Simcoe County history

By Tom Villemaire, Special to Postmedia Network

As Simcoe County was evolving and growing, individuals often left their marks on the region.

One of these people was Jacob Gill, who built the stone barracks at Penetanguishene. Much of what we know of Gill comes from an article his daughter wrote (under the name “Mrs. Leonard Wilson”), published Feb. 29, 1912, in the Orillia Packet, and from British Army records.

Gill arrived in Canada in 1811, from Vermont, joining the British army as a commissary. He was sent to Simcoe County in 1814 to improve the Nine Mile Portage from Kempenfelt Bay (which would soon become the site of Barrie) to Willow Creek Depot.

Gill was tasked with building large boats and even ships for the British at Wasaga Beach, where the British would build Schoonertown. During his first winter in 1814 at the depot in the woods, he and two men were left to guard government supplies. The harsh conditions meant the supplies to feed the small crew ran out before spring arrived. So, they left Willow Creek Depot and made their way northwest to Wasaga along Willow Creek and the Nottawasaga River, then along the shore of Nottawasaga Bay to Penetanguishene. There were no roads or outposts or even First Nations settlements along the way. But the crew survived and was rewarded with a new posting: Travel to Fort Gwillim, where Holland Landing is today, to build storehouses and docks.

Gill then settled at nearby Newmarket, but while his young family remained there, he made his second trip to Simcoe County, arriving in Coldwater to build the grist mill, which still stands, for the local First Nations who were being encouraged to settle in the area.

In 1829, Gill took his family to a new job at the Establishments in Penetanguishene. He was contracted by William Robinson to build a sawmill on what would become known as Copeland Creek near Penetanguishene; the mill was to cut lumber to build the government buildings, barracks and officers’ quarters at the new military and naval base.

Their journey from Newmarket to Penetanguishene — tracing a route from the south end of the county to its very northern edge — gives you an idea of how easy movement was in old Simcoe County.

Leaving Newmarket on a Monday morning, the family reached Holland Landing, seeking shelter for the night in a “deserted government building.”

Next morning, they embarked on a schooner with all of their possessions, including Gill’s tools, to travel up the Holland River, through Cooks Bay and across Lake Simcoe to Kempenfelt Bay and up to the head of the bay, where a small cluster of huts and sheds stood at the start of the Nine Mile Portage. They travelled all of Tuesday, arriving in what would become Barrie on Wednesday afternoon.

After they offloaded the schooner, the family built a fire and cooked their supper, then moved their possessions into a shed owned by a man named Sullenger. They spent the night with Alexander Walker, a Scot. Walker ran a transport business along the Nine Mile Portage, using ox carts. Walker put the family up in his unfinished home, and contracted to haul their possessions across the portage and then forward them by water to Penetanguishene. Walker was one of the first full-time residents of Barrie and had a large log cabin on the hill overlooking the bay near Sophia Street, not far from what would become Bayfield Street.

Thursday morning, the family was bundled onto one of Walker’s lumber wagons and hauled east and north to Dalston and Kerridge’s Brewery. Walker dropped them off there where, according to the Packet article, “A negro named Smith agreed to take them to Penetanguishene, and after various vicissitudes and spending another night in a partially finished house, they reached Mundy’s canteen (in what would become Midland) late after dark on Saturday night. In passing through what was known as the Nine-mile bush, the children rode in the waggon while the elders walked, and the road was so narrow in places that Mr. Gill was frequently obliged to get a pole to pry the wagon hubs off the trees.”

The next day, Sunday, they arrived in Penetanguishene, but their journey wasn’t over yet. The road to the British base wasn’t completed and the penultimate part of the trip had to be completed as it began — in a boat.

Back to the Packet: “Next morning they were taken across the bay to the mouth of the stream on which the mill was built and taken in an ox-cart to the house just a week from one home to the other.”

Their possessions — travelling in another bateau — caught up to them within a week after their arrival.

At the mill, Jacob Gill had to adapt methods he’d learned for smaller trees in order to deal with the monstrous trees that were being cut at the mill. Too long and too thick to fit in the mill, the trees were hauled by ox teams from the shore to prepared saw pits, allowing one man to stand on the trunk and a man in the pit below to work the long hand saws, “each alternately pulling the saw up and down.”

Gill also acted as the bookkeeper and paymaster for his crews. In the winter, he returned with his family to Newmarket. The trip by sleigh over snow was much faster — only three-and-a-half days.

In the spring of 1832, Gill was ordered to Orillia to manage the construction of homes for newly settled First Nations. His family arrived a month later, travelling through Holland Landing and staying in the same place they’d stayed previously as they waited for the schooner, but this time heading north to Orillia, which was a day’s travel from Holland Landing. Gill had his mail delivered to Penetanguishene and it would then be sent by Commissary Department soldiers to his home in Orillia.

Gill was kept busy, building mills in Marchmont and George Copeland’s mill in Penetanguishene, not far from the original mill Gill had built earlier. Copeland’s mill was constructed almost entirely out of wood, with little metal — including gears and other works formed from local wood. He has a number of other key mills to his credit across the county, including the Hillsdale or Rumble Mill in Hillsdale, which was still in use into the 1960s.

Gill settled in Coldwater and died in 1846. He left an indelible mark on Simcoe County, having constructed a series of mills across the county’s sparsely populated and heavily timbered northern district and even improving one of the county’s key transport routes — the Nine Mile Portage.

Tom Villemaire is a former editor of papers in Simcoe County, including the Orillia Packet & Times, Midland Free Press, Barrie Examiner, Innisfil Examiner and Enterprise-Bulletin, and is the author of two history books. He now runs, podcasts and can be reached at