in 1981, hot tar used on the roof started a fire that caused major damage. Engineers deemed the structure to be stable enough for repair, and it was then restored.

I kinda short circuited again trying to get wider photos of this one. I guess I need to practice my photos in more urban fabrics.

Yonge Street facade:

The pointed hood molds over the windows indicate Gothic Revival influence. I like the iron window framing too.

Detail of the copper roof:

Romanesque vault with iron bay window:

Truncated central tower on the Richmond Street facade:

This arch at the base is pointed:

However, this next one has a more typical Romanesque round vault and naturalistic ornament:

Note the dragons in the spandrels. Pretty cool.

Dineen Building

Historic photo of the Dineen Building. (Commercial Realty Group)

The Dineen Building is a Renaissance Revival office building that was originally built for W. & D. Dineen Co. Hats. It was completed in 1897 by architect Frederick Henry Herbert. The interior once featured aluminum plate ceilings and a Sprague automatic elevator, both firsts in Canada. In 1917, an electrical fire severely damaged the building, though it was repaired.

The Dineen Building in poor repair c. 2010s. (Commercial Realty Group)

The Dineen Building was listed as a heritage property in 1973. Over the years, the cornice was removed, and the storefronts were renovated, leading to it being in poor condition by the 2010s. In 2012, an extensive renovation restored the sooty exterior and recreated the lost cornice and storefronts, which also added the glassy volume on top.

It’s neat that the tenants are named after the original owners, and this building has been very excellently restored. If only other developers could follow this model.

To be fair, it helps that a lot of the details were left in situ and simply needed restoration.

Elgin Block

Historic photo of the original appearance of the Elgin Block. (Globe and Mail)

Although this building’s current form dates to 1910, it has essentially been mirrored across the midpoint of this block as part of the Bay Adelaide Center. The Elgin Block was built as an early Italianate design in 1850, ostensibly stretching from Temperance Street to Adelaide Street along Queen Street. In 1901, the building was altered for Ryrie Brothers and Matthew Sheard, and in 1910 it was modified again into the Commercial style for the department store Holt Renfrew, which operated there until the 1950s.

The Elgin Block after its Commercial style alterations. (ERA Architects)

By the 2010s, the Elgin Block was in shoddy repair. It was missing its cornice, needing to be cleaned, and its original storefronts had been lost. As part of the Bay Adelaide Center project, built between 2007 and 2022, the east and south facades were removed from the building, which was then demolished for the construction of the towers’ podium. They were then relocated to the northeast corner of the site, where the south facade then became the current north facade. Additionally, the storefronts and cornice were restored.

Like me, you might have immediately noticed the three bays on the left that appear to have been painted an abysmal shade of beige. Interestingly, this was ERA Architects’ solution to needing larger floor plates than the original building had--it is actually a concrete cast of the facade, what the firm describes as a “ghost wall.” They disassembled the facade into pieces, which were used to make molds that ultimately formed the concrete.

ERA justifies this decision as “... not to fool the eye, but…to suggest the missing fabric of the Elgin Block, opening a conversation about our local history of urban development, and about the overall discourse of heritage interpretation.” Looking closer, I can see that it is actually concrete now and not some landlord-special “modernization.”

Upper Canada Bible Societies & Tract Building

This Second Empire building was constructed by Gordon & Helliwell in 1886. The original tenant published Bibles in different languages for incoming immigrants, and later occupants were clothing and drug stores. Its storefront has since been altered.

Robert Fairweather Building

A 1919 Beaux-Arts design by architect Charles S. Cobb, this one is very intact and appears to retain its original windows or careful reproductions.

Commercial Travellers Association Building

Though this building dates to 1847 (probably an Italianate originally), it has been modified multiple times in the late 19th century. It was designed by John G. Howard for A. V. Brown. Its facade was altered between 1872 and 1881 for Casimir Gzowski, and the Second Empire mansard roof dates to before 1890 and may have been added at the same time. In 1890, the building was modified further for the Commercial Travellers Association, granting its best-known name. As it stands today, it is a well-preserved Second Empire design with elaborate pilasters and keystones.

Bank of British North America

This Second Empire bank reminds me of the ones that dot Old Montreal. It was completed in 1873 using Ohio sandstone by architect Henry Langley, replacing an older building on the site used by the same bank. The building was renovated in 1903 by Burke & Horwood, who maintained many of the original features.

The Bank of British North America and Commercial Travellers Association Building are planned to be merged into a larger 62-story skyscraper.

Brookfield Place Historic Buildings

These next several buildings have been incorporated into the base of Brookfield Place. They aren’t heritage buildings, and I wasn’t really able to find much after a cursory Google search, so I’ll just dump them all unceremoniously here.

A quite modern-looking Beaux-Arts design on the corner, the only anachronistic details being the spandrels and pedimented windows: