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What Kingston Road used to look like in Toronto

Posted by Derek Flack / March 25, 2014

Kingston Road HistoryKingston Road doesn't pose much of a challenge from an etymology standpoint. Once the easterly route from Toronto to Kingston, the road dates back to the outset of the 19th century when Asa Danforth was tasked with building a route linking Toronto with the Trent River. While Danforth's road made it all the way east, it never really took and fell into disrepair soon after completion. 15 years later, Kingston Road was built following mostly the same path. During the almost two centuries that have followed, Kingston Road made up a huge chunk of Highway 2, a route that still cuts across Southern Ontario even though it was removed from the official highway system in 1998.

Once served by a radial railway, Kingston Road has always been an important street in Toronto. Businesses capitalized on the travellers making their way to and from eastern destinations, which afforded the Toronto portion of the street a rather vibrant retail scene earlier than other places to the east of downtown. It was also, rather naturally given its function, a place where some of Toronto's earliest tourist cabins were located.

The Kingston Road motel strip still clings to life today, but back in the 1950s it was positively booming. Prior to the 401, Highway 2 was a major east/west route through the province, and tourists were attracted to the cheap accommodation and proximity to the Scarborough Bluffs. These weren't rundown, shitty places. Take a look at the Roycroft Motel in the 1950s below. Now something of a concrete bunker, it's parking lot pool seems wonderfully optimistic and leisurely.

The whole strip of motels was, in fact, brimming with activity until the traffic dried up in the 1960s, thus mirroring the situation in the US with the rise of the Interstate. One suspects that the remaining motels will be gone in the next decade or so, depending on the level of condo pressure. The purge has already happened on Lake Shore, so that's not a particularly brave prediction to make.

Here's a look at Kingston Road when it was on the upswing.


2014325-king-west-malvern-1922.jpgKingston Road looking west from Malvern, 1922

2014325-king-west-vic-park-1922.jpgKingston Road looking west from Victoria Park, 1922

2014325-king-east-dixon-1922.jpgKingston Road looking east from Dixon, 1922

2014325-king-main-west-1922.jpgKingston Road looking west from Main St., 1922

2014325-king-hotel-midland-1922.jpgHotel / Halfway House at Kingston Road and Midland, 1922

2014325-king-scarborough-west-1922.jpgKingston Road looking west from Scarborough Road, 1922

2014325-king-Bingham-1922.jpgKingston Road and Bingham, 1922

2014325-king-south-brookside-east-1927.jpgKingston Road looking east from Brookside, 1927

2014325-king-east-lakeside-1928.jpgKingston Road east from Lakeside, 1928

2014325-king-west-birchmount-1928.jpgKingston Road west from Birchmount, 1928

2014325-king-east-to-brim-1930s.jpgKingston Road looking west toward Brimley, 1930s

2014325-balmoral-cabins-1930s.jpgEarly tourist cabins near Brimley, 1930s

2014325-king-west-from-lawrence-1930s.jpgKingston Road looking west from near Lawrence, 1930s

2014325-king-paving-1930s-east-toward-cliffside.jpgLooking east toward Cliffside, 1930s

2014325-112-114-king-rd-1950.jpg114 Kingston Road, 1950

2014325-roycroft-motel.jpgRoycroft Motel, 1950s

20131129-avon-motel-ed.jpgAvon Motel, 1950s

2014325-andrews-motor-lodge.jpgAndrews Motor Lodge, 1960s

20131129-park-motel.jpgPark Motel, 1960s



kioch / March 25, 2014 at 12:01 pm
It's so dreamy!
Fedora Man / March 25, 2014 at 12:14 pm
I like to take my internet girlfriends to the Hav A Nap.
TJ / March 25, 2014 at 12:20 pm
So it really hasn't changed too much? To people who complain about housing prices in Toronto, as of this past weekend, there are multiple listings of 2 bedroom townhouses along or very near Kingston Road for around $100,000 (some below and some just above). I think I saw a 3 bedroom townhouse for around $130,000.
Martine Plustwo replying to a comment from TJ / March 25, 2014 at 01:18 pm
TJ (are you the same TJ from The Dirty): Are you aware that those townhomes are projects?

Your last name doesn't start with 'M' does it?
lawd / March 25, 2014 at 01:36 pm
7th picture down kingston and bingham, all three of those buildings are still there. Thai resto, home, and a framing gallery at kingswood.

Todd replying to a comment from TJ / March 25, 2014 at 02:43 pm
They're cheap, but they're not great investments at all. Sure, you pay nothing for your house, but when you're robbed on your stoop each morning and forced to replace cell phones and vehicles on a daily basis, you'd wish you were house poor instead.
TJ replying to a comment from Martine Plustwo / March 25, 2014 at 03:03 pm
1.) No and
2.) I thought it would be, although my real estate agent friend informed me social housing projects are NOT allowed to be listed on MLS. Therefore, it could be some quasi-project.

To Todd:
All I was trying to do was make a point. I didn't say it was a great investment or a great place to live.
Todd replying to a comment from TJ / March 25, 2014 at 03:59 pm
What point? That even in Toronto there's affordable housing available if you're willing to overlook quality of life?

Brilliant. Is Detroit the same way too, you think?
?????? / March 25, 2014 at 05:11 pm
Couldn't this have been summed up by simply saying....
"Kingston Rd. Still looking like shit 100 years later"
loodle replying to a comment from TJ / March 25, 2014 at 09:26 pm
You don't want to live anywhere on Kingston Road unless you're west of Fallingbrook. The rest of the housing on Kingston Road are either projects or low-cost rental apartment buildings.
TEd / March 25, 2014 at 09:57 pm
Unless I am mistaken (and I may be) that "Hotel / Halfway House at Kingston Road and Midland, 1922" is now at Black Creek Pioneer Village.
Not Irish but I like em / March 25, 2014 at 10:03 pm
I live east of Fallingbrook (in my own house, there are million dollar houses south of Kingston facing the Lake) - agree that Kingston Road is a disgrace and look forward to selling and getting out. But it's a disgrace and neglected because around here very few people walk anywhere - I've lived on my street almost 10 years and have several neighbours I've never seen walk except to their car. West of Vic Park, there's street life with shops and coffee spots. Out here, no, except the odd drunk stumbling out of a couple of the local pubs.
Robbie Dee / March 26, 2014 at 09:09 am
East of Fallingbrook and South of Kingston Road, there are beautiful pockets with million dollar+ homes. There are a lot of new developments along Kingston Road that should hopefully improve the landscape. We are a Starbucks away from arriving. More affordable (and less insane)than the Beach proper and 13 minutes to the core. All while parking 4 vehicles in the driveway and enjoying 2,500 square feet and a pool. Check out Lakeside Avenue and tell me if there isn't value there. On the cusp, people.
Doreen Magliulo / March 26, 2014 at 11:55 am
I grew up on Bingham Ave. between Kingston Rd. and Gerrard in the late 30's and early 40's and have wonderful memories of that area. We did all our shopping on Kingston Rd. and it was a very safe and clean neighbourhood in those days. There was the Honeymoon Ice Cream parlour and Duckworth's Fish and Chips (the very best!) and Stedman's, a 5 and 10 cent store. We used to walk down to Kew Beach Park to swim in the freezing cold waters of Lake Ontario. It was a wonderful place to grow up!!
j.j. / March 26, 2014 at 08:38 pm
Its sad to see many people being so negative about Kingston rd and completely missing the point in this posting. Its a post war area and i love living here and i would never move. I have a big home within walking distance to the lake, ttc at your door, downtown a 25min drive and all the bonfires and clean air you can take in. I will sit in my yard and watch my house value skyrocket as cliffside village gets updated, while those who complain can move to oshawa.
Millie tavener / April 7, 2014 at 12:17 pm
I have lived on Kingston Rd, and now a block away for 50 years. Love living here, love the people! Will stay here ---God willing --- as long as I can. Millie Tavener
Cupcake / May 23, 2014 at 08:38 am
@Ted: You're right. The halfway house was moved to Black Creek Pioneer Village in the 1960s.
Nina / May 23, 2014 at 09:04 am
This makes me want to buy a place there! Just came back from NYC/stayed downtown- people made KILLINGS when they bought in the Lower East Side when it was considered a bad area...
Jeff / May 23, 2014 at 05:43 pm
"View from Kingston Road" a plate from a 2 volume edition of Picturesque Canada published some time around 1882, I live in the UK (originally from Canada) and found the books in a used, vintage book shop here and a few other late 1800's titles. Over 500 plates in these things, a few of them in Toronto, you can see what Kingston road looked like when it had carriages pounding along on it.

Julien replying to a comment from Todd / May 23, 2014 at 06:04 pm
Have you ever lived in a project Todd? How do you know you will get robbed each morning.

That has to be one of most rude and ignorant things I have heard in awhile and I wish people like you would not spread false information.


Julien replying to a comment from loodle / May 23, 2014 at 06:08 pm
There are lots of really nice areas along Kingston Rd. Its not all projects or low-cost rental apartment buildings.

I have lived in this area most of my life and I also work in real estate. I am willing to bet that most of the negative comments are coming from people who have never lived near Kingston Rd.


Beachboy R&R / October 7, 2014 at 12:34 pm
I must comment.I am a local Realtor who's office is in the Beach district and I must say that Kingston Road is not as bad as some of these people make it out to be. I've raised my family in both the Beach and in Cliffcrest area and I must say that our Cliffcrest experience was actually much nicer and safer than the Beach area. My car got broken into 5 times a year in the Beach and not once in Cliffcrest. In the beach we had a few swarmings on our street and lots of parking issues and lots of drunks walking around after the bars on Queen street closed.When we moved east of Brimley we got a bigger house for a lot less money and the kids grew up in a nice pocket. We've lived in Birchcliff Village just west of Warden for the past few 5 years and we love it. The Hunt Club golf course is right beside us, and it is spectacular. The neighbourhood is changing for the good with a bunch of new Condos going up and replacing a many of the old crappy buildings...there's still lots of work to do but they've started with the road work and will eventually finish with some nice Condos overlooking the Hunt Club and replacing the old Alpine Hotel with the new Kingston and Co condos. As far as the Condos along Kingston Road,east of Midland, some are good and some are not so good. 3311 Kingston Road( at Brimley) is a great building and it is safe. I've sold a few condos in there and that is a building I strongly recommend. In my opinion the ones closer to Eglinton may not be as safe. All along the south side of Kingston road there are some amazing pockets of homes that sell in the million plus range. Yes, there are some really cheap condo townhouse in the Kingston and Eglinton area, but some are safer than others. 180 Markham Road offers some of the cheapest real estate in the city, for what you get, but the issue is the housing building that surrounds it on the North side. Not all the people who live in there are bad, but there are some scary dudes hanging around these building selling drugs and weapons. There was just a murder last week in the stairwell of the building on Eglinton at Markham Road. This is the problem for the good people who live in the neighborhood.Just like any area you will get your fill of jerks, but overall I find if people are owning their units, they take better care of them. Part of the problem is that investors have bought a lot of the townhome condos and then rent them out to other people who really don't care as much and don't take car of the units as well as owners would. This creates problems for the good owners.If you have never driven down into the Hill Crescent pocket of homes before (which runs east and west from Bellamy Road over to the Guild area, south of Kingston road),you should definitely check it out. Lower Scarborough has some of the best real estate in the city...very affordable, safe neighbourhoods along the lake...Cliffside Village, Cliffcrest, The Guild, Hill Crescent, Port Union Village( off of Lawrence)...and I've also heard that the HAV-A-NAP Motel has been sold and is going to be turned into a condo project in the next year or two....
Dav / November 1, 2014 at 02:32 am
We have lived in the Guildwood area south of Kingston Rd near the Guild for 14 + years now. We love the area and we'll never wish to sell and move. In fact, we are thinking of adding a 2nd storey to our bungalow. Nice area, minutes to lake, bike trails, GO Station, TTC, kids walked to school, 1/2 hour to downtowncommunity. People generalize Scarborough out of ignorance. They are rough pockets in every neighbourhood in Toronto. That's the way it is if you want to live in Toronto. Look at Rosedale, probably the 2nd most expensive real estate in Toronto, but less than 1 km from Jamestown
Sam replying to a comment from Millie tavener / December 22, 2014 at 12:29 pm
I moved to 131 Eastville Ave. inj 2006. The old lady used to rent rooms in it. I was told it had originally stood on the south side of Kingston Road and was part of a motel. I suspect it is shown in the shot looking east from Brimley. I dont know if it might have been connected to "Balmoral Cabins" though I understood her to be Scottish. The house now faces west and is 75 feet south of Kingston Road.
I would be interested if someone had some local historical knowledge regarding the house.
ZiggyPup / January 9, 2016 at 05:06 pm
We have just moved to the Cliffcrest area from Avenue Road and Lawrence. We used to live in the Beach proper before that but found you could get double the house fir your money here, In addition to that, we've found a wonderful neighbourhood that has a pot luck street party in the summer and a winter solstice street party. We feel safer and more welcome here than we ever did in our old, supposedly upscale area. I think if we want to see the revitalization of Kingston road, we need to form a citizens group and come up with a plan to pitch businesses on moving here. The neighbours in the area are very keen to support local, so if we get involved, that's how we'll bring change, not by being critical on Facebook.
Gwenn Faulkner replying to a comment from Doreen Magliulo / January 10, 2016 at 07:10 pm
I also grew up in the Kingston Rd./Victoria Park area... ( on the "Scarborough" side)... We lived there from 1936 to 1949... during WW2... went to Blantyre & Courcelette schools, then on to Scarborough Collegiate... We were a large family... Our road was not yet paved,although Vic.Pk. was... It is where we feel that we grew up... We were poor & didn't know it... But it was a safe neighbourhood that still holds such fond memories for my brothers & I...Our dad was a WW1 veteran who suffered from the effects of dirty trenches & mustard gas,etc... We enjoyed the local merchants like Shaw's Delicatessen as well as the Blue Bird Bakery & Hunt's & so many other small shops,as well as a Loblaw's store... and Heddon's Hardware... it was all there... no real need to go anywhere else except to hop on the streetcar & go downtown to Eaton's or Simpson's & the Santa Claus parade... I am now nearly 88 yrs old & have lived in many other places... but none with such memories as Meadow Ave...
David Berry / January 22, 2016 at 01:16 am
I grew up in the Cliffside area in the 1950s, when that part of Kingston Road was a vibrant retail strip with the atmosphere and amenities of a decent small town (even allowing for my childhood innocence). We lived near the Bluffs and I knew every trail down the to the lake, as well as delivering the Toronto Star at various times from the bottom of Birchmount to Midland Ave. I'm so sorry to hear the negative comments on this page...hey, it's a big city folks, and Scarborough always had enormous diversity, of all kinds -- as well as enormous vitality and hidden places which I will always remember and treasure after 40 years of living at the other end of the country (Victoria, BC)
Russell Farrell / February 17, 2016 at 07:47 pm
I lived on 17 Burnley avenue for a few years then moved to 94 Tower Drive about 1958 and lived there until 1981.I went to Buchanan Public School and Wexford Collegiate. I now live in Angus Ontario. I miss Toronto and visit the old neighbourhood every so often. Google VE3ELL to contact me if you knew me.
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