Owen Sound in the 1850s

Jennie Fleming, the youngest of the Fleming family who settled in 1850 at Kilsyth, Derby Township, had deep memories of her pioneer days.

“As a frequent visitor in the early days to Owen Sound, Derby’s market place, she saw this hamlet on the arm of Georgian Bay grown from a little village of Sydenham into the thriving commercial town and city of Owen Sound. She sometimes recalled the fact that at first on entering the town she had to cross the Sydenham River on a log where the Second Avenue bridge [sic] now stands, and walk deep in mire on the main part of Poulett Street.”(1) [Roy Fleming, 1942]

Roy Fleming more than once recalled that in Owen Sound’s early days his Aunt Jennie crossed the Sydenham River by traversing – very carefully, we might surmise – a felled log, and then in town having to deal with the muck of the main street. One can imagine Jennie, a vital woman who lived into her nineties, reflecting on the changes she had witnessed since her arrival to the forested wilderness – walking long distances as a teenager, driving horse-drawn buggies on gravel-covered roads in her twenties, travelling by express trains to Toronto in her seventies.

Felled trees probably served as bridges in more than one spot – and in those years the tree could be at least three feet in width and easily tall enough to reach from bank to bank.  In 1841, according to Paul White in Owen Sound: The Port City, it was possible to cross the Sydenham River on the west side of town by tree. He wrote, “The only easily accessible crossing was to the south of the new community, at the present day site of the mill dam on 2nd Avenue West. Here, a tree had been felled and travellers could pass over the river by walking on the bridge created by the fallen log.”  (2)

Jennie wasn’t the only one to comment on the mud. James McLaughlin told the story at an Ontario Historical Society meeting in Owen Sound in 1920 about his first visit in 1854 – “On coming into town there were very few houses, and the main street, now Second Ave. East, was a mass of mud. A single plank ran up and down each side of the street. In stepping off the plank to let a lady pass he went in so deeply into the mud, he pulled his boots off in getting out.” (3)

No wonder – Sydenham, its former name, was situated on a vast swamp. As one visitor wrote of his visit in 1851 – “much of the place was a dense thicket or swamp of cedars which originally occupied the whole site of the present city… All the district around both railway stations was a vast marsh with willows and black snakes.” (4)

Now we ask: When did Jennie make her trip, where exactly did she cross the river, how did she get there?

When the Flemings came to  Derby Township in 1850 Jennie was only seven years old – too young for such a walk. More likely her memory dates from when she was a teenager between 1855 and 1860.

Curiously, there is very little written about the early roads and bridges into Owen Sound, but it is probably safe to assume that the main county roads in Derby had been cut, if not fully cleared, by 1855.  Jennie’s older brother William described taking grist by wagon to the Inglis Mill possibly around 1851.(5) Therefore, Jennie likely walked the current County Rd 18 to Rd 5 (which goes toward Inglis Falls where the Mill was), turned  north, through the woods that would become Harrison Park on the right and Greenwood Cemetery on the left, and then crossed the Sydenham River where the road connects to 2nd Avenue East. From there it was a straight course to Poulett Street (later renamed 2nd Ave E.) and the centre of town. This is a distance of 11 to 12 km from Kilsyth – a fair day’s hike to market.

Route from Kilsyth to Owen Sound crossing the Sydenham River on 2nd Ave E. (C 1855)
Route from Kilsyth to Owen Sound crossing the Sydenham River on 2nd Ave E. (C 1855)

It took a few years for the Town Council to replace the tree (or something equally makeshift) with a proper bridge.  There is this record for June 1871 – that “Council ordered contractors Sadler and Showell to build a bridge over Poulette (2nd Avenue E) street at a cost of one thousand dollars.” (6) The bridge was in place by 1880 as we can see in the photo below. Interestingly, what had been forest in the 1850s was completely gone.

View of Owen Sound in 1880 looking north on 2nd Avenue East where bridge crosses the Sydenham River. Source: Owen Sound the Community View (Owen Sound: The Ginger Press, 2007). Photo courtesy Wayne Woyce.

The bridge today is known as Jubilee Bridge. I have not been able to determine when it received this name  – possibly after  Queen Victoria’s Golden Jubilee in 1887, although  it wasn’t the name Roy, who knew Owen Sound well, chose to use when he wrote “The Passing of a Pioneer” on Jennie’s death in 1942.

Jubilee Bridge at Owen Sound, 1910. Courtesy Toronto Public Library
Jubilee Bridge at Owen Sound, 1910. Courtesy Toronto Public Library

We could easily  drive Jennie’s walk  following the map above. We could also make the outing much more pleasant by combining the drive with hikes on trails in Harrison Park and Inglis Falls to get a taste of what Jennie would have experienced on her walk. See Owen Sound Tourism, Park Trails to plan a trip.


  1. Roy Fleming, “The Passing of a Pioneer : The Worthy Life of Aunt Jennie Fleming”, 1942. [Fleming Family Papers]
  2.  Paul White, Owen Sound: The Port City, (Toronto: Natural Heritage Books, 2000), p 14
  3. James McLaughlan Sr. “Reminiscences of Owen Sound and its District,”  Ontario Historical Society – Papers and Records Vol 18 1920. p. 12. McLaughlan later opened confectionary business in Owen Sound and sold throughout the Bruce and Grey counties.
  4. Robert Crichton, “Impressions of Owen Sound in 1851.” Ontario Historical Society – Papers and Records Vol 18 1920. p. 11
  5. William Fleming, “Story of the Emigration of the Family of Alexander Fleming – Jean Stewart from Scotland to Upper Canada,” c. 1927 version 3   [Fleming Family Papers]
  6. Melba Morris Croft, Fourth Entrance to Huronia: The History of Owen Sound, (Owen Sound, 1980) p. 123

2 thoughts on “Owen Sound in the 1850s

  1. Do the Fleming Family Papers include any of the hand written books that C.A. wrote later in life? I recently read about them in Dorothea Deans’ biography of him and would love to read more of recollections.


    • Hi Paul – which books do you mean? We have typed “essays” on family members that he wrote as part of the intended family history – but that might not be what you mean. He did write several business texts that were used in the Northern Business College that might be available through Owen Sound Public Library and of which we have 2 or 3. Good that you have read Deans’s biography. Can you tell us more of your interest, please? We might be able to help.


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