Pioneer Travel Aboard the Fly

Pioneer travel aboard the Fly describes the value of sailing vessel as a connection between a pioneer settlement, survival, and the outside world. The Fly would prove to be a valuable asset to the early settlers of the community that would become Owen Sound.

In the 1840s Owen Sound's first settlers realized the importance of their watery connection to the outside world.


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One of the first settlers, W. C. Boyd, purchased a fifteen-ton vessel, the Fly, to transport his family and supplies to what is now Owen Sound. Although Boyd was mainly interested in building a home and commercial establishments in the wilderness, he realized that the Fly was important as a means of communications with the outside world. 

pioneer travel on boyds flyW.C. Boyd Owner of the Fly

Boyd, or his crew sailed the Fly to places such as Detroit, Coldwater, and Goderich either to sell produce from the Owen Sound region or to pick up the supplies necessary to sustain the pioneer settlement at the base of the Bruce Peninsula.

The only other commercial vessel known to ply these waters in 1842 was a schooner named the Wanderer, under the command of a Captain Borland.

Captain Borland periodically visited Owen Sound to trade for produce. But with that lone exception, early Owen Sounders had to rely on the Fly, foot travel, or horseback to reach the outside world.

Pioneer Travel on Georgian Bay
Could be Dangerous

As many know, the waters of Georgian Bay can be very dangerous, especially when the weather takes a turn for the worse.

The memoirs of pioneer travel on the area waterways by an early citizen of Owen Sound, A.M. Stephens, provides us with lurid details of some of the dangers faced by the Fly, and those who sailed her.     

In the summer of 1842, Boyd dispatched Stephens, Isaiah Chokee, who maintained the Fly for Boyd, and acted as cook on sailing ventures, and another settler named MacNab, to pick up wheat at St. Vincent and then continue to Coldwater to have the wheat ground as there was not as yet a mill in the village of Owen Sound.

Continuing on About Pioneer Travel Aboard the Fly

As the Fly left St. Vincent and headed into the gap in the Christian Islands shortly before sunset, the wind began to pick up.

As the sun went down, lightning lit the sky. As the storm began to intensify MacNab and Isaiah went below to turn in for the night. Stephens became concerned about the severity of the storm and he called to MacNab for assistance in shortening the sails.

However, when MacNab poked his head out of the companion hatch he stated that he "thought there would be more noise than wool, as the devil said when he shaved the pig". 

Before MacNab had time to turn in, the storm struck with all its fury. With all the canvas still up, the schooner was thrown on her beam ends. Fortunately, the vessel had been under full headway, she was able to right herself.

Stephens described what happened next. "With the night as dark as pitch, the rain coming down in torrents, the sea making a clean sweep over us, the wind howling, the thunder roaring and the lightning flashing, I can scarcely be laughed at for wishing myself safe on shore. It was a nice position for two land lubbers such as MacNab and myself to find ourselves in."

With MacNab at the helm, Stephens and Isaiah scrambled to shorten the sail. As Isaiah loosened the flying-jib it slipped out his hands and when he tried to catch it the block struck him on the head knocking him flat on the deck. 

Stephens stated "...if my head had received such a blow I think the storm would have troubled me no longer". However, Isaiah scrambled to his feet and secured the sheet and stowed the jib.

Once all the sails were under close reef they were obliged to stand off and wait the storm out until morning. Stephens described the damage they found once the light of morning arrived. "We found, lying on the deck one of the jaws of the main gaff, full of long spikes, which had been wrenched off by the gale. The foremast was broken off close to the deck, and held in place by the stays and shrouds only.

Considering the violence of the storm and fact of its striking us with all sail set, the wonder is that either the deck was not swept clean, or the ship sent to the bottom with sails, spars and rigging, hands, cargo and cook."   

Despite the damage done by the storm, the Fly continued to Coldwater, where the wheat was ground and brought back to Owen Sound.

Later the same summer Boyd asked Stephens to take the Fly to St. Vincent for another load of wheat.

With the same crew they headed out. Upon passing the Vail's school, a storm arose. Although they were new to pioneer travel, they were not inexperienced about the power of Georgian Bay storms.

Not wishing to experience a repeat of the earlier storm Stephens, MacNab and Isaiah stowed all the canvas except the foresail which was close-reefed and close-hauled and lashed the helm hard down, and all retired below to ride the storm out.

When the crew awakened in the morning the storm was over and the schooner had not sustained any damage.  However, much to the surprise of the crew the storm had carried them a considerable distance past Cape Croker. Fortunately, they missed drifting onto Griffiths Island or the Cape.

The rest of the trip to St. Vincent and Coldwater was uneventful.

No More Pioneer Travel
on Georgian Bay for Boyd

In the winter of 1842-43 Boyd sold the Fly to Captain Alexander MacGregor and his son. This transaction marked the beginning of the long career of the MacGregor family as sailors in the Georgian Bay region.

But the impact of the treacherous waters of the region would still affect Boyd's commercial ventures and himself personally.

In the fall of 1843, Boyd sailed on board the schooner St. Joseph, with a load of potash and fish for market in Toronto.

After passing through the channel at Tobermory they headed south along the Lake Huron shore of the Bruce Peninsula. 

As they approached Southampton a violent storm came up and drove them off course. They were forced to seek shelter in the lee of Chantry Island. They dropped anchor and set about to ride out the storm.

Unfortunately, it soon became evident that the storm was so intense that their place of refuge could not protect them or their vessel from the winds and the waves. In addition, the anchor failed to obtain a grasp on the stony bottom, and they found themselves drifting precariously towards the breakers where they would either be swept overboard or frozen to death in the water while clinging to the certain to be overturned St. Joseph.

As pioneer travel in the waters of this region was new to them, Boyd and the crew guessed that they should be near to the mouth of the Saugeen River. As the night was dark as pitch, visibility was extremely poor.

However, the foam on the crest of the breakers stretched like a white band along the shoreline. Fortunately for Boyd's group, a break in this ribbon of white was clearly noticeable in the distance. They surmised, that this gap might indeed be the mouth of the Saugeen River. Having nothing to lose, they lifted the anchor and sailed into the abyss which they hoped would bring safety in the form of the much calmer sheltered waters of the Saugeen.

Their guess was correct and there they waited out the storm.

That adventure was Boyd's last, as far as is known about his pioneer travel, on the waters of the Bruce Peninsula region.


For more tales of pioneer travel aboard the Fly, and on land routes on foot and with ox carts, and many other stories about the early days in the Owen Sound region of Georgian Bay check out my book Owen Sound: the Port City.

Georgian Bay Shipping

List of Lighthouses on the Great Lakes: If you have names and/or pictures of Great Lakes Lighthouses please submit them along with details of their location.

Georgian Bay Ships: A List of all the ships that sailed on Georgian Bay until the 1960s. This list is not complete. If you know of a ship that sailed the waters of Georgian Bay please contact me with information about that vessel, and, if you have a picture that I could post with it, that would be much appreciated.

1885: A Memorable Summer Job for Owen Sound teenage boys on the Great Lakes would have historic importance, not mention a possible exciting career opportunity.

Hindman Transportation Company was a well-known Great Lakes shipping company for many years. Here you will find pictures of many of the Hindman ships

Owen Sound Harbour – A Photographic History, by Robert A. Cotton is a book that interests my historiographical curiosity.

Commercial Great Lakes Fishing  It is probably safe to suggest that the commercial fishing industry was an important part of the early growth of this region.

A Georgian Bay fishing vacation has long been a popular attraction in the Bruce Peninsula region. During fishing derbies, the regional waterways are dotted with fishing boats of all shapes and sizes. 

The Georgian Bay Mackinaw, designed by William Watts of Collingwood is an example of a Georgian Bay innovator creating a vessel to service the needs local mariners.

Great Lakes fishing is an asset that is protected and developed, not only for its economic potential but also for those who just enjoy spending a day by the side of a river or in small fishing boats trying to catch “the big one”!  

Great Lakes Fishing History is not without its controversy. The impact of the fishing industry was such that it played an important role in the development of communities along the Georgian Bay and Lake Huron shoreline.

Georgian Bay Travel Before the Winter Freeze-Up could be a dangerous time for mariners in the early years in this region.

A Harbinger of Spring on the Great Lakes in pioneer times, was the eagerly awaited news that a lighthouse had been lit and shipping traffic could begin sailing from port to port.

Lumber Hookers  Lumber hookers and tugs were an important innovation to improve the transportation of lumber on Georgian Bay. 

Mapmakers on Georgian Bay were also explorers. They mapped the Georgina Bay shoreline noting safe harbours, dangerous reefs and other guides for sailors and pioneer settlers looking for a place to call home.

Paddling Georgian Bay & Pondering: traversing parts of this great waterway in a canoe leads one to wonder about the ships of a bygone era battling the rough seas they encountered.

Parry Sound Shipping History: The Parry Sound area has always been connected to the southern regions of the Province of Ontario by a system of good roads. Or has it?

Parry Sound’s shipping history 2 is more than the tragic sinking of the Waubuno or the later catastrophe surrounding the sinking of the Asia. 

Sailing Season Closing: A Frantic Time on Peninsula as ships raced from port to port delivering and picking up passengers and produce before the waterways froze.

Ship Captain Andrew Port was not only a dynamic and brave Georgian Bay mariner, he was a personal favourite historical character of mine.

Ships Stuck in Ice: The Oak Glen was icebound in 1996 but this sailing hazard has been impacting vessels on Georgian Bay since the beginning of time.

Lake Huron shipwrecks, the Hibou often occurred in the Georgian Bay region of that Great Lake due to the often violent waters that could strike unsuspecting vessels like the Hibou.

Shipwrecks: The "Asia" wrecked off the eastern coast of Georgian Bay taking all but two of the more than 100 passengers to a watery grave.

Masters, Mates, and Pilots Association created its first Canadian chapter on Georgian Bay, providing maritime safety education, and other seafaring issues to better inform its membership.

Pioneer Travel Aboard the Fly  Tells the story of a sailing vessel as the tenuous link between survival and death in a pioneer settlement in the 1840's in Upper Canada.

Sailing Stories: the Captain Who Smelled his way into Port The Captain Who Smelled his Way into Port details how pioneer seamen on Georgian Bay safely sailed the rough waters without the aid of the modern technological tools so readily used by today's mariners.

Sailing Story: The Voyage of the Prince Alfred the incredible voyage of the Prince Alfred, fraught with danger for both vessel and the crew in the winter of 1880.

Shipbuilding As the southern Georgian Bay region became more populated shipping traffic increased to meet the needs of an expanding market place.

The Summer of 1844 was No Picnic for the early settlers in the pioneer area near what would become Owen Sound on Georgian Bay.

The CPR Grain Elevator Fire of 1911 spelled the end of Owen Sound's role as the eastern terminus of the CPR Great Lakes Fleet.

Georgian Bay shipping occurred long before the first Europeans paddled these waters. But the fur and timber trades opened Georgian Bay to shipping in a big way! 

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  2. Georgian Bay Shipping
  3. Pioneer Travel Aboard the Fly

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