The Oakville Harbour and the Sixteen: by Bill Harris

The Sixteen and the Harbour attracts industry
William Chisholm purchased from the Crown the lands around Sixteen Mile Creek in 1827 for 1029 pounds. The costs of developing the harbour and his power company, The Oakville Hydraulic Company, forced him to borrow more money, and to mortgage the lots he had developed in the town.

Water powered our first industries. By 1851 there were 15 sawmills on Trafalgar Township streams. Five were on the Sixteen between Dundas Street and Lake Ontario. One of Oakville's first industries was William Chisholm's gristmill. Three stories high, built of river stone on the west bank of Sixteen Mile Creek, it was upgraded in 1855 with a flume and tunnel that led under the railroad tracks from a curve in the river below the cemetery. It continued to mill flour until 1930 when it burned down.

The Ships from Oakville Harbour
Water transport was necessary not only to ship the region's timber and grain, but also to move passengers. The two hour trip from York to Oakville by steamboat was much faster than the six-hour stagecoach trip and in most seasons, far more comfortable.  William Chisholm established Oakville's first shipyard on the south bank of Sixteen Mile Creek at the north end of Navy Street. The shipyard launched its first ship, the 50 ton, 80-foot, two-master schooner Trafalgar, in 1828, and its first steamer, the Constitution, in 1833.

For fifty years, wind-driven fleets carried freight from Oakville. Schooner after schooner left the harbour filled with squared pine timbers, oak staves, and wheat, returning with immigrants and merchandise.  A forest of masts extended from the lake to the Colborne (now Lakeshore) Street bridge. Grain warehouses lined the east bank. A lighthouse built at the end of the pier could be seen from 10 miles away.  Oakville reached the height of its shipping trade in the 1850s. It became an official Canadian Port of Entry, collecting duties on imports from the United States, with William Chisholm acting as customs agent. The coming of the railroad is 1855 meant that wheat and timber could be sipped to the larger harbours at Toronto and Hamilton. The harbour fell into disrepair, and was sold to the Town of Oakville in 1874 for $250.

Changing Times
By the 1870s Oakville was becoming a year-round resort town. In summer the hotels were filled to capacity, and hundreds more people arrived on day excursions via lake steamer. Tourists could rent canoes, rowboats and sailboats. The town's waterfront beach offered good swimming and fishing.  Beginning in the 1870s, sailing for pleasure and competition expanded greatly on Lake Ontario. Oakville became a destination for Royal Canadian Yacht Club races from Toronto. On summer weekends, fifty or more yachts were often tied up in the harbour.

Oakville's shipbuilders turned their attention to pleasure craft. One was Captain James Andrew, whose shipyard had been producing schooners and smaller commercial craft since 1861.  James Andrew's yacht the Canada, built in 1896, won the first Canada-USA match race for sailing yachts. The trophy, known since as the "Canada's Cup", is still competed for a hundred years later.  A refuge from the storms, and base for industry, a birthplace and home for many ships and a centre for recreation, that has been Oakville's Harbour Heritage in the years past. So much has changed. We can only be sure that in the future the harbour will continue to change.

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