Simcoe County history

By Tom Villemaire, Special to Postmedia Network

Spring isn’t far off, and with the arrival of spring, cottage season will soon follow – and Simcoe County is the gateway to cottage country for much of Ontario.

It was an Orillia merchant and businessman who helped build and foster the cottage industry not just in Simcoe County, but also in the surrounding areas. Not only that, but Alexander Peter Cockburn helped build the main communication routes – water, railroad and road – in northern Simcoe County and Muskoka and on the east coast of Georgian Bay.

Cockburn was born in eastern Ontario’s Stormont County in 1837 to Scottish immigrants. At the age of 20, he’d moved with his family and was working at his father’s general store in Kirkfield. He opened his own store in Kirkfield at the age of 26, and became the postmaster. He was soon trying his hand at politics and served as reeve in Victoria County’s Eldon Township before moving to Orillia in 1864.

In Orillia, he set up his own business, The Montreal, a dry-goods operation that brought the big city to the county town. He met, and later married, Mary Helen Proctor of Beaverton, just down the shore of Lake Simcoe. Proctor’s family had loads of business connections around Lake Simcoe that would help Cockburn when he made his next move.

That move was inspired during a fall vacation in 1865, when Cockburn took a canoe trip in Muskoka. He paddled Lake of Bays, Peninsula Lake, Fairy Lake and Lake Vernon and the Magnetawan River, completing the trip with an overland hike to Gravenhurst. Gravenhurst was then a pioneer settlement and Cockburn was charmed. The locals introduced him to Lake Muskoka, which he loved for the scenery and the businessman in him loved for the potential. Timber, tourists and sportsmen – Cockburn was transformed into the biggest proponent of the near north.

Back in Orillia, he met with area businesspeople and, like a zealot, he expounded on the potentials of northern Simcoe County and nearby Muskoka. He published a pamphlet to help broadcast his views on the many advantages of the territory on the front porch of Orillia.

(He might have gone too far when he suggested it was good farm country. But everything else seemed to hold true.)

The next year, Cockburn built one of Gravenhurst’s biggest businesses with the construction of a large store, loosely modelled on his Orillia operation but with an eye to also recognizing the locals were in need of less glam and more modest items. He established a stagecoach connecting the Lake Couchiching-Lake Simcoe steamers with the Muskoka lakes at Washago. On Lake Muskoka, he built his own steamer, the Wenonah. Offering reliable transport for people and cargo and mail around the lake, this boat was loved by the locals. He even catered to early loggers, hauling small booms of logs to mills with the craft.

Cockburn was back in politics in 1867, representing the area including the Muskoka lakes. He lobbied for lock construction at Port Carling and a canal at Port Sandfield, giving steamers – and the passengers and cargo they carried – access to Lake Rosseau and Lake Joseph. He helped encourage people to make the area home by convincing the Liberal government to pass the Free Grants and Homestead Act of 1868. He also founded the Muskoka Settlers Association and was made its president.

He linked Simcoe County’s major city, Barrie, to Muskoka by pushing for the North Simcoe Railway to build a line from Barrie to Gravenhurst, which was finished in 1875.

All of this gave average folk in southern Ontario cheap and ready access to north Simcoe County and Muskoka land and lakes not just for vacations, but weekends as well.

By 1905, Cockburn had a fleet of steamers, plying the lakes of Georgian Bay, Muskoka and Simcoe County. His steamers stopped in Barrie, Georgina, Collingwood, Orillia, Washago, Midland, Penetanguishene, Port McNicoll, Victoria Harbour, Parry Sound, Huntsville and elsewhere, not to mention covering Lake Nipissing for a time as well.

You may even recognize one of the steamers. The RMS Segwun was built on the remains of a discarded steamer called the Nipissing, which was a sidewheeler. The Segwun is still in operation and is the oldest steamer in North America.

His operations would have some contact with virtually every piece of mail, store item and even passenger in the region.

Cockburn’s company even created the most spectacular resort: the Royal Muskoka Hotel. Located on Wrenshall’s Point, Lake Rosseau, it was designed by Lucius Boomer, the same man behind New York City’s Waldorf Astoria. Construction began in 1901.

Cockburn did come to regret that his efforts to open the area to the south of the province caused a logging explosion. Cockburn had fallen in love with the view and the wildlife. He recognized the money the timber represented, but he didn’t like the desolation it left, and it remained a sore point with him even as his family members grew rich from exploiting the forests.

He had a village named after him at the far end of Lake Joseph, where stagecoaches running to North Bay would pick up travellers at the steamer dock. When the rail neglected to connect in 1906, the village slowly died.

Cockburn fell in love with the Canadian Shield and the lakes and forests that covered it in northern Simcoe County and Muskoka, and wanted as many people as possible to share it. William H. Pratt of New York City was inspired by Cockburn and opened the Rosseau House resort on Lake Rosseau in 1870. In 1900, the local paper called Cockburn “the Father of the Muskoka Tourist Industry.”

When Cockburn died in 1905, the Royal Muskoka Hotel, owned by his company, was considered the finest facility in the area. Sadly, the giant on the lake succumbed to fire a half-century after it was built. Cockburn’s landmark in the area remains in the tens of thousands of cottagers, millions of tourists who spend hundreds of millions of dollars in the region. His contribution was recognized last year with the dedication of the town square in Gravenhurst in his name.

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