Original purpose of road was to connect Toronto with Penetanguishene for military reasons
Penetanguishene Road was the original Yonge Street and one of the first roads opened in Ontario.
In fact, the lower part of the road, stretching from Barrie south to Bradford and then down to Toronto, was referred to by the local settlers as "the Penetang Road", even into the 20th Century. Even when its official name was Yonge Street. Everyone knew where it went, not Toronto, but to Penetanguishene.
Etienne Brule was probably the first European to travel this lower route in the early 17th Century under order from Samuel de Champlain. Old French maps of the area show routes travelling from Fort Rouille, at the Exhibition Grounds in Toronto, along the Humber River north to about where Nobleton is today and then across the Oak Ridges Moraine to the south-westerly branch of the Holland River and north through the Holland Marsh, Bradford and into Lake Simcoe.
For centuries before then, the First Nations Ottawa and Huron had been travelling north from Lake Simcoe and up to Georgian Bay by one of two primary routes. One went to the head of Kempenfelt Bay, where they would take the Nine Mile Portage across to Willow Creek at the eastern edge of Minesing Swamp to the Nottawasaga River to Georgian Bay. The other route went northeast to about where Orillia is today and then along what is Highway 12 to where Coldwater is and down the Coldwater River to Matchedash Bay and Georgian Bay.
When soldiers and settlers carved the road out of the old forest, its main purpose was to connect Toronto with Penetanguishene for military reasons.
In 1793, John Graves Simcoe became Lieutenant Governor of Upper Canada. A veteran of the American Revolution, Simcoe brought many of his 1st American Regiment, which became the Queen's York Rangers, to Toronto to help with engineering projects like road building. In 1795-6 they blazed the trail for Yonge Street.
Yonge Street's first incarnation was the route from Toronto to where Holland Landing is today. Its main job was to allow quick communication between Toronto and Lake Huron/Georgian Bay via Lake Simcoe through the old First Nations portage routes.
But the War of 1812 underlined the drawbacks of not having a safe, secure passage from the lower lakes to the upper lakes. The numerous portages, while not a problem for light and nimble travellers like First Nations people and their birch bark canoes, were a hard haul for British troops wearing woolen uniforms and carrying supplies. A more reliable land route that could bear heavy wagons, horse riding couriers and items like large ship anchors and cannon would be crucial for the province to defend itself.
A road from Lake Simcoe north to Georgian Bay and a harbour would be necessary. Simcoe identified a place east of downtown Barrie, which he named Kempenfelt, as the start point and Penetanguishene as the end.
Thomas Williams, one of the first settlers in Simcoe County, eventually settled along the Penetanguishene Road just north of Barrie. He eventually retired in Orillia where he wrote a series of articles about his early days in the county for The Orillia Packet, before it merged with The Times. One of his 1893 articles reads:
"As near as I can now ascertain, the first real settlers those who took land with a view of making homes and deriving their living from the land came to the country in the year 1819. Some may have come in 1818, but I can find no proof of such coming. Our family came in 1822. The land was "taken up," that is, ours was selected and a location ticket obtained from the Surveyor-General and Crown Lands Office, in the fall of 1821. When we did reach it and built our shanty, I can distinctly remember our neighbours (and the whole settlement for the first 10 miles at least were neighbours). All knew each other and went in and out of each other's dwellings, and were interested in the affairs of each other; and most of them spoke of coming three years before. A few had been a shorter time. This applies to all the settlements along the Penetanguishene Road. At or in the vicinity of Penetanguishene there were some few families which were not of the military or naval forces stationed there. They were of the class which the soldiers there would have called civilians. Some might have been considered a sort of camp-followers, carrying on some sort of business or mechanic art, and deriving their living in that way from such works as were carried on in connection with the Naval and Military Establishment."
Samuel Lount Soules wrote a similar series in The Barrie Examiner in 1901 that mentions the Penetanguishene Road experience - meaning the road running south from Barrie, which later became known as Yonge Street.
Soules tells the story of Moses Hayter, a grocer from London, England seeking a better life, who travelled to Ontario's backwoods via ship, landing in New York City and made his way inland to Toronto. There, he made his way to, "the Crown Lands Office where he could obtain a lot of Government land. He was advised to seek information from some of the oldest settlers who had taken up land in some of the recently surveyed townships in the County of Simcoe.
"From Toronto he pushed on as far as the Holland Landing, and from there he came on as far as Myers Corners, now the village of Stroud. Now at this time my father, David Soules, had settled upon lot 26 in the 14th Concession of Innisfil, on the south shore of Kempenfelt Bay, generally known as Big Bay Point, and had been there about 10 years. At this time there was no road from there to Myers, only a very blind trail which was occasionally used to reach the Penetanguishene Road (which itself was scarcely fit to be called a road at the time). Myers advised Hayter to see Soules, who would advise him what was best for him to do, and the shortest way to reach Soules would be by this trail, seven miles through an unbroken forest where wolves and bears were very numerous. Now I make this statement to show the courage, perseverance, and determination of this new comer.
"The whole journey from Toronto had been accomplished on foot, and now, not daunted by what Myers had told him of the probability of his getting lost in the woods and lying out all night, he boldly set out on this perilous jaunt and at dusk reached the desired destination. I shall never forget it, as I was lying in bed sick with the measles.
"Hayter gave an account of what he had passed through and what his business was. And in those days when there was but little communication with the outside world, we were pleased to meet with strangers, especially one like Hayter who was to us a full encyclopaedia, and one that was always ready to impart to others such information as was most enjoyed. My father told him there was a 200-acre lot joining his that belonged to the Clergy Reserves. It was excellent land, and he had good reason to believe that it would soon be placed on the market for sale.
"And as preemption rights were then recognized, he would advise him to make application at once for the first right to purchase the lot. Hayter did so and received a favourable answer. He at once engaged a man to chop four acres. My father promised that they would make a bee and get it logged and burnt off as soon as possible, so that he could build a house on it, (lot 25, Concession 13)."
Lieutenant Col. William O'Brien writing in The Barrie Examiner remembered some of the early settlers along the Penetanguishene Road and Wilberforce Street, which ran parallel to Penetanguishene Road, to the east in Oro Township:
"There was a settlement of coloured people in the central part of the township, of which Wilberforce Street, named in memory of the great emancipator, and which will be found in the description of many old deeds, is a reminder. These people were escaped slaves. Some here may remember the name of Jenny Jackson, an old lady of very rotund proportions. It is of her that is told the story of a hand to hand, or rather hand to paw conflict with a bear over the body of a pig which Bruin was feloniously trying to extract."
In her diary, O'Brien's wife, Mary, recalled that Jackson chased the bear away with nothing but a broom after the bear knocked the pig right through the front door of her cabin.
Lieutenant Col. O'Brien also noted a winter shortcut on the Penetanguishene Road:
"In winter the ice formed the best road across the lake. Sleighs coming down the Penetanguishene Road crossed the Bay at Kempenfeldt, landing on the other side near Tollendal, and thence making a short cut through the woods to the Innisfil Road, the highway to the south. From any part of Oro this would be a two days journey, but from Barrie, when the sleighing was good, the drive of sixty miles was often accomplished in one day."
Over time, settlers, commerce and tourism supplanted the original purpose of communication with the military at Penetanguishene. The road has remained an important regional route, but with much of its history forgotten.
Kempenfelt is now just a small part of eastern Barrie, with a plaque to mark its place near the waterfront, across which hundreds of soldiers and sailors of the British Army, Royal Navy and provincial militia and marine, marched. Franklin travelled through on one of his Arctic explorations.
In Penetanguishene, once the home of warships like the H.M.S. Tecumseth and H.M.S Newash, and a number of regiments from the British army, including some that fought at Waterloo, the Military and Naval Establishment remains a tourist attraction.
But landmarks that stood for decades have been slowly removed, like the Craighurst Community Hall, recorded in Ian McInroy's 2012 article in The Barrie Examiner:
"For almost 135 years, the Craighurst Community Hall has been the hotspot in the village north of Barrie for everything from games of euchre, sendoffs and receptions for soldiers in wartime and travelling entertainers making their way up and down old Penetanguishene Road during Simcoe County's early years.
"But time took its toll on the post and beam structure, built on a stone foundation, that sits on a parcel of land so small, it's 'not much larger than the building's drip line,' says Sheila Craig, a sixth-generation Craighurst resident, whose family first moved to the area in 1821.
"Earlier this year, the venerable hall was finally declared unsafe by the township, after structural shifting was noticed in the winter, and closed to the public."