History by the Park:

Exploring Heritage in Toronto's High Park North Neighbourhood



Language: English 

Area: Downtown

Theme: Arts & Architecture; History & Culture


By Christina Ransom

Information Specialist, Access Copyright

Walk Description:

Embark on a self-guided walking tour of the High Park North neighbourhood and learn the stories of early residents of the area, including the first mayor of the Village of West Toronto Junction, a portrait painter, and a naturopathic doctor who believed in the healing properties of an Olympic-sized swimming pool. We will examine how popular urban planning philosophies such as the City Beautiful Movement, Towers in the Park, and facadism have played out in and shaped this neighbourhood.


Stop 1: Carleton Race Track

Address: Corner of Humberside and High Park Avenue


If you had been standing in this spot back on June 27, 1860, you could have had a prime view of the first-ever Queen’s Plate. Before it became part of the Junction and High Park North neighbourhoods, this area used to be home to the Carleton Race Track, built by farmer and businessman William Conway Keele on his estate. The racetrack was an oval, and High Park Avenue and nearby Pacific Avenue to the east would have been the sites of the straightaways, reaching from Glenlake Avenue north to Annette Street. Standing where you are now, you would have been in the centre of the stands on the western side of the track.

The Queen’s Plate was held here for 4 years until 1864, and was then held at changing venues until 1892, when its permanent home became Woodbine Racetrack. It is estimated that between 2000-4000 people came to this site to be spectators at the first Queen’s Plate in 1860. Eight horses were entered in this original race, and 5-year-old Don Juan took home the 50-guinea prize awarded by Queen Victoria.

Walk Route #1: Begin at intersection of Humberside and High Park Avenue, on the northeast corner.

Present Day Intersection of High Park Avenue and Humberside Avenue.

Carleton Race Track in the 1870s.


Stop 2:  The James T. Jackson House

Address: 204 High Park Avenue


In the late 1800s, High Park Avenue featured grand homes built for some of the wealthiest families living in the Junction. Following the closure of the Carlton race track, Daniel Webster Clendenan, a young lawyer from Jordan, Ontario (in the Niagara region) purchased the land and subdivided it into plots for homes and businesses. Clendenan knew the railway would soon pass through the area, and rightly predicted that an increased demand for goods and services and housing stock would follow. Dundas Street became the commercial heart of the community (Bloor Street was still underdeveloped at this time), and High Park Avenue became the residential core. Customers looking to buy land and build houses had to take the train from Union Station, as the horse-drawn streetcars only went as far as Lansdowne at the time. Dundas Street West was temporarily home to upwards of 26 real estate offices between Quebec Avenue and Willoughby Avenue.


This house was home to James T. Jackson, a real estate agent who founded the Junction’s first newspaper in 1888, The Daily Tribune. The house was built in a grand style to reflect James’ success in his profession. For example, the exterior of the house features sandstone, a more expensive material than brick. The interior features wood paneling and an inter-connecting parlour and dining room for large parties and social gatherings.


At the time, the Junction neighbourhood was actually part of the Village of West Toronto Junction, established in 1888 and amalgamated with the City of Toronto in 1909.


Today, 204 High Park is occupied by the Holy Cross Priory, an Anglican monastery.

Walk Route #2: Cross the street to the northwest corner to view 204 High Park Avenue.

204 High Park Avenue


Stop 3: The D. W. Clendenan House

Address: 191 High Park Avenue


This house is the home of Daniel Clendenan. Both this house and 204 High Park were designed by James Ellis, a prominent Junction architect. Clendenan may have been the reason that Ellis became so active in the Junction area, as Clendenan and Ellis attended the Disciples of Christ Church together.

Clendenan was elected deputy Reeve of York township in 1885, and worked to get the Village of West Toronto Junction incorporated, eventually serving as mayor. Clendenan initially brought economic prosperity to the Junction when he convinced the CPR to move its railway shops here from Parkdale, with an offer of free water and reduced taxes. Unfortunately, the Village incurred significant debt from this deal and eventually this led to its amalgamation with the city of Toronto.

This house, with its octagonal shape and wide country windows, has a cottage-y feel to it that would not have been out of place when it was one of the only houses on the street in a relatively rural area.

Walk Route #3: Cross back to the northeast corner, walk south on High Park Avenue to 191 High Park Avenue.

191 High Park Avenue

166 High Park Avenue


Stop 4: The Heintzman House

Address: 166 High Park Avenue


This house was built in 1891 for Herman Heintzman, the eldest son of Theodore Heintzman, founder of Heintzman and Company, a piano manufacturer, and one of the most prominent businesses in the early years of the Junction neighbourhood. The house features eclectic Victorian architecture that was typical of the time period. The windows feature stained and etched glass, and the smallest of the windows in the circular staircase of the tower feature musical motifs.

Why does this house have a tower? Likely included to add architectural variety, towers were a common feature of upper-middle class homes in this time period. Other explanations include the fact that there was a ravine at Keele Street at the time that led down to Grenadier Pond and Lake Ontario that might have been visible from the tower. It’s also possible that the tower afforded a view of the Heintzman factory over to the northeast, as it was one of the tallest structures in the Junction at that time.

High Park Avenue is a good example of the City Beautiful movement, an urban planning philosophy that was popular in Canada from the 1890s until the 1930s. The City Beautiful movement promoted planned and purposeful creation of civic beauty through architectural harmony, unified design, and visual variety. Tree-lined boulevards such as this one were a key component of the movement. Although the City Beautiful movement appeared to focus on aesthetic qualities, a planned city also meant a humane and livable city (and the experience of beauty and of living in beautiful surroundings was believed to contribute to an individual’s physical and mental well-being). This was seen as a contrast to the American cities of the time period, which had shot up quickly in response to unprecedented population growth, and therefore lacked planning or purposeful construction. The City Beautiful movement is the precursor to the detailed urban planning departments we have in modern times.

Walk Route #4: Continue south on High Park Avenue to 166 High Park Avenue – house is on western side of the street.


Stop 5: Tower in the Park Movement

Address: Corner of High Park and Glenlake


As you stroll down High Park Avenue today, you will see a marked shift as you get closer to Bloor Street. Up until now, you will have been walking past century-old homes in the Victorian, Edwardian and Tudorian styles. As you journey further south, you will find that apartment buildings now dominate the landscape. This is the result of the “blockbusting” of the 1960s, wherein single homes of the sort you have been walking past were torn down to make way for residential towers and complexes. This was a natural site for this type of blockbusting, as the Bloor Street subway had just arrived one block over at Keele Street in 1966.


The apartment buildings that resulted from this blockbusting are an excellent example of the Tower in the Park architectural style that was popular in North America in the 1960s and ‘70s. The idea of Tower in the Park is as follows: taller towers allow for more green space to exist between buildings without sacrificing density. Therefore, residents enjoy the benefits that access to green space, light, and air provide, while still living in dense communities. You will notice that the towers in this apartment complex are set perpendicular to each other – this allows for more light and also ensures that residents are not directly looking into the homes of their tower neighbours. Although no longer in use, many of these buildings were initially built with fountain courtyards in front.


Builders were heavily incentivized to build Towers in the Park during these decades – the Canadian Mortgage and Housing Corporation (CMHC) rewarded developers who created higher density projects, and also those who had a higher percentage of green space on their lots. It is estimated that one tower was built for every 2 single family homes during this time period. The overall goal at the time was to curb urban sprawl and preserve the rural lands lying at the edges of large municipalities.


There are, of course, some drawbacks to the Tower in the Park model. Because the model encourages builders to construct towers surrounded by green space, these communities can become less walkable than flatter, mixed-use communities. In other words, residents must travel farther on foot and cover more distance to reach grocery stores, libraries and other community amenities. City planners have tried to counteract this obstacle in more recent times by ensuring the ground level of new condominiums are occupied by retail space.


This model also violates Jane Jacobs’ principle of “eyes on the street”. Jane believed that shorter towers are more beneficial than taller towers because residents are more apt to “watch” the street and therefore be aware if a crime or other danger is taking place. As a result, the community feels safer. Creating mixed-use neighbourhoods (i.e. where housing and commercial buildings co-exist) also contributes to this goal by ensuring that there will be people on the street at all hours of the day (in contrast, neighbourhoods that are made up only of commercial buildings may be deserted after 5 pm, and neighbourhoods that are solely residential may be relatively empty during the day). By essentially putting residents on an island in the middle of a green space, Towers in the Park do not contribute to a mixed-use concept.


Some architectural historians in Canada have lobbied for the preservation of these Towers in the Park, as they represent a distinct era of Canadian architecture.

Walk Route #5: Continue south on High Park Avenue to intersection with Glenlake Avenue.

The Towers in the park north of Bloor Street that resulted from the 1960s era blockbusting in the neighbourhood.

Another example of Towers in the Park in North York.

Present day exterior of 70 High Park.

Interior lobby of 70 High Park – preserved from 1928.


Stop 6: The Third Church of Christ, Scientist

Address: 70 High Park Avenue


The 21-storey condominium on the site of 70 High Park Avenue was built in 2003. However, the façade offers clues as to the original purpose of this site. Back in 1928, architect Murray Brown built the Third Church of Christ, Scientist here. Brown is celebrated for creating buildings that combine a Modern Classic exterior with Art Deco interiors. Brown is also the architect behind The Regent Theatre on Mount Pleasant Road and the Long Branch Public Library. The church closed in 1999, and the site remained vacant until it was purchased by the development company.

The original façade of the church was preserved and incorporated into the design when the site was bought by a developer for the purpose of building the present-day condo. The original lobby, with its plasterwork and terrazzo floors has also been preserved. The site was designated a heritage property by the City of Toronto in 2008, meaning that any future alterations or rebuilds on the site must also preserve the original church building to the greatest extent possible.

However, the building is not without controversy. Some critics argue that the result of preserving and incorporating the façade of the church has resulted in a building worthy of architectural ridicule. Dave Leblanc writes in the Globe and Mail that the original façade looks “bullied, small and sad”, dwarfed as it is by the new building’s massive columns, typical of the podium-style condos that have been so popular in the first two decades of Toronto architecture. Leblanc argues that the developer shouldn’t have bothered if he wasn’t willing to push the new structure further back from the street, thereby giving the façade of the original church more prominence.

The condo draws to mind larger debates about façadism in Toronto, which has taken on many forms. Some redevelopments of heritage buildings preserve only the façades themselves (i.e. only the exterior of the original building), whereas others, like this one, preserve the façade alongside at least some original interior elements (in this case, the lobby). Other redesigns preserve the entire building, such as the old mansions on St. George Street that have been repurposed into University of Toronto buildings.

Proponents of facadism argue that it offers developers, city planners and heritage advocates an invaluable balance – the ability to preserve the character of old buildings and the urban streetscape while still increasing density to meet the growing needs of the city. Opponents argue that the result can sometimes be disorienting and garish, with neither the old or the new building appearing comfortable in the space or aesthetically pleasing. The argument often speaks to a deeper mismatch in beliefs between individuals who believe that the outside of the building, the part that plays a role in the public realm, is most important, and others who argue that a big part of the beauty of heritage buildings is observing how small buildings work together in a neighbourhood.

Walk Route #6: Continue south on High Park Avenue to 70 High Park Avenue.


Stop 7: The High Park Mineral Baths

Address: 32 Gothic Avenue


This house was built in 1889 for George Johnston St. Leger, the second mayor of the Junction. George worked in the retail shoe business and served on Toronto city council before retiring to the Junction and becoming mayor in his 60s.

George named his house Clandeboye, after a prominent estate in his native Ireland. The site of Clandeboye included a carriage house, a stable, and a driveway that featured a large arch reading “Cead Mille Falthe” the old Irish for ‘A Hundred Thousand Welcomes’. George lived at Clandeboye as his primary residence during his time as mayor, but later rented it out before finally selling the property.

The house has had multiple other owners since George’s time. In 1907, William James McCormick bought the house and turned it into the High Park Mineral Sanitarium, where he treated diseases of the nervous system. William’s treatment philosophy was in line with that of American John Harvey Kellogg (of cereal fame), who ran a similar facility in Battle Creek and believed that being in and surrounded by nature helped to prevent and cure disease. At the time, Grenadier Pond and Lake Ontario would have been visible from the site’s vantage point high atop the hill, and it was consequently seen as the perfect tranquil setting for such treatment.

William enlarged the on-site swimming pool until it was the size of an Olympic pool – at the time, it was the only Olympic-sized pool in the city – and also had an addition added onto the house. Despite the addition, tents were often pitched on the site to accommodate overflows of patients (the house had a maximum capacity of about 20).

The swimming pool became a popular attraction with locals in the area. The pool was open to the public from 9 am to 9 pm in the summer months, and the McCormicks hired swim instructors to provide lessons to the public at no extra charge. The pool hosted Olympic swimming and diving trials in 1924.

William closed the sanitarium in the early 1920s, following the death of his wife and later his son, who drowned while playing near the pool. In the 1940s and ‘50s, William rented out 32 Gothic as a maternity hospital (Strathcona Hospital), and continued to operate a private practice from his home at 16 Gothic Avenue.

William opted to keep the mineral baths open, motivated by his steadfast belief in the health benefits of outdoor activity. The baths remained open until the early 1960s, when the land in the area was resculpted to accommodate the arrival of the Bloor subway.


Most recently, in 2007, the house was converted into 8 condominium units.

Walk Route #7: Continue south on High Park Avenue to Bloor St. Turn right (west) onto Bloor Street. Continue to Quebec Ave. Turn right (north) on Quebec Avenue. Turn left (west) on Gothic Avenue and walk to 20 Gothic Avenue.

Present day 32 Gothic Avenue.

32 Gothic Avenue when the Mineral Baths were open.

Present day.


Stop 8: The C. M. Hall House

Address: 245 Glendonwynne (originally 320 Quebec Avenue)


This house was designed by James Ellis for Charles M. Hall, a portrait painter who painted the portraits of Junction mayors James Bond and G. W Clendenan (cousin of D. W. Clendenan). Construction began on the house in 1905. The original address of the house was 320 Quebec Avenue.

The house was the only one on the street for the first 7 years of its existence, and this is obvious from its unusual orientation. The front of the house faces northwest, away from Quebec Avenue, suggesting that the original land plot was of a large size, and therefore the house could be placed without regard for its orientation to the street. Archival photos suggest that the front lawn was originally much larger, and that the creation of Glendonwynne Road may have reduced the property size significantly.

The house is Georgian in style, and also features influences from the grand colonial-style homes that were popular in Toronto in the 18th and 19th centuries. Inside, the front door opens onto a central hall and staircase.

Walk Route #8: Walk north on Quebec Avenue until you get to the intersection of Quebec Avenue and Glendonwynne Road. You will see tennis courts in front of you. To the right, Quebec Avenue continues north, to the left, Glendonwynne Road goes southwest. You will need to turn left onto Glendonwynne and follow it until you reach 245 Glendonwynne.

245 Glendonwynne Road (then 320 Quebec) showing larger lawn.


Stop 9: Humberside Collegiate Institute

Address: 280 Quebec Avenue


Originally opened in 1892, Humberside Collegiate Institute began its life as Toronto Junction High School in the basement of the Victoria Presbyterian church on Pacific Avenue (now the site of St. Cecilia’s Catholic Church). It moved here to the current site in 1894 to accommodate a growing population, and was renamed Humberside Collegiate Institute when the Junction was annexed by the City of Toronto in 1909. The original school featured only 5 classrooms.

The front entrance of the school is a memorial to the students who lost their lives in World War I. Additional names were added after World War II. The memorial includes striking stained glass windows. Another notable piece of art in the building is a mural painted by Arthur Lismer (a member of the Group of Seven) in the 1920s, housed in the auditorium (which has been renamed Lismer Hall). This is believed to be the largest mural ever painted by Lismer. The mural depicts a scene featuring a gathering of soldiers and Indigenous peoples. The Indigenous women are modelled on Gauguin’s famous Tahitian women. Major renovations in the 1920s and 1960s added new wings to the school. The mural was partially damaged and lost during the renovations of the 1960s, but has since been restored with help from conservators from Queen’s University.

There are a number of flowering trees lining the paths that crisscross the schoolyard – these were planted to commemorate the City of Toronto’s sesquicentennial in 1984.

1992 marked Humberside Collegiate’s centennial anniversary. The occasion was marked by the installation of additional stained glass windows by Canadian glass artist Robert Jekyll. The windows feature scenes from Canadian history, and were designed with the help of research compiled by grade 10 students (the stained glass initiative was spearheaded by history teacher Mel Greif).

The school remains an excellent example of collegial Romanesque architecture of the late 1800s and early to mid-1900s.

Walk Route #9: Walk north on Glendonwynne back to the intersection of Glendonwynne and Quebec. This time, continue past the tennis courts and follow Quebec Avenue as it continues north. You will see a driveway leading up to Humberside Collegiate on your left (the intersection with Humberside Avenue will be on your right).

Present day exterior.

Examples of stained glass throughout the school.

The mural painted by Arthur Lismer.

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