Learning Unit: Transportation
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Kingston Road and Transportation


Some Regional and Contextual Background Information

  • The first thoroughfares on Scarboro Heights were Indian trails -- dating back almost 10,000 years. The McCowan collection of arrowheads and other points includes evidence that suggests that the Fenwood Heights Blvd. / Kingston Road area could very well be the earliest known site of human occupation in Toronto. These ancient artifacts could tell a story or two! (See also Dr. B. Schroeder, Evidence for Early Human Presence in Scarborough, Scarborough Historical Notes and Comments, V13 #1.)

  • Until 1834 Toronto was called “York”.

  • Kingston Road was first blazed by William Cornell, Levi Annis and other early settlers along the front of the Township in about 1800. A good portion of the original “ Front Road ”, as it was initially called, was in the lower area or “flats” below the hill which marks the old Lake Iroquois shoreline east of Markham Road. Danforth Road was sometimes referred to as the “Back Road”.

  • The Annis family were probably the very first white pioneers in Scarboro. They chopped a clearing out of the forest near the present Washington United Church in about 1793. Several tales from the annals of this family are interesting for their references to travelling along the “front” of Scarborough two centuries ago.

  • In late 1832, Rev. William Proudfoot travelled between his home near York and what is now called St. Andrew’s Presbyterian Church in the McCowan Road and Lawrence Ave. area. He was considering the possibility of becoming their full-time Minister. He had arrived in York from Scotland in September 1832. See also Transactions of the London and Middlesex Historical Society, Pt. VI (1915) and Pt. XI (1922) or Scarborough Historical Notes and Comments Vol  8 #3.

  • In 1815-17 Kingston Road was improved and given a second alignment, generally to the north of the first.

  • In 1836-37 Kingston Road was straightened to its present alignment and “planked” with thick boards. The roadway was sixteen feet wide.

  • The free land grant policies of the period 1793-1826 had been unsuccessful in effectively settling Upper Canada. The enormous government land reserves and the holdings of speculators resulted in a scattered population immediately beside the St. Lawrence River and Lakes Ontario and Erie. The scattered and mobile form of the population hampered development of educational and other social institutions. Beginning in 1826, a policy of selling Crown Lands to the highest bidder was initiated, although the free grants to Loyalist and military claimants continued.

  • Beginning in 1831, policy was directed to preventing poor settlers from buying land on credit -- the theory being that only those with ample capital could properly improve the land. It was more important to the economic development of the colony, argued Edward Wakefield, to have a ready supply of wage labour than to have a population of poverty-stricken freehold farmers. Land prices were therefore set just low enough to attract the farmer with capital and just high enough to force the poor into a landless labouring class. Wakefield's theory was further adopted into economic policy through the Land Act of 1841.

  • This policy of holding land prices out of reach of ordinary immigrants was intended to create a labouring class. A readily available working class was necessary, according to Wakefield , to attract development and investment capital from Britain -- public construction projects could not be built without labourers.

  • One of the major public works of the mid-late 1830's was the improvement of the Kingston Road, the most important land route in the province. (see also When the Ground Fails)

  • According to their obituaries, James Weir (1814-1897, from  Lesmahagow, Scotland , 1833) and James Neilson (1820-1897, also from Lanarkshire, about 1832) were partners in a Scarborough land-clearing enterprise for several years in the 1830s. Contracting by the job, “James could cut, split and pile his three cords per day”. These two professional “bush-whackers” probably cleared a fair bit of land along the front of the township. Indeed, it is entirely possible that at least Weir was contracted to clear parts of the alignment for the “new Kingston Road” when it was straightened in 1836-37. James Weir bought his first farm in 1845. The Neilsons first lived on the lakeshore near Highland Creek.

  • In 1855 the Grand Trunk Railway bought about an acre from Robert McCowan toward the north end of the farm. Two years later, the GTR bought another 3 acres. The train station was probably built on the latter parcel. The Grand Trunk was eventually absorbed into the CNR.

  • According to a McCowan family story, David Purdie, father of Jenny McCowan, purchased a car in 1911, only the fourth in Scarborough.

  • On Anniversary Sunday, there would likely be a few former members at the Church service, some perhaps from outside the Township.

  • Ruth Evelyn McCowan (1883-1972) was the only surviving daughter of Robert McCowan Jr. and Hannah Ashbridge. Her husband, Jack Heron, served in France during the First World War. Ruth kept Jack up-to-date on Scarborough news with her many letters written from her father’s farm. Their children were Margaret, Ruth and Jack.

  • William “Harold” McCowan was the second son of Robert and Hannah McCowan. Until 1950 he and his older brother, Robert Ashbridge (Ashley), farmed the almost-200 acres on the east side of McCowan Road between Eglinton Ave.  and Lake Ontario .

  • Ashley McCowan and his wife, Flo Green, and sons Walter and Frank lived in the re-built farmhouse (1917) that still stands at 23 McCowan Road.

  • Harold and his wife, Janet (Jenny) Purdie, and their family (Bob, Jack, Helen, Bill and Jim) lived in the huge Queen Anne style farmhouse that stood until 1975 at 3100 Kingston Road on the east side of where Arby’s is now. (This house (built 1914) replaced the regency cottage in which William Ewart Young was born. Mr. Young was a co-founder of McLeod, Young, Weir a prominent brokerage firm. He was a grandson of Andrew Young.)

  • The parents, Robert and Hannah McCowan, lived in the third farmhouse, built in 1916, which was on the west side of Arby’s.

  • Hannah Ashbridge McCowan was born on her father’s homestead, lot 26 concession B, about a mile west of her husband’s family farm.

  • William “Billy” McCowan was Robert’s younger brother. He spent his last years driving radial cars along Kingston Road .

  • By 1901, the Toronto Railway Company had extended the electric radial line to the Half-Way house at Midland Ave. The “stop” numbers at that time were not as they are today. “Stop 19” today is at McCowan Road. “Stop 19” at the time of the 1919 fatal accident was at Courcelette Road.

  • Refer also to The McCowans’ Who’s Who for 1992

  • Refer also to R.R. Bonis, A History of Scarborough, 1965, p. 255-277 “Old Scarborough Roads”

  • Refer to our Transportation page and Information Processing program

  • Go to our Search page -- use your language and critical thinking skills to define helpful search criteria


Pioneer Travel, 1800-1835

One member of the family, Levi, was a little better equipped than usual, took his mount, a horse, and before daylight was attacked by wolves; he slung himself from his mount into a branching tree, and with flint and steel stood off the pack till daylight. The sun was a great defender. Another member, Jerry, had not so far to go and in the darkness wended his way homeward along a familiar trail, crossed by a large fallen tree, along which he carefully felt his way, and then jumped fully five feet to the accustomed path, the spot had become the rendezvous of a settler's large drove of hogs and his unexpected intrusion created a panic, and hastened his arrival at his father's cabin.

Annis Annals

(William Annis) was a dispatch and mail carrier from Toronto to Oshawa, mounted on a horse, and who had many encounters with highway robbers and later, before the construction of the Grand Trunk Railway, he drove the Royal Mail Coach from Toronto, east over a corduroy road, that was afterwards planked with four inch pine, laid on cedar mud sills, which proved to be a high point in the development of good roads. But with all the prevailing banditry he never lost a mail bag.

Annis Annals


The day exceedingly cold. Hard frost, the trees coated all over with ice, and many of them beaten to the ground by the weight of the ice. Took five and a quarter hours to go to Scarborough [St. Andrew’s] --  twelve miles -- on horseback. The roads were bad.

Diary of Rev. William Proudfoot, Dec. 1 1832 (in Transactions of the London and Middlesex Historical Society, Part VI (1915)


Walked from Scarborough home. Took six and a half hours... The frost began to give way in the morning and by the time I got home they were wrought mire.

Diary of Rev. William Proudfoot, Dec. 3 1832


The road for three miles, ie from York to the forest the very worse road I ever saw. The mud at the least four inches deep, and so thin that it's surface was quite smooth. For four miles through the forest, it was pretty good, but from Mr. Brownlee's to Mr. Thomson's [beside the Church], was wretched. In consequence I was spattered up to the knees and was very much indisposed in consequence of the ride [on horseback].

Diary of Rev. William Proudfoot, Dec. 8 1832


It had freezed all night. The roads were exceedingly rough and in those places where they were in pools yesterday the ice was not yet strong enough to bear the horse. As the best way of getting on I walked a great part of the way and led the brute. This saved much pain to the animal and, perhaps, some broken bones to myself. By the time I got to York the snow was falling so heavily that I could scarcely see my way.

Diary of Rev. William Proudfoot, Dec.19 1832


The Labouring Class and Capital Projects, ca 1837

In the demise of the late Jas. Neilson, Scarboro has lost one of its earliest settlers, one who away back in the thirties helped to fell, clear and fence hundreds of its acres of primeval forest. He and his partner, the late Jas. Weir, in that early day were noted bush whackers. Both boasted of making the foundation of their wealth by clearing land and chopping cordwood in Scarboro. For the cordwood they received 25 cents per cord and the price for clearing land was in the same ratio, yet both died wealthy.

James Neilson obituary, 1897, Pherrill Scrapbook


William Jess, a native of Norfolk, England, emigrated to Canada June, 1836, and was first employed by Richard Beatty on the construction of the Kingston Road in Scarboro and was dubbed “Billy Go The Road” by his fellow workmen, presumably from the fact that he was tramping around in search of employment when first seen in Scarborough .

David Boyle Collection


John Duncan ... left Tyrone Ireland in 1836 ... not having any friends or acquaintances here he had to trust to Providence for someone to give him employment. He first hired with Arch Muir on a farm about 9 miles east of Toronto on Kingston Road [in Scarborough at Bellamy Road] ... In the spring of 1837 Elizabeth, his wife, and 3 children left Ireland ... made their way to Toronto and then to the farm of Mr. Arch Muir where her husband was still at work and lived there for about 1 year, then moving to Lot 2 Con 2 on Kingston Road ... and was living there at the time of the straightening of the Kingston Road, helping to break the first stone that was put on the road.

David Boyle Collection



The Auto Arrives

Chesters have been making a grand trade of their horse, buggy, harness, wagon and sleigh for an Overland automobile.

Ruth McCowan Letters, October 27 1916


This is anniversary Sunday and the church was full this morning. We had our own choir, and Dr. Tanner sang a solo... There were not so many at church tonight, but Ashley [McCowan] says he thinks there must have been thirty cars there... Harold is getting a new car this week, a Ford.

Ruth McCowan Letters, June 17 1917


Ashley and Mamma and Papa drove out to Mount Albert. It rained a good deal yesterday and the roads were not very good, but they made the trip each way in about two hours. I remember when we used to take old Maud. We would leave home about eight or nine and would get there about five in the afternoon.

Ruth McCowan Letters, June 24 1917


They sold the cattle this week. Seven of them at $.14 per pound, and weighed at Neilson’s. [Mr.] Vivian [a cattle dealer] took them to the market and got $15.40 per cwt, but they had lost about 100 pounds. Some price for beef, eh what? It is almost twelve o’clock and the automobiles are still on the go. This afternoon Ashley counted 75 go past here in 15 minutes. It has been like a procession all day and I don’t see much pleasure being in it. I often wonder how it is so many people have time to go motoring now, when there is so much work to be done and so few to do it. Of course there are always more on Saturday and Sunday.

Ruth McCowan Letters, May 19 1918


The Kingston Road traffic was always heavier on weekends in the summer. The men had quite a time getting the loads of hay across the road from the opposite field. As there was a little slope on the lane up to the road, the horses had to stand there straining while the cars went by. I remember once the load upset but thankfully no one was hurt. On Sunday nights we often sat on the verandah and watched the “jam-ups” as we called them. Being a single lane each way [before 1935], it was stop-and-go for the cars for miles. We always referred to McCowan Road as “the sideroad”.

Helen McCowan Thomson, 1990


Papa had a two-car garage at his house. But I don’t believe he ever drove a car. Even though we had a big driving shed of our own and Uncle Ashley had a long implement shed, both Dad and Uncle Ashley “had to” keep their cars in Papa’s garage. We had to parade across the orchard to get into the car. I think the Dads didn’t trust us kids fooling around inside the cars if they were parked at our place. Aunt Cynthia and Uncle Alex Thom got his sister’s old green Chev when she died but no one at Uncle Alex’ drove. By this time I had learned to drive but didn’t have a licence. Once in a while Uncle Alex would ask Mom and me to come down to their place at Dunbarton on the Gray Coach Bus. I would drive us in the old chev out through the country visiting our Annis relatives. When Uncle Alex died, Auntie decided to give me the car. We named it “Gertie”. I didn’t drive it much, but when the war was over Jack drove it to Toronto to work every day. I remember the Willy’s-Knight that Dad had. It seemed to be bigger than a coupe and was a dreadful mustardy brown colour. A tool box was built onto one end of the back seat. Bob and Jack sat on the seat. They were the oldest. Bill and I had to sit on the edges of the tool box with our legs in amongst the tools. Bill rode backwards -- I guess he was too young to complain.

Helen McCowan Thomson, 1990


Our early ‘20s Willy’s-Knight was one of only two ever made of that particular model -- at least that’s what we were told. Dad bought it at the estate sale of the Ames family at Kingston Road and Main Street. Ames were a well-known brokerage firm. It would never seem to start when it was damp out. We would have to push it outside to let the sun dry things off. Uncle Ashley’s ’26 McLaughlin, on the other hand, would always start no matter how damp it was. The Willy’s-Knight was so big and heavy that Uncle Ashley called it “the freight train”.

Jack and Bob  McCowan, April 2001, as told to Bruce McCowan


We finally stopped using the grand Willy’s-Knight and parked it in the garage. We hadn’t driven it for 3 or 4 years when quite a regretable incident occurred. It was during the depression and General Motors was going around buying up old cars. They wanted to get the old cars off the road in order to stimulate sales.

There was also the argument that these older cars (such as our Willy’s-Knight) that had two-wheel brakes were dangerous -- if the guy in front had a new car with four-wheel brakes and you only had two-wheel brakes, it was quite likely that you could rear-end him. The back fender of four-wheel-braked cars had to carry a red triangle warning drivers behind that they had four wheel brakes -- ie “leave lots of room” if yours only had two-wheel brakes! Most cars for the working-man got four wheel brakes in about 1928.

In any event, one day a GM guy came in to our place and walked into the garage. I saw him pick up a crowbar and smash a hole in the engine block of the Willy’s-Knight just to be sure that no one ever drove it again.  GM did not even want to take it away.

Eventually, the top and the engine were taken by a wreckers. The rest of it finally got pushed into the gully south of the house to help stop the erosion. An old Model T went into the ravine too.

Dad and Uncle Ashley had quite a good working partnership on the farm. Dad loved horses and would use only them to work the land -- I only saw him drive the tractor once. Uncle Ashley, on the other hand, never seemed to use the horses -- he enjoyed driving the tractor. Of “the Dads”, Uncle Ashley was the farm mechanic.

Bill McCowan, April 2001, as told to Bruce McCowan


Two-Wheel Brakes, A Radial Car and Tragedy, 1919

Lack of evidence last night at the Morgue caused the adjournment of the inquest into the death of Elizabeth Caroline Bell, who was killed on June 29 when an auto-truck in which she was riding was struck by a radial car at Stop 19, Kingston Road. Testimony given showed that at the time of the fatality, the truck driven by Samuel Barnes, now in hospital with a broken collar-bone, was heading from the lake and ran straight into the street car, in charge of Motorman William McCowan. The truck was hurled into a tele-graph pole and overturned, Miss Bell being thrown upon her head. She sustained a fractured skull.

Newspaper clipping, believed to be 1919, supplemented by an interview with Clark Secor, March 2, 1984




Individual Exercises

1) In 100 words, compare the difficulties of road travel in the pioneer days with road travel today.

2) Re-read the paragraph above which begins and ends: “One member of the family, Levi ... and hastened his arrival at his father's cabin.” Now rewrite this paragraph in a way that you feel is more understandable.

3) If you were in charge of “planking” Kingston Road with boards in 1836, how many trees would you need to cut down to plank one mile of the road? State the sources of your data and explain your assumptions.

4) Draw a sketch showing the way in which Kingston Road was “planked”.

5) What do you think happened when the Grand Trunk Railway was built? The construction of the Grand Trunk Railway and the construction of the Don Valley Parkway 100 years later had somewhat similar economic effects on Scarboro Heights. Explain. Look for physical examples today on Kingston Road.

6) Who was “old Maud” and how was her role about to change?

7) How did the arrival of the “car” affect social life in the farming community?

8) Write a 100 word paragraph on the importance of good brakes on a car. Refer to some of the engineering principles that are involved. 


Class Discussion

1) Discuss the merits of the government labour and land policies of the 1830s.

2) Discuss the future of the motels along Kingston Road.


Field Trip and Research Paper: Landforms

1) Ask your parents to take you on three short drives in your neighbourhood.

  • Drive a) Drive to the south end of Meadowcliffe Drive. Then go back to Kingston Road and go west.

  • Drive b) Drive to Fairmount Park (south on Dorset to Sloley). Walk through the Park toward the bluffs. Go back to Kingston Rd then west to Midland .

  • Drive c) Drive south on Scarboro Crescent to Scarborough Bluffs Park .

What was different about Drive b? How is this significant regionally? How did Scarborough Heights Blvd get its name? How would you find the 3 highest points of land within a 30 mile radius of Scarboro Heights? Find them.

2) Refer to our Scarboro bluffs pages starting here; Bonis A History of Scarborough (p.1-14) Morrison The Bellamy Bluff; and McCowan A Lakefront Estate Residential Development in Scarborough Historical Notes and Comments V13 #2.

3) Write a 500 word essay on “People and the Scarborough Bluffs”. Be sure to give your essay a “people” aspect.

Research, Analysis, Writing Assignment: Transportation c1837

Describe a corduroy road. Discuss the pros and cons of making the Kingston Road into (a) a planked road and (b) a macadamized road. Discuss the importance of road improvement to the growing City of Toronto and to the Township of Scarborough. Suppose the planking of Kingston Road had been delayed twenty years. What effect might this have had on the development of (a) Toronto and (b) the Province? Output the results of your analysis to a 300 word essay. List your resources. Note: Refer also to R.R. Bonis, A History of Scarborough, 1965, p. 255-277.


The Scarboro Heights Record V13 #12