There is a few small mentions in the history of Penetanguishene to a Captain Borland. Seems he captained a steamship, a paddle wheeled vessel, out of Penetanguishene at one point. This ship was called the Penetanguishene, and it ran between Penetanguishene and the indigenous town at Coldwater. But in researching him I found so much more!

I enjoy finding the average guy who does amazing stuff without much notice. Andrew Borland, seems to be just that. he was Captain of steamships, the Colborne and the Penetanguishene. The former on Lake Simcoe, which went between Hollands Landing and Orillia and the later that went between Penetanguishene and Coldwater. Andrew Borland, born 1795 in the USA he first came to Newmarket about 1808. At the beginning of the war of 1812, Andrew enlisted and became part of the York Volunteers. Serving with the 1st York Militia, under Peter Robinson. Peter Robinson would choose men to join a rifle detachment, which remained attached to the 1st York Militia. Andrew was chosen. Rifle companies were special Ops, they did not wear Red coats, like their musket carrying compatriots, but wore a Green coat in recognition of their status. Muskets were preferred for general infantry. Rapid fire of the inaccurate guns often spelt victory. Rifles, could be fired similarly, but also could be used both in the line to pick off special targets and in operations that were a little more guerrilla in nature. Andrew Borland was present at the surrender of Detroit, where he received a medal and was also at Queenston Heights, on October 13th 1812, where he was wounded. This battle was also where Sir Isaac Brock was killed. Indeed Peter Robinson and the York Militia were Commanded by Sir Isaac Brock himself, and in his company proceeded to Detroit, where Hull Surrendered. William McCay kept a journal of the events: The war years

On August 8th 1812 finds Peter Robinson's rifles near Long Point, on the 9th, they were joined by Sir Isaac Brock, and would continue on towards Detroit, where they landed at Kettle Creek , six miles from Port Talbot. The company, exposed to the elements would sleep either in the open or in boats. Neither seem appealing to me! Finally arriving on the 14th of August, sunburnt and tired, William McCay writes:

The 1st, Riflemen under Peter Robinson would be closely attached to General Brock, and later Lieutenant Robinson would write of his men:—
“This body of men consisted of farmers, mechanics and gentlemen, who before that time had not been accustomed to any exposure unusual with persons of the same description in other countries. They marched on foot and travelled in boats and vessels, nearly six hundred miles in going and returning, in the hottest part of the year, sleeping occasionally on the ground and frequently drenched with rain, but not a man was left behind in consequence.”
Perhaps their best eulogy is in Brock’s own words: “Their conduct throughout excited my admiration.”
Later the same year, at Queenston heights, the Militia under Captain Cameron heard the tell tale sounds of battle. Mustering his troops, they were on the road to the battle when a horseman approached and waiving his arms made the command to follow with expedition. This was General Brock himself and later, in his final moments, uttered the words "Push on the York Volunteers!" (from History of York Rangers Above) Some remember this as perhaps his final words or orders.
On the left flank of the Volunteers Colonel McDonnell was mortally wounded. They would see him carried off by Captain Cameron. The Yorks had rallied a mile away from Queenston, but once again turned to the battlefield and though smaller in numbers, join the battle once again under General Sheath. again they would be mentioned in despatches. Andrew Borland would be a hardened soldier, battle tested to the max. But still not yet 25.
From there the York Militia would move back to York Proper, although what they found there was not a stronghold.
So imagine what Andrew Borland thought when the warning guns sounded and fifteen ships appeared over the horizon. Though not strongly set up for defense, the York Militia were asked to defend York.
But, General Sheaffe in assessing the situation, realized that York was lost and ordered it's abandonment. Again we go to the History of the York Rangers:
It was this duty of abandonment, which Sir Roger Sheaffe performed in a fashion that endangered his regulars, disqualified the militia for the rest of the campaign, caused the burning of the parliament buildings and ruined Sheaffe’s own reputation as a soldier. Unless he purposed to match brown-bess muskets against the guns of a fleet—he must have known he could not prevent a landing and the capture of the ridiculous fortifications. But as it was he frittered away what fighting chance there was by allowing his force to be engaged and beaten in detail. First, Major Givens with about forty Indians and a few inhabitants of the town not enrolled for military duty, then about sixty Glengarry Fencibles, then some two hundred and twenty militia, and fifty of the Newfoundland Regiment, then two companies of the 8th Regiment (about two hundred strong)— these in succession were dribbled in to withstand a landing force upwards of one thousand strong. Meanwhile General Shaw, with forty men and a six pounder held the line of Dundas Street and never got into action.
So was Andrew Borland one who had been sent to repel the large invasion force on the 15 ships? It would seem he was either there or close to the Block house that was destroyed, as he received 6 wounds that would stay with him the rest of his life. Some reports have him and Asher Mundy blowing up the Blockhouse that day.
The same day that Andrew Borland was injured at York, his future partner William Roe was also being heroic.
In 1807 William Roe came to York. During the war of 1812, he was instrumental in concealing from the invading American force, under General Dearborn and Commodore Chauncey, a large portion of the contents of the public treasury. He was at that time employed in the office of the Receiver-General, and by the order of the Government he buried three bags of gold and a quantity of army-bills, on the farm of Chief justice Robinson, on the Kingston Road. The enemy afterwards-secured the bills, but the gold was safely restored to the authorities by Mr. Roe when the Americans had withdrawn. He also removed the iron chest of the Receiver-General's office to the house of Donald McLean, Clerk of the Assembly. The latter was killed in battle, and his house plundered, about one thousand silver dollars being taken from the cheast https://www.electriccanadian.com/history/ontario/york/part03chap11.htm
Sergeant Borland was decorated and rewarded for his patriotic and eminent services in Detroit, York and Queenston heights. But that wouldn't be the end...
Andrew was still a young man, but his injuries would make him too lame to continue in the services. So undeterred, he would quickly use his military connections to launch into another business. The Fur Trade.
In the coming weeks after his last battle, William Roe and Andrew Borland would start trading with the Ojibway up in Hollands Landing, forming a firm of Roe and Borland (or Borland and Roe, they would use both) which would see incredible profits for the time. Eventually, Roe, Borland and Borland's old Commander Peter Robinson, along with the JohnCawthra family would establish the New Market. And it would eventually be called Newmarket, as it is now.
It would seem that at least William Roe would also have a Public house built, the tavern would be called the Borland and Roe Tavern. (it was destroyed by fire in 1845, would be the site of the Forsyth Hotel and today a bar named the George)

With a base in Newmarket, they would travel up to Holland Landing to trade with the Ojibway. The partnership would also open a fur trade post in Coldwater. Where the family of his Chippewa wife Mary would meet to trade furs for goods. Living in Newmarket, Andrew Borland was made captain of the
Colborne that made a regular trip from Hollands Landing to Orillia. In 1827, he was given patent for land in Barrie.

In 1834 local merchants in Penetanguishene, Andrew Mitchell and A.A. Thompson, built a steamboat to go from Penetanguishene to Coldwater. Captain Andrew Borland was commissioned to be master of this new ship, the Penetanguishene. The steamship would leave Penetanguishene in the Morning, arrive in Coldwater in the afternoon and return, stopping briefly at the military establishments on the return voyage. Borland and Roe would also have a hand in the overland route, the nine mile Portage. " The portage route would continue to be used by local fur trade companies P&W Robinson and Borland & Roe of Newmarket in 1824: where " fourteen year old Thomas Williams and an African-Canadian man named Ben, working for contractor Alexander Walker, would make many round trips each week along the portage route transporting goods"

However getting back to Andrew Borland, despite his injuries, would see his partnership with William Roe thrive and along with his old commander Peter Robinson and the Cawthra family, profitable to all parties.
Along the way, Andrew would meet a young woman named Mary. They would eventually be married. This partnership would also thrive quickly, as a son John would be born in the first year of their marriage. This son would follow in his fathers footsteps, becoming a ships captain.
Andrew had land in New Market and a trading post in Coldwater, but he also had 6 debilitating injuries from the war and so he sought other employment. In 1823 he became a steamboat Captain, the Colborne which travelled between Hollands Landing and Coldwater. The family would also grow by one with the birth of another son, who they would name William.

The ship was to travel daily between Penetang and Coldwater. It would also at the mercy of it's owners, and would stray as far as Sault Ste Marie and St Joseph Island. On one of these trips, the Penetanguishene would finds it's way to another destination it hadn't intended, the bottom of Georgian Bay. Reported sunk, it may have just been stuck on a rock, as the Penetang was refloated and continued into active service.
On another trip, this time headed towards Owen Sound with the Labatt family in tow they would see the lines parted and would lose the family by Christian Island. Louis George Labatte would eventually make it to shore at Thunder Bay (by Lafontaine) and become settlers there. The other families there would make it to Owen sound and start a community there. In 1834, they had another son, they named George, and a year in 1835 James was born.
Penetang became an area of importance in the fur trade of the Day. As shown above, by 1860 the fur trade would see Penetang be a major player. for Andrew Borland he would be recalled to service of his country, 1837 would bring rebellion along Yonge Street, Andrew, under the command of Gerald Alley, would see him with 200 warriors mainly from Orillia and probably his wife's people follow them down to Holland Landing.
The 1837 Rebellion arose and former militia, like Andrew Borland was recalled and he being in a good relationship with the native people, having married a Chippewa woman and knowing the language, was put in charge of 200 native warriors. With loyalties uncertain the crown would turn to it's old native allies once again, and once again they would prove their loyalty, only to be betrayed again. But that is another story.

At the time, Penetang was still a military village, with other settlers including half-breed (metis) from Drummond island. Captain Borland would fit into both worlds, being in a half-breed marriage and a veteran of the war of 1812. It has been told he knew the ojibway language. And evidence like a marriage to an ojibway woman is quite solid support of that. These ties would come in handy on his trips between the Military town of Penetang and it's half breed community and the native reserve of Coldwater, which even led to Captain Borland and Andrew Mitchell buying the sawmill of Chief Assence in Coldwater.
When a contract to build houses on Beausoleil island was tendered, Andrew and his son John would get the contract and build houses on Beausoleil island.

Later in the year 1865 Captain John Borland, Andrew's son would the be asked by F.S, Darling, son of J S Darling, clerk for Andrew Mitchell, to Captain a new boat out of Midland, the Maid of Midland. Continuing the family history of steamboat master piloting between Midland and Waubashene. The small ship would run Baron Von Hugel up to Midland to assess the feasibility

of a railway into that town. This service would continue until 1876, when the train would provide a more direct route into Midland.
Captain and Sergeant, the steamboat Captain and Military Sergeant, Borland would not go quietly, well not without having a fascinating end. There is a family plot in Coldwater, his wife is there listed as Relict, which is an old fashion way of saying widow. So presumably he had died, and in fact his last listing on the census has him in Coldwater in 1858. But no grave marker has his name listed anywhere. So is he buried there, unmarked, or is he somewhere else, maybe buried at sea (Lake) somewhere? Penetanguishene (Steamboat), 23 Sep 1834: Maritime History of the Great Lakes
Art Duval Pipesmoke of the Past

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