Easy transportation by land and water, seems to have played a considerable part, here as elsewhere, in the location of early settlements. The only means of communication in the neighborhood of Oshawa in the days, previous to 1800, appears to have been by water. Canoes, small boats and rafts by which to paddle along the shores of Lake Ontario were the only known method of locomotion, apart from walking. Hence the early settlers naturally took up their first abode along the Lake Front. In 1793, Gov. Simcoe planned, for military purposes, the road between Kingston and Toronto, now known as the Kingston road. As soon as it was made possible as a means of travel the incoming settlers shoved their way back from the lake and located at desirable points along their original highway. Many years previous to any attempt at settlement the French had established trading posts along the North Shore of Lake Ontario. Notably at the mouths of the streams at Port Hope, Oshawa, Darlington, Frenchman’s Bay, and the Humber ; the latter place still shows the ruins of an old French fort built in 1749.
The Indians in those days paddled up the streams as far as possible and then betook themselves to trails which led to Georgian Bay and the Northern districts where trapping was indulged in during the favorable seasons of each year. The furs were brought down over the same route and, at the trading posts, were exchanged for such articles as in those days were found to be most desired by the aborigines. The real objective of the Indian was Oswago or Albany where they came in touch with the English merchants, with whom they contended that they could make a more satisfactory bargain than with the French. It was to intercept them while on their journey, that the trading posts were thus scattered along the North Shore of Lake Ontario by the French merchants of Montreal and Quebec. Throughout central Ontario there appears to be no doubt that Port Hope was the first permanent abode of the Anglo-Saxon since the capture of Quebec by Wolf. As early as 1778 a flourishing trading post was in existence at this point. A small Indian village was located there by the name of Cochingomink, inhabited by the Mississagua tribe. Peter Smith was the first white man to leave any enduring mark of his existence in that locality. He was widely known as a trader and trapper and lived in a log hut on the east side of the little stream known as Smith’s Creek. “The date of his arrival at Cochingomink, cannot now be definitely ascertained ; but he was succeeded in 1790 by a man named Herchimer, who took possession of the but and carried on the fur trade established by his predecessor.” Early settlers to the east of Oshawa are said to have patronized the Grist mill at Port Hope, and to have conveyed their store of flour, upon their backs, from there to their lonely homes in the Woods at Darlington.
The village of Colborne appears next in the order of places to boast of the presence of a permanent white settler. Dr. Caniff says, “Joseph Keeler, “the first settler,” came from Rutland, Vermont, about 1789. He afterwards in 1793 brought in forty settlers with him, amongst them Greeley, a surveyor ; built a saw-mill, flouring mill, carding and woollen mills, oil well and distillery, near the mouth of Keeler’s Creek, now Colborne Harbor.” Coming nearer home we can give no more authentic nor concise account of the earliest settlements surrounding Oshawa than to quote from an historical sketch of Ontario County published in 1877 by J. H. Beers & Co., Toronto. “At the end of the revolutionary war, many families who had settled in the States, remained true to British connection, and were persecuted by the triumphant insurgents for their loyalty. There was a general confiscation of their possessions, and they were driven to seek homes elsewhere. Many of the refugees settled in Canada, after undergoing terrible hardships, and were known as United Empire Loyalists. Other Americans sought a home under the British flag, from less patriotic motives. They discovered the sunny spots along the shores of the lake, found out the soil was good, drew their 200 acres of land, and rations from the nearest fort or garrison, for a period pf three years, and had no objections to be classed as U. E. L.’s, although their sympathies were altogether with the “patriots.” They became excellent settlers, and throve on the virgin soil of Canada. Not a few of this class entered and took up their abode in the County of Ontario, during the years of calm that succeeded, and have been erroneously claimed as persecuted U. E. L.’s. They, however, in course of time, and their families became good British subjects, and at this distance of time it would be a difficult as !well as an unnecessary and ungracious task to point out who were the real and who the pretended loyalists, who found out they were likely to fare better under the proclamation of Governor Simcoe with the disbanded soldiers and loyalists than in the struggle for a home in Uncle Samuel’s dominions. The family of Benjamin Wilson, claiming to be a U. E. L. the first known settlers, came into the township of Whitby in 1794. He was a Vermonter, born in the town of Putney, in that State. For a couple of years he had no other near neighbors than Indians, and they appear to have been somewhat troublesome. The first year the Indians came and carried off the whole year’s provisions, which had been supplied the family by the Government. The poor people were driven in terror from their little settlement down the lake towards the Bowmanville or Barber’s Creek. The Indians were a band of Chippeways. The Chief, Wabbokisheco, who had been absent when the settlers shanty was looted, on his return compelled the Indians to give up the provisions taken away, and make ample payment in furs for such as had been consumed. The Chief also gave Wilson a peace belt to hang up in his shanty, telling him there would be no danger in future as long as the belt was kept in sight. And neither was there ; the Indians became most friendly, and supplied the family afterwards with abundance of venison and fish.