Stephen Bishop, who settled quite early on lot 42, was also District Councillor for the township during 1847-9. Wm. Larkin had been the first settler on this lot in 1824, but sold it to his cousin, Mr. Bishop, and moved to lot 4, near Kempenfeldt, about 1832.

One of the very first to locate within the borders of Flos was David McDougall, a retired coxwain of the Navy, who arrived on the 12th December, 1826, and took up lot 44 on this Penetanguishene Road. He was a native of Dundee, Scotland, and had served in the navy on the lakes during the war of 1812-15. Before he came to this county he had resided in Kingston, Ontario, where most of his family were born. As he was almost the first settler in Flos, the wolves were particularly troublesome in the early days of his settlement, and used to howl about the home of the lonely pioneer in a terrifying fashion. The bones of many sheep killed by these denizens of the forest were common sights in the rear of McDougall's clearing in those days. A son of his became the Methodist missionary to the Northwest Indians, the Rev. George McDougall, biographies of whom have appeared from the pens of the Rev. Dr. John Maclean, and his own son, the Rev. Dr. John McDougall. David McDougall and family left this place about 1842 and went to live in the vicinity of Owen Sound.

Beyond the swamp, northward, the Swan brothers, natives of the County Cavan, Ireland, and veterans of the 66th regiment, took up grants in 1836, and became early settlers,--Thomas on lot 51, and James on lot 52. Their brother, William Swan, settled in 1842 on lot 52, on the second line, and died, July 6, 1855, aged 47 years. James Swan died suddenly in 1840, leaving a widow, but no descendants. The sons of Thomas Swan are to be included in the roll of pioneers, viz., John O., (who died March 10, 1896, aged 65 years), James Thomas, jr., Joseph H., and William.

William Davenport, an escaped negro slave, settled on lot 51, at an early date, and became a prosperous farmer. His brother, Ben Davenport, had also been in slavery, and was unmarried.

On the next lot north, viz., on 52, George Hickling, jr., the eldest son of the pioneer of the same name at Crownhill, on the Oro side, was the first settler.

William Prey settled and opened a tavern on lot 53 in 1829. This was a welcome boon to wayworn and night over-taken travellers, but he did not remain here more than five of six years. And we find John Rowat on the same the lot, or a part of it, before 1837. Hugh Marlow, on lot 55, was the first postmaster in Flos, in 1837.

To the northward of Hillsdale of the present day, John Hamilton, a Waterloo veteran, settled on lot 60. On his retirement from the 79th Highlanders, at Penetanguishene, whither the detachment of his regiment had been sent in 1831, this lot was granted to him at the close of twenty-one years' service. His son James, who occupied the homestead, and another son William, of the same neighborhood, may also be classed as pioneers.

Beyond Orr Lake, John Rowley, a retired soldier with the rank of sergeant, received lot 70 in Flos, and became the earliest settler at this place. His son, who may also be included among the pioneers, contributed some interesting particulars of the early days to the Elmvale Lance of September 27, 1906. The hill at this part of the Penetanguishene Road has always had the name of Rowley's Hill, from the first settler.

Other retired soldiers also took up lots along this part of the road at an early period. James Gravett, of lot 73, was an old seaman, and wore his hair plaited in a queu, and hanging down his back, accordingly to the fashion of an earlier time. His second wife was a sister of the pioneer mail carrier, Neddie McDonald, of Penetanguishene. And on lot 74, Thomas Kettle, color sergeant of the 68th Foot settled in 1834.

In the early days of settlement, James Morrison kept the first tavern at Craighurst, which was then known as "Morrison's Corners." He was a native of the Island of Jersey, off the coast of France, and after living for a time in Barrie, where his relatives lived, about the year 1840, in addition to the tavern above mentioned, he also built the first mill at Craighurst, but it was not a success, as the stream was to small to supply good water power. He also started the first line of stages along the Penetanguishene Road in 1847, was the government contractor for the improvement of the road in the same year northward from his place of business, also had a sub-contract for carrying the mails, and had the government contract with Joseph Rush (a carpenter) for building the Indian houses on Beausoliel Island. He died March 26, 1856, aged 41 years; and his wife, Charlotte Johnson, survived him until July 25, 1892, dying at 79 years of age.

Alexander Laing, of Glasgow, Scotland, settled on lot 42, in March, 1821, and survived until August 13, 1877, dying in his 89th year. His son, John Laing, started a blacksmith shop at Craighurst in 1848. He died May 25, 1900, in ihs 82nd year.

Thomas Craig, with his two sons John and Thomas, jr., arrived in the spring of 1821, and took up lots 43 and 44. They were natives of Kendal, Westmoreland, England. Immediately to the north of their locations there was a wide swamp across which the Penetanguishene Road made its way, and this often bore the name of Craig's Swamp. It lent a dismal setting to the place in the pioneer days, especially in those seasons of the year when the wolves were most troublesome, particularly the autumn. Thomas Craig (the elder Thomas, there having been three generations bearing the name Thomas) died April 10, 1840.

John Craig, the eldest son, was a young man of 23 years of age at the time of their arrival, and settled upon the north half of lot 23, May 14, 1821. He was clerk of the division court at that place, and also postmaster, the post office (Craighurst) receiving its name from this family. He was District Councillor for Medonte in 1844, and was reeve of the same township for sixteen years continuously, 1851-66. During 1857 he was the Warden of the county. He died May 23, 1876, aged 78 years.

Thomas Craig, the second of the name, (there were only two sons in the pioneer's family) was the surveyor of the roads for Medonte and North Orillia in 1844 and subsequent years, and held other public positions at various times. He died August 23, 1871, aged 63 years. A considerable family survived him. Thomas, the third of the name, resides on the homestead; Abraham, Division Court Clerk, on the opposite, or Flos, side of the road. Arthur first entered the County Council in 1876 as Deputy-reeve of Medonte, and became reeve in 1878, a position which he held for several years. He was appointed Treasurer of the County in 1897, and held the position until his death, June 26, 1905, at the age of 63 years.

James Boynton, a native of England, settled on lot 51, in the second concession of Medonte, at an early date. Although he was thus not on the direct line of the Penetanguishene Road, there was a by road from it to his place, and accordingly he will be suitably placed here among the pioneers along the road. In later years, when relating the events of his life at the period when he moved with his family to this country, he said, "I had a log shanty, without floor or window; the door was so low I had to creep in on all fours." As there were no mills near his place, when he raised his first crop of wheat he had to take two stones and pound it, and from the meal they made a kind of coarse bread. At other times he would take a bushel of wheat on his back, with some provisions, and carry it to the mill, many miles distant, camping out at night. He died September 12, 1873, aged 77 years.

Hillsdale took its rise at an early date at the "regulation" place "where two roads meet," being at the point where the Gloucester Road left the Penetanguishene Road, and exactly half way from Kempenfeldt to Penetanguishene.

In the year 1829, Patrick Murphy, a retired soldier, came to this locality and settled. He had served under Wellington, and was quite a young man when he received his discharge with a pension of a "York shilling" a day, owing to a wound he received before the Battle of Waterloo. He died in 1874.

In the vicinity of Orr Lake, William Archer, a retired soldier, was the first settler, taking up lot 69 on the Medonte side early in the thirties. A numerous line of descendants of this name reside in this neighbourhood.

Here and there retired soldiers were settled along this Military Road, with wide intervals of forest between them. On receiving their quarterly allowance, these pensioners used to make things hum for a while as long as the pension installment lasted, and the Penetanguishene Road every ninety days was lively.

James Bowden, a veteran soldier, settled early on lot 80, Tiny. His son-in-law, John Stamp, son of the next pioneer, had this homestead for a time.

Marmaduke Stamp, a native of England, was the first settler on lot 85. He had not been a soldier, but as a civilian he was a useful person in his day. We ofter find him recorded as the overseer of the highway from lot 76 to lot 90, especially in the fifties. He was also a constable, and in other ways attended to the public weal.

Wyebridge took rise at an early period of settlement, the River Wye at this place furnishing good water power for mills. Angus Grant, who has been referred to in another part of this work as the husband of Catharine McDonald, the fur trader's daughter, kept an early store here for a time. He was well-educated, and had some good qualities, but did not succeed in business.

Robert Jeffs came with his family from County Armagh, Ireland, in 1820, to Penetanguishene, and soon after this time his son, Robert Jeffs, jr., became one of the first settlers near Wyebridge, on lot 95. Lot 96 also became their property, the father receiving one and the son the other. The wife of Robert Jeffs, the younger, was Phoebe Edmonds, the early Indian teacher at Holland Landing. He taught school at or near Wyebridge for some time, was District Councillor for Tiny in 1843-4-5, and again in 1849, and in various other ways served the public welfare. His sister, Hannah Jeffs, became the wife of William Wilson, another pioneer of this neighbourhood, and in West Gwillimbury, Edward Jeffs, another member of the family, was one of the pioneers of that township.

Arthur Crawford, a retired soldier, settled upon lot 100 in 1819, and was the only settler near the place for a while. He was a native of Belfast, Ireland, and died about the year 1835. Descendants of his still reside in this vicinity.

Edward and Miles McDonald were the early mail carriers from Penetanguishene. Edward was the occupant of lot 114, near the town, for a number of years. The other brother, Miles, went to St. Vincent Township, or Meaford, and spent the remainder of his life there.

David Bannister, a retired soldier, settled upon lot 76 at Waverley in 1829. He had served in Canada during the war of 1812-15, and had been at the Nottawasaga when the "Nancy" was sunk there. He was a native of Leicestershire, England, and after the war he returned to his fatherland, but came back to Canada with a wife and settled here.

Down to a late period the Penetanguishene Road passed through a long stretch of woods from Waverley to Wyebridge. In this lonely part of its course many years ago a tragedy occurred which has often been narrated, two soldiers having died here from fatigue and musquito bites. Their regiment was on the march to Penetanguishene, and when near Wyebridge of later times, one of the men fell ill and was unable to go any further. His brother remained to take care of him, but the others in the detachment pressed on and late in the night reached the post at Penetanguishene, In the morning, finding tbat the two brothers did not reach the post, a company of soldiers returned along the road to look for them, and on arriving near the place where they had been left the night before, they found them both dead, lying near together. Taking up their bodies, their companions carried them (about seven miles) to the post, and there buried them in the small graveyard on the hillside. At their graves they erected a headstone with this inscription

It is said that one of the men or perhaps both lived until they had arrived at Penetanguishene on a litter, although the popular account says they were both found dead. John Lethbridge, of Midland, wrote an account of the tragedy under the title of "Left to die," for which he was awarded the school prize for Midland Public School in the Montreal Witness competition, 1890, the article appearing in that newspaper.

Francis Dusome, the contractor for carrying the mails three times a week, owned lot 97 and lived near Wyebridge in the forties and afterward.

William Cowan, the pioneer on lot 98, has been already referred to in the chapter on the early fur traders.

John Smith, who settled on lot 106, had belonged to the commissariat department at Drummond Island.

So abundant are the memories and associations attaching to historical, old Penetanguishene, that volumes of matter, locally interesting, could be written upon that place alone. It would, accordingly, be impossible in these sketches to give anything more than an outline of the first years of that northern town. Many references have already been made to its pioneer days, in other parts of this work.

The first acquaintance of the present European settlers with the harbour of Penetanguishene was obtained when Governor Simcoe made his memorable trip to Georgian Bay in 1793. Little or nothing was, however, done in the way of using it until the war of 1812-15. Toward the close of that struggle a naval establishment was proposed for that point, and this may be said to have been the beginning of the town. Sir George Head was sent to superintend the commissariat duties of the new Establishment, and in his "Forest Scenes," published several years afterward, narrates his sojourn at Penetanguishene Bay. (His account occupies thirty octavo pages.) After a brief existence, the whole Establishment was broken up on March 10th, 1815, and not revived for three years.

The naval and military depot was moved in 1818 from the Nottawasaga River to Penetanguishene. Ten years passed during which the Establishment was conducted on a limited scale, and then the place received a sudden expansion by the removal of the military post from Drummond Island thither, the soldiers being followed by a variegated retinue of French and half-breed boatmen, traders and pensioners,- no greater mixture was ever found on any frontier. Many particulars of this migration in 1828 have been included in a valuable paper of 44 pages by Mr. A.C. Osborne (Papers and Records, Ontario Historical Society, 111.) (1901). In other articles, notably in a booklet on Penetanguishene (1907), Mr. Osborne's pen has done good service in building up the story of that town's early development.

A list of the detachments of regular troops stationed here at subsequent times may be found in the Rev. Dr. Scadding's Toronto of Old, p. 503, a book which has an interesting chapter on the place in the early days.

The Establishment, as it was called, was two miles beyond the centre of the present Town of Penetanguishene, and near the entrance to the harbour. Its situation is one of the most beautiful to be seen anywhere in eastern Canada, commanding as it does an extensive view of the arms of Matchedash Bay, with its picturesque and varied scenery. There was a stockade around the old post, but it was ruthlessly removed in the fall of 1906, and another building inside the stockade which was probably a magazine was taken down at the same time. A few of the original buildings of the post, are, however, still standing, notably the officers' quarters (a thick-walled, stone building, a storey and a half high, with loop-holes now bricked up). The barracks of the troops which surrounded the officers' quarters have all been removed, but at some distance the dwelling of Adjutant Keating, a hewed-log house of considerable size, is still standing at a little distance from the shore of the bay. The interesting little island, known as "Magazine Island," lies immediately in front, and on it may still be seen the old hewed log building formerly used as the magazine for the storage of the powder.

The first reduction of the Establishment took place in 1832, when the naval stores where put up at auction. From time to time reduction went on, until it came to an end in the early fifties, enrolled pensioners being the last stationed there.

On June 19, 1856, the Ordnance and Admiralty lands in various parts of Canada were transferred to the Province, and an Act of the Canadian Parliament (19, 20, Vict., c.45) enumerated and classified them. These included the reserves and barracks at Penetanguishene (5,396 acres), except that located by enrolled pensioners and under license of occupation to Major Ingall. This was by far the largest military reserve in Upper Canada, and very soon the Canadian Government converted it into a farm for a Juvenile Reformatory Prison. In 1859, we find the Reformatory fully established, and by October, 1860, it contained some 60 boys from various parts of "Canada West" as this province was then called. For the first few years the building used for the Reformatory was the old military barracks, in which the boys were cared for under Wm. M. Kelly, the Warden. A new and imposing structure was erected in 1862-6, and immediately occupied as the Reformatory. It was built chiefly of sandstone blocks from Quarry Island in the neighbourhood, but also with some granite and limestone, the central portion rising to a highth of 88 ft. Grants for the erection of the new edifice were made by the Canadian Government (in addition to maintenance) as follows:-

By the year 1866, there were 150 boys confined within its walls, and its population continued to grow.

Returning now to the early days of the Establishment, from which we have digressed, officers of many kinds came and went,-"birds of passage," we might almost call them,-yet some of those who came with the influx of 1828 from Drummond Island became permanent residents of the town or its vicinity, and they may well be regarded as its pioneers and entitled to some notice in these sketches. To this class belong Lieutenant Carson who was in command of the 68th, brought from Drummond Island, James Keating the adjutant, Santlaw Rawson, sergeant, and Captain John Moberly, R.N., who also came about this time, and was the agent of the Bank of Upper Canada (1836, etc.), besides being one of the early magistrates.

The officers of the Government Indian Department also came with the others from Drummond Island,-Capt. T.G. Anderson, Indian Agent, who lived here before going to Coldwater; Dr. David Mitchell, Surgeon-General to the Indian Department, and William Solomon, Government Interpreter.

Many other officers after getting their discharge papers became settlers in the adjoining parts of the country. To this class belong James Wickens, of the commissariat staff, and Samuel Richardson, the surveyor, both of whom, after the reduction of the Establishment about the year 1841, removed southward on the Penetanguishene Road and settled near Kempenfeldt.

Amongst others who held positions at the Establishment in those early years, was Capt. James O'Brien Boucher. At the close of the Establishment he took up land at Sutton, on the south side of Lake Simcoe, subsequently erecting a flouring mill and factories there. Sutton was originally named "Boucher's Mills," after this pioneer captain.

Another of those connected with the early naval Establishment at Penetanguishene was Dr. Caldwell. His widow at a later period, according to Dr. Scadding, lived in Toronto for a length of time.

Of the French-Canadian contingent who followed with the removal of the depot from Drummond Island in 1828, several became prominent in the early days of Penetanguishene. Dedin Revolte (Revol) built the first dwelling house in the town itself, according to one account, although there are two versions of the events; at any rate M. Revolte was the first French-Canadian to build a house. In the early days before a priest was regularly residing at the place, he instructed the people in religious matters, and acted as catechist in reading the service on Sundays. He also spent much time and means to instruct the Indians who were then so numerous in the neighbourhood, and mostly pagans.

J.B. Trudeau was the blacksmith for the Naval Depot, and was about 35 years of age when the removal took place.

Charles Vasseur was one of the soldiers, or at least had been one before the removal. It is said of him that he bought the first cow and the first yoke of oxen from the frontier part of the province to the new settlement at Penetanguishene.

Louis Colombes (Columbus) became the reeve of the united townships of Tiny and Tay in 1860-1, and was again reeve of Tiny in 1872.

In the paper by Mr. Osborne already mentioned, which deals more particularly with the French-Canadian contingent from Drummond Islandand their interesting experiences as canoemen and traders, there are to be found narratives by Louis Solomon, Michael Labatte, Mrs. Rosette Boucher, Jean Baptiste Sylvestre, Antoine Labatte and Angelique Langlade. The statements of these people have been permanently recorded by Mr. Osborne, with much expenditure of time and trouble, and the reader will find much interesting information in them.

Penetanguishene had been frequented by fur traders since the first permanent establishment of the military and naval depot there in 1818. William Beausoliel, trader, in 1819 settled on the island which bears his name, although the maps persist in calling it "Prince William Henry," while everyone calls it Beausoliel.

George Gordon, a Scotch trader who had been at Drummond Island at an earlier time, settled at the point a mile beyond the barracks in 1825, then built a house in Penetanguishene two or three years afterward, which was said to be the first house built in the town. Mr. Osborne's paper contains numerous particulars of this pioneer who died in 1852.

Two descendants of Dr. David Mitchell, the Surgeon-General to the Indian Department, became prominent in the early days of Penetanguishene, viz., Andrew Mitchell who built the first store in the place, and George Mitchell, who was Superintendent of Schools and died in 1868. Mitchell, the early storekeeper, was one of the moving spirits in the building of the first steamer at Penetanguishene in or about the year 1832.

William Simpson, the trader, was the first District Councillor for Tiny and Tay in 1843, going to Toronto to attend the meetings of the Home District Council.

Asher Mundy, who has already been mentioned in another chapter, kept the first canteen for the soldiers. Then Stephen Jeffrey had a second canteen, and was innkeeper in the early days at the town itself. He owned a vessel in the first period of the town's history.

From an early time there were three stores in the place, and in 1847 Edward Jeffrey added another. George Copeland had the first saw and grist mills, although there is an account of an earlier sawmill built at the head of the bay by Wm. Robinson.

Much has been written at different times literary visitors to that place, a partial list of whom is here given:
John Galt, Rev. Peter Jones, John Carruthers, Dr. Thos. Rolph, Mrs. Anna Jameson, Capt. Bonnycastle, Rev. A.W.H. Rose, Sandford Fleming, Dr. Scadding, and others. To reproduce the interesting references to the early harbour and town made in the writings of these people, would require more space than is at our command.

The religious welfare of the people does not appear to have been neglected in the early years. Ministers of all denominations on various occasions would journey thither to preach to the soldiers stationed there, and Walton's Directory for 1833-4 informs us that Rev. Lawrence Dempsey was the R.C. clergyman of Penetanguishene and the adjacent townships. The same volume also states that the Bank of Upper Canada had an agent there at that time in the person of Andrew Mitchell, Esq.

Coming down to later years, W.H. Smith, in "Canada: Past, Present and Future," gives a list of those in business at Penetanguishene in 1850, viz.: George Copeland, W.B. Hamilton, E. Jeffrey, Wm. Simpson, and Alfred A. Thompson.

Capt. James Matthew Hamilton of the 5th Reg. of Foot came to Penetanguishene about the year 1830, and was a prominent citizen there in the early years. His son, William Basil Hamilton, entered into partnership with James Darling and carried on a general store. He was District Councillor for Tiny in 1846-7-8, a Justice of the Peace, and held other public offices. On the construction of the railway to Collingwood in 1854, he removed thither, and entered the sawmill business. He held various public positions in Collingwood, being the first mayor in 1858. He died October 28, 1891.

Among other well known men of Penetanguishene in the early days, were two brothers, Alfred A. Thompson and Henry H. Thompson. Mr. A.A. Thompson was appointed a Justice of the Peace, April 3, 1857, and held various positions of trust during his life, which closed somewhat suddenly April 28, 1885. His son, Alfred B. Thompson, was first elected to the Ontario Legislature for Centre Simcoe in 1898, and is the present member for the constituency.

With a view to incorporation as a village, the County Council in June, 1875, appointed an enumerator to take the census of Penetanguishene, viz., Walter J. Keating, who found a population of 841 in the proposed limits of the new corporation. Accordingly, the Council passed a By-law incorporating it as a village. An Act to incorporate it as a town was passed by the Ontario Legislature, March 10, 1882, and on the third Monday after that date, the first election of Mayor, Reeve and Councillors of the new town took place.