Nothing specific this post – just a desultory early Spring photowalk through parts of downtown Toronto:
Category: Neighbourhood photowalks (Page 1 of 5)
I’ve always loved walking down the short stretch of Glen Road from Howard Street to the Glen Road footbridge. To me it has always exuded a quasi New York feeling with its walk-up apartment buildings and Victorian houses, capped off by “Howard Village” at the south end of Glen Road:
Things here, though, weren’t always so pretty. Years ago, this stretch of Glen Road was an abandoned, decayed mess, as these shots from the 1980s demonstrate:
I remember walking down this decayed part of Glen Road many years ago, when it was at its worst, and thinking how great it would look if the whole street were restored. Well, that did actually happen – from 2005 to 2016 this section of Glen Road was restored, and now is quite beautiful.
I knew that Glen Road continued on to Rosedale the other side of the footbridge, but I didn’t know how far north of there the street actually extended. I set out to shoot Glen Road, thinking it was a small street and wouldn’t take much time to cover. As I followed it I discovered it just kept going and going, twisting and turning through Rosedale, onward north well past Summerhill Avenue, then finally ending where it encounters the Don Valley Brickworks Park. The length of this street amazed me… who knew?
I started my photowalk on the south end of Glen Road, where it begins at Howard Street. Howard Street, by the way, is currently undergoing a massive condo boom and some much-needed gentrification, but that’s another post for another day.
Number 1 and 7 Glen Road
Number 1 and number 7 Glen Road are known historically as The Roslyn Apartments. They were built in two phases, with 1 Glen Road completed in 1912 and 7 Glen Road completed in 1911. The apartment buildings were designed by architect J.A. Harvey.
These two buildings complement each other but are not identical in design. Featuring red brick cladding with brick, stone and wood detailing, both buildings are three stories in height above raised bases with window openings. The rooflines are marked with extended eaves and parapets.
Number 6 and 8 Glen Road
These Glen Road houses were in place by September 1884 according to the tax assessment rolls. The occupants in 1885 included merchants, an estate agent, and the owner of a livery stable. The properties were listed on the City of Toronto Inventory of Heritage Properties in 1974, along with the other remaining buildings along this short stretch of Glen Road:
Number 10 and 12 Glen Road
These two Glen Road Houses were also in place by September 1884. The Glen Road buildings in this stretch are examples of late 19th century houses with patterned brickwork. This style of house was once prominent on Sherbourne Street and in the adjoining neighbourhood:
The Sherbourne Subway Entrance & Glen Road Pedestrian Tunnel
Here are some shots I took of the footbridge area in 2021. I much prefer the current version!:
Current Rejuvenated Tunnel and Footbridge
In The Tunnel
Inuit artist Couzyn Van Heuvelen designed the birds and animals in the Glen Road Tunnel. The project is centred around the theme of migration and travel, and references Inuit stonecut printmaking techniques and stone carving:
The New Glen Road Pedestrian Bridge
The City of Toronto has replaced the Glen Road Pedestrian Bridge (aka the Morley Callaghan Footbridge) across the Rosedale Valley Ravine. The new bridge debuted on May 30, 2025.
The design retains the core visual character of the original bridge while enhancing the above-deck user experience and safety with innovative V-shaped barriers, stainless steel webnet, and LED lighting. The bridge and tunnel have been widened to increase openness and sightlines:
Rosedale… How the Other Half Live
It was fascinating just wandering up Glen Road, observing the elaborate houses and mansions. There’s a little piece of history in so many of the houses there:
Built in 1902, designed by Architect Frederick H. Herbert
This house was built in 1903. It was the home of Ambrose Small, the hated and envied owner of theatres across the province. He disappeared in 1919 along with $10-million from his bank account. He has never been found.
Built in 1901 in the style of Second Classical Revival, with a full-height Ionic-columned entry porch.
Constructed in 1911, designed by the Designing and Drafting Company consisting of D.C. Cotton and H.G. Macklin. The house is a neat, symmetrical red-brick neo-Georgian with Craftsman porch, eaves, and dormers.
Second Classical Revival houses with full-height Mount Vernon porches were very popular during the first half of the 20th century. This house was built in 1901 by the architects Chadwick & Beckett. This beauty is currently up for sale with Harvey Kalles Real Estate Ltd. for a paltry $8,900,000.00.
105 Glen Road – “Ravine House”
Built in 2002 by architects Kuwabara Payne McKenna Blumberg. One of the few houses in Rosedale to show modernity on its face as well as its landscaping. The house is surrounded by the fence’s dark teak slats, broad-brush expanses of groundcover, and grass facing Glen Road.
Built in 1920, designed by Architect William B. Galbraith. The house was reconstructed in 2006.
Built in 1932
This house was constructed in 1909 in the Tudor Revival style. It is a 6 bedroom, 7 bathroom house with 4 parking spots on a 68 x 109.17 foot lot. The house recently sold for $5,580,000.00.
Known as the Charles Davies House. This stone-veneered house was built in 1910 to plans by Curry and Spalding, architects for Charles Davies. With its novel rounded tower, it manages to look modern yet traditional, taking cues from the English Cottage style.
Known as the Burton House, built in 1928 and rendered by architect Douglas Kertland in the English Cottage style. Its rambling nature suggests a crofter’s cottage from Shakespeare’s day, especially with its regular arrangement of gables and windows, the mix of building materials, the steep roof and the plethora of primitive-style detailing inspired by medieval times.
159 Roxborough Drive, corner of Glen Road. Rosedale United Church opened in 1914 as Northern Congregational Church. The building was completed in 1913 in the Gothic Revival style by architect John Gemmell. In 1925, when the Congregational Church merged with the Methodist Church of Canada and two-thirds of the Presbyterian Church in Canada to form the United Church of Canada, the church was renamed Rosedale United Church. In 2014, singer Gordon Lightfoot was married to Kim Hasse, his third wife, in the church.
This is a Heritage property, built in 1913
This owner has installed a bollard behind the SUV in their driveway
Text references:
The Glen Road Village
City of Toronto, Glen Road Pedestrian Bridge & Tunnel Replacement
A Brief History of Glen Road Village
City of Toronto, Heritage Preservation Services, William Muir Houses
The Water’s Edge Promenade stretches from Sugar Beach near the foot of Jarvis Street, past Sherbourne Common, ending at the foot of Parliament Street – for now. There are future plans to keep extending Water’s Edge Promenade further along the eastern waterfront.
The Water’s Edge Promenade was a Waterfront Toronto initiative, envisioned by West 8 (an award-winning international office for urban design and landscape architecture) and DTAH (a landscape architecture and urban design company) as the “Green Foot” of the city at the edge of Lake Ontario.
Silva cells provide adequate soil volume for healthy tree growth of the double row of fall colouring maple cultivars, and rainwater is captured to water the trees as a passive irrigation system. The trees were selected a year ahead of planting, and were hand-picked individually at various local nurseries, as a cautionary measure due to the high profile nature of the project, and the significant quantity of trees required for the area (including for the adjacent Sugar Beach).
The granite cobblestone “maple leaf” promenade was constructed with skilled Irish stonemasons who were brought over to teach local contractors this special technique. The project is also part of the East Bayfront District’s comprehensive stormwater management plan, which includes a future wood boardwalk over a forebay system to treat stormwater runoff as part of the ‘treatment train’ approach employed.1
Condos… lots of ’em
Almost as noticeable as Lake Ontario are the condo developments on, and near, the Water’s Edge Promenade:
I must say that the most striking building I observed on this walk was the Aqualuna Condos, located at 155 Merchants’ Wharf. This building was absolutely stunning and I was fascinated by its colour, form and architecture. Its opulent design was created by Danish architects 3XN, and apparently the building features first class amenities. I shudder to think what a unit here would cost.
The Water’s Edge Promenade is considered one of Canada’s Best Landscape Architecture Projects. It’s so nice to see our long-neglected waterfront coming to life and becoming a welcoming destination within the city.
As most know, the Toronto Islands are comprised of three small land masses – Hanlan’s Point, Centre Island and Ward’s Island – joined in an arc.
Ward’s Island is on the east side of the Islands. Unlike Hanlan’s Point and Centre Island, which are full of picnic areas and BBQ sites, Ward’s is mostly residential, having a quiet, calm aura to it.
Exploring The Cottages
On Ward’s Island there are 262 homes and roughly 650 people living on the Island. The community has no stores, cars or public transportation, so life is very different for Islanders:
Think you want to live on Ward’s Island?
Well think again… it’s an awful long wait. There is Legislation in place for Island residents which safeguards their homes: The Toronto Islands Residential Community Stewardship Act. Under the Act, the deed to a house may be transferred only to the current owner’s child or spouse. If the house must be sold for personal reasons, and if a child or spouse will not be the new owner, the process is handled by the Toronto Islands Residential Community Trust Corporation. The house and the land lease are sold for the owner’s benefit, but the buyer must be an individual on a 500-person waiting list which was established through a lottery. A firm price is set by the Trust; no bids or negotiation are allowed. This process was intended to eliminate the risk of the homes being sold on the open market, driving up the prices, and preventing a windfall for the owner.
Down to the Beach
The Ward’s Island beach is located at the start of the boardwalk, next to a small playground and washrooms behind the soccer field. It’s the least busy of the three main beaches of the Island.
An old-fashioned boardwalk runs the length of the southern shore, starting at Ward’s Island Beach and passing the back gate of Riviera cafe with its lovely patio.
“The Anatomy of Fear” by Bruce Smith
On the north part of the island there is an interesting art instalment by artist Bruce Smith, who lives on Ward’s Island. The instalment is described by the artist:
Fear can give rise to frantic despair and also can lead to progression. This duality is represented in “The Anatomy of Fear” as the right and left wings. The terrifying right wing consists of the body of the dragon, filled with “Big Bucks” ($): a bat wing coloured red to indicate hysteria and disruption. A contemporary analogy of this wing is the denial of global warming and refusal to engage in carbon emission reduction programs. The benign left wing is filled with common sense “c”, coloured environmentally-friendly green with shape derived from a dove.
Back to the Mainland…
Watching a suggested video on YouTube a few days ago reminded me of a fascinating urban relic in Toronto: the Hearn Generating Station:
The Hearn Generating Station (named after Richard Lankaster Hearn) is a vast decommissioned electrical generating station down in the docklands. The plant was originally fired by coal, but later converted to burn natural gas. Everything about the plant is on a massive scale and, according to sources, encompasses 650 thousand cubic metres of space. The plant opened in 1951 and closed in 1983.
The R. L. Hearn Generating Station was the site of Canada’s first 100 MW steam turbo-generator set. The station sits in what was once Ashbridge’s Bay, a shallow marsh that was filled in with rubble from downtown construction sites from 1911 to 1950s.
Located in the Toronto Docklands, the Hearn’s surrounding area has not been gentrified whatsoever. You would not know you are still within the boundaries of the City of Toronto; the location feels remote and desolate:
The Hearn Generating Station is located at 440 Unwin Avenue. Once reachable only by car or on foot, a TTC bus now has a route down Cherry Street which will take you to Unwin Avenue after passing over two of the dockland shipping channels. There are no sidewalks down Unwin Avenue, and it’s a long and dusty trek past industrial warehouses and landfill mess to get out to the Hearn.
Not the most uplifting neighbourhood…
Approaching the Hearn
At any rate, my goal is now in sight:
The architecture and former use of the structure of the Hearn reminds of the Battersea Power Station in London, UK. The Battersea, though, has been restored and transformed into a very hip and modern venue with a mixture of over 150 shops, bars, restaurants, leisure and entertainment venues. The Battersea has thrived but the Hearn currently remains decayed and abandoned.
BlogTO recently called the Hearn Generating Station the most dangerous site in the City of Toronto… with good reason. The site is a favourite with urban explorers and photographers, and there has been more than one death of these intrepid people on the site:
I was able to get these shots by sticking my camera lens through the fence (security is quite serious here, and the rolled barbed wire at the top proves a point). I was being closely watched by the Security there, but had no nefarious or illegal intent other than grabbing a few shots for the blog:
Here is the excellent YouTube video which triggered my interest in the Hearn Generating Station:
A Rebirth… Sort of
On June 5, 2014, the building was partially cleaned up and used for the Toronto Luminato Festival Big Bang Bash, their 2nd annual fundraising gala. It also featured the Yves Saint Laurent Opening Night Party later that evening. In 2015 the building was used for UNSOUND hosted by Luminato Festival. In 2016 Luminato Festival used the building for its festival.
There is Hope for its Future, Though…
There are future plans, though, for this behemoth and the portlands area in general. According to the development site:
A massive redevelopment proposal is planned for the historic Richard L. Hearn Generating Station in Toronto’s Port Lands. Dubbed The Hearn District, the redevelopment would incorporate the shuttered power station into a multi-use district to be built over 30 acres by the Cortel Group. With the conceptual design for the masterplan by PARTISANS, SvN, and public realm design by CCxA, the proposal envisions thousands of residential units and extensive cultural and commercial spaces.
Click here to read the full details of this redevelopment proposal.
Let’s hope this comes to pass. It would be wonderful to see this amazing building and the desolate area of Toronto come alive.
The sun was actually shining for more than three minutes last weekend, so I set out for another photowalk in the city. It had been a few years since I’d walked along Richmond Street East, so I thought I’d give that street a try with my trusty camera in tow.
Richmond Street East runs from Yonge Street to just east of Parliament Street, where it crosses the Don River and becomes known as Eastern Avenue. As you walk along Richmond Street East, you can tell its had a long history of hard labour and warehouses. In the 20th century, the area saw the rise of large-scale warehouses, factories, and office buildings, many of which replaced earlier low-rise structures.
These days Richmond Street East is definitely – and literally – on the rise: there are condo projects everywhere you look. The street is a vibrant part of Toronto’s downtown core, with a mix of commercial, residential, and entertainment spaces.
Walking from the start of the street at Yonge, and finishing at Parliament, here’s a bit of what I encountered:
blogTO calls the Chester Hill Lookout “Toronto’s secret observation deck” and, after visiting the location, I would have to agree with them.
Sitting at the end of a quiet residential road off Broadview Avenue, the Lookout is a semi-circular concrete observation deck jutting out at the end of a cul-de-sac on Chester Hill Road:
The Lookout offers a view that spans west across the city, with the Don Valley and the whizzing of cars on the highway below, Evergreen Brick Works sit beyond the trees to the right and the towering financial buildings to the left.
Finding the Lookout
From the Danforth, walking a few minutes north on Broadview Avenue will bring you to Chester Hill Road:
Chester Hill Road is a very quiet, upscale neighbourhood with some beautiful homes:
At the end of the block you will encounter a cul-de-sac:
Painted on the pavement of the roundabout is an astrology wheel. This chalk-work is by local artist Victor Fraser, a sidewalk artist and poet based in Toronto. He has been painting paved surfaces for the past 20 years, and has painted in six different countries. The wheel was repainted in October 2022.
Stepping to the edge of the roundabout yields an incredible urban view:
The Chester Hill Lookout was built in the late 1950’s for the construction of the Don Valley Parkway. Chester Hill Road was shortened to create the Lookout and the hillside down to the DVP. The land over the edge of the Lookout down to the DVP is owned by the Toronto Regional Conservation Authority, but leased by the City of Toronto.
Residents of Chester Hill Road report a downside to the location, though. There have been many negative issues occurring lately including speeding, drug use and dealing, impaired driving, garbage, vandalism, late night noise/partying and parking violations.
On a happier note, while the Lookout is beautiful at any time of the day, sunset and nighttime offer the most spectacular experiences. As the sun sets, the sky takes on hues of orange and purple with the city’s lights twinkling below. At night, the Luminous Veil of the Prince Edward Viaduct adds a purple touch to the view. I’m planning a revisit to the site next spring to capture some of this.
A few days after Halloween I took a walk through Cabbagetown on a beautiful, crisp fall day. The houses and streets were a weird and eclectic mix of post-Halloween gore, front yard kitsch, Autumn colours and falling leaves:
Wellesley Avenue
Wellesley Avenue
Wellesley Avenue
Wellesley Park
Wellesley Park
Kitty trapped on rooftop
On the northeast corner of Parliament and Carlton Streets
Mural on southeast corner of Parliament and Carlton Streets
I took a little walk around the York Street-Bremner Blvd. area one sunny Sunday last month, randomly shooting the city as it went about its business. I had to curtail my walk, though, as there were masses of people heading to the Rogers Centre for a Blue Jays game and things were getting more than a little crowded. Regardless, I grabbed a few random shots before leaving the area.
This guy was having a great time with his karaoke machine, serenading pedestrians from atop the underground parking stairway at the intersection of York Street and University Avenue. I guess I’d call this “elevated busking”:
This retired old Dodge police car went thundering past me on Front Street West:
Reflections while walking along Bremner Blvd.:
Looking up, Maple Leaf Square, behind the Scotiabank Arena:
For some time I’d known this sculpture was just behind the Scotiabank Arena, but not being a hockey fan, I couldn’t have cared less. I did find out, though, that the piece is entitled Legends Row, created by Erik Blome from 2013 to 2017:
At 110% the size of their likeness, the “Legends Row” sculpture is truly larger than life. The sculpture depicts 14 of Toronto’s greatest hockey legends outside the current home of the Toronto Maple Leafs, the Scotiabank Arena (formerly the Air Canada Centre). Commissioned by the Toronto Maple Leafs Hockey Club. There are fourteen figures in total including: Wendel Clark, Turk Broda, Charlie Conacher, Syl Apps, Darryl Sittler, Johnny Bower, Mats Sundin, Borje Salming, Teeder Kennedy, Dave Keon, Tim Horton, Frank Mahovlich, Red Kelly, and George Armstrong. With the addition of these last four in 2017, Legends Row was declared full for the foreseeable future.
The last time I walked down The Esplanade, I was struck by how many new condos have sprung up in that neighbourhood. I thought it may be interesting to put together a little photo journal of the structures I encountered that day.
Latest Comments
Great photos, Marvin. You really caught the people in great shots.
[…] you’d like to view more in-depth information on this sculpture on my TOcityscapes blog, click here). I always get…
Love this, these are good installations.
Well Well Well I had NO IDEA this type of thing was happening in Toronto downtown. I was really quite…
I agree with Bob K . And the weather was super warm . A perfect day for a parade. Being…