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For many years before a settlement was made at or near Long Point, Major-General John Graves Simcoe, the Lieutenant-Governor of Upper Canada, proposed to found there a military establishment, to aid in the defence of the new province. He had heard favorable reports of that district long before he had the opportunity of personally examining it. He constantly advises the Home Government of its importance, as for example in the letter written on December 7th, 1791, shortly after his appointment, he says:  "Toronto, the best harbor on lake Ontario, and Long Point, the only good road-stead on Lake Erie, are admirably adapted for settlements. These and the country between the Grand River and the La Tranche (Thames) form a body of most excellent land, of which no grants have yet been made."  ("Dominion Archives," Q. 278)

In another letter (August 20th, 1792), accompanying the proclamation dividing Upper Canada into counties, etc, he announces his intention to occupy in the following spring a post near Long Point, and another at Toronto, and to settle himself on the river La Tranche. ("Dominion Archives," Q. 278, p. 197. "Simcoe to Dundas," No. 11).

About a year afterwards, he again sends to the Home Government a favorable notice of Long Point, saying,  "The survey of the communication between Lakes Ontario and Sinclair (St. Clair) is completed. The surveyor has discovered an admirable harbor on Lake Erie, near the very place he (Simcoe) wished it, namely, Long Point, opposite Presqu’ Isle. (August 23rd, 1793).

On September 20th of the same year, Lieutenant-Governor Simcoe submitted to the Home government, an actual survey of the Thames, so far as it serves to communicate between lakes Ontario and St. Clair, referring to the tract of land as "one of the finest in America," and, accompanying it a survey of Long Point, on Lake Erie, saying, "the situation of Long Point is eminently suitable for a fortified post and naval arsenal for Lake Erie, and the establishment of one here would counteract the one held by the United States at Presqu’ Isle. A harbor could be constructed on the island near it. It possesses every facility necessary for an important centre of military operations!"  ("Dominion Archives," Q. 279-82, p. 483). Towards the close of this long epistle he again reverts to the settlement at Long Point as affecting the movements of the Indians. "The settlers to be brought in should be brave and determined Loyalists, such as those from Pennsylvania and Maryland, who at the end of the war were associated to support the cause of the King, and who had sent an agent to ascertain what arrangements could be made for their removal to the province. A strong settlement there would effectually separate the Mohawks on the Grand River from the other Indians."

In a letter, about two years after (July 31st, 1795), to the Earl of Portland, Simcoe emphasizes the importance of the occupation of Long Point as a naval arsenal, saying,  ‘I am thoroughly convinced that it is absolutely necessary that military establishments should precede settlements, and hence I have withheld all grants on the centre of Lake Erie. There should be a military organization established there at once, and around it a strong settlement could group itself. The half-pay loyalist officers with their followers will form a proper basis for the settlement at Long Point. I propose to put Major Shaw in command of the troops and in general superintendence there."

In another letter, written at the same time, to Lord Dorchester, he announces his intention to visit the intended settlement near Long Point, and in view of the fact that three hundred troops of Pennsylvania are at Presqu’ Isle to construct a fort at the entrance of the harbor, he asks leave to send a detachment of the Queen’s Rangers (one hundred rank and file) to Turkey Point, which is considered to be the most eligible situation.

During the summer months of 1795, Lieutenant-Governor Simcoe made his long-deferred visit to Long Point and the Grand River. In a letter written on his return to Lord Dorchester from Navy Hall, he describes his route and the country through which he passed. His favorable preconception of the district was not disappointed, and he became more than ever anxious to found a settlement there. "The country is thickly timbered, the chief trees being oak, beech, pine and walnut. Making our way through the forest we reached the lake at a place which, from the abundance of wild fowl, is named Turkey Point. A ridge or cliff of considerable height skirts the shore for some distance. Between this and Lake Erie is a wide and gently sloping beach. The long ridge of hard sand (Long Point proper) encloses a safe and commodious harbor.  The view from the high bank is magnificent. Altogether the place presents a combination of natural advantages and natural beauty but seldom found. Here we have laid out a site of six hundred acres for a town, with reservations for Government buildings, and called it Charlotte Villa, in honor of queen Charlotte."  In this letter was enclosed a sketch of Long Point and a plan of the proposed town.

In a despatch from the Earl of Portland to Governor Simcoe (December 6th, 1795) the proposed settlement at Long Point was formally approved, as was also the class of settlers proposed. "The gentlemen mentioned in your letter of the 30th of July, as desirous with their followers of settling there, cannot fail to lay the best foundation of attachment to the Crown and constitution"  ("Dominion Archives," Q281, 2);  and a month later, in another despatch,  "His Lordship urges that the occupation of Long Point should take place with as little delay as possible (January 6th, 1796).

The intention of Lieutenant-Governor Simcoe to found a military settlement at Long Point was frustrated by Lord Dorchester. His Lordship, in a despatch from Quebec (April 4th, 1796), declares that "the present posture of affairs would condemn growing expense or leaving troops in Upper Canada to increase the growth and prosperity of the colony. The policy of placing so many troops out of the way, and the enormous abuses in the public expenditure for twenty years, are not the only objection to this mode of encouraging settlements. The principle itself is erroneous, as evidenced by the improvement in provinces where neither extraordinary expenses were incurred nor troops were employed for civil purposes. We have no intention of authorizing public works of great expense, but reserves of land should be made at every place likely to become of consequence, where they may be required for public purposes."

In a despatch to the Earl of Portland (June 18th, 1796) Simcoe states plainly that his plan as to Long Point had been frustrated by the interference of Dorchester. "It is my public duty to observe, that in the civil administration of this government I have no confidence whatsoever in any assistance from Lord Dorchester. His economical ideas are contrary to the real principle of public saving."

It is unfortunate that this difference of opinion existed, for it prevented the early establishment of strong military posts at such places as Long Point, London and Chatham.

The settlement at Long Point was assuredly tedious in its beginning, but it was not thereby doomed to be forgotten.

Lieutenant-Governor Simcoe obtained leave of absence, owing to ill-health, in the summer of 1796, and sailed for England. The Hon. Peter Russell, president of the Executive Council, was appointed acting Governor.

The townships in various counties were surveyed into allotments, and among them Walsingham, Windham, Townsend and Charlotteville.

Up to this time no grants of land had been formally assigned in Norfolk County. There were a few squatters already there. "Dr." Troyer, Frederick Mabee, Peter Secord, Lucas Dedrick, Edward McMichael, Abraham Smith and Solomon Austin. These were confirmed in the possession of the farms they had already chosen. Now proclamations were issued inviting settlers to the New districts, and appealing especially to the United Empire Loyalists.

The fees for land grants, a much discussed question, were settled by an enactment of the Executive Council for Upper Canada, in 1798, as follows:

"Council Office, 25th October, 1798.

"That grants to be issued in consequence of Orders of Council subsequent to the 6th instant, to U. E. Loyalists and their children of the first generation, to the extent of two hundred acres each, are not to be charged to the expense of survey, but are to be subject to a fee of threepence per acre, and that one-half of the above fees are to be paid to the Receiver-General by all persons on taking out their warrants of survey, and the other half to the Secretary of the Province on receiving the patents for the land ordered them.

"Approved and signed, "J. Small,
"Peter Russell. "C. E. C."

The fame of the Long Point district had reached to Eastern Canada, and when it was opened for settlement there was for a few years a steady influx of settlers, chiefly Loyalists from the Lower Province, for whom it was a second migration. The great majority had lived already in New Brunswick for ten years or longer. That province was over-crowded, and the allotments unsatisfactory; and so, being influenced by the offers of land in Upper Canada, they came west, for the most part in open boats, to make their homes in that district.

But this removal was a work of stupendous difficulty. The roads were simply blazes through the forests. The heaving bosom of the inland sea was the only highway, and they had to trust themselves and their dear ones in frail batteaux to the deep waters. Only one man came to Long Point in the later years of the century who had ever been there before, that is, the old Scotch soldier, Donald McCall, whose history is related in a subsequent chapter. Consequently, their knowledge of the course was meagre and the danger great.

Those who came by land had to find their way over the devious trail of the Indian. Their worldly possessions were tied up in portable bundles, and carried often on their shoulders. The length of their journey precluded their bringing much with them, and thus the building of their new homes in the County of Norfolk was just as tedious and just as severe as it had been years before in their settlement on the St. John.