The first signal that the change of industrialisation would touch Oakville Harbour was the incorporation of the London and Gore Railroad Company in March, 1834. The company was formed "for the purpose of constructing a... railroad or way commencing at the town of London... extending to the Harbour in Burlington Bay at the head of Lake Ontario [and then later to Toronto via Oakville]". 1 Although the plans fell through the first sign it was only twenty more years before the railways came to Trafalgar Township. The railroad bypassed the centre of Oakville near the mouth of the Sixteen in part because George K. Chisholm asked for an exorbitant $50,000 for the privilege. Instead it ran north of the boundary of Oakville near to Dundas St.. On Dec 3, 1855 the first train passed through the area causing great excitement. Thereafter six trains a day, three eastbound and three westbound, passed north of Oakville. It made the journey from Toronto to Oakville in thirty-eight minutes, and the fare was the same as by steamer or stage. 2

With the opening of the Great Western Railway from Niagara Falls to Hamilton in 1855 and to Toronto through Oakville in 1856, the steamboat interest suffered badly and "during the subsequent financial crisis in 1857, many lake steamers were laid up." The long time, efficient passenger service had been "diverted from the water, and the piers at most ports like Oakville gradually fell into disrepair". 3 The population of over two thousand at the time of the town's encorporation, fell to 14,50 by 1861. 4 For the next forty years, steamer service to Oakville was sporadic. Ships continued to carry passengers and freight between the larger ports like Hamilton and Toronto. However, most of the harbours in the smaller ports were neglected and too run down to accommodate steamers, and local traffic was not worth the effort the steamliners took. 5 By 1871 no steam vessels were built in Oakville; only four sailing ships were built and no barges. 6

In the wake of the passing of large-scale shipping, a resort town developed in Oakville in the 1850s and into the 1870s. Oakville was a "favourite resort for excursionists, who come by steamer from Toronto and Hamilton to spend a few hours" with its "facilities for boating." The Illustrated Historical Atlas of Halton County predicted in 1877, that "it will grow to be the great summer resort of Canada". 7

In September 1857, the Royal Canadian Yacht Club, formed in 1854, ran a yacht race from Toronto to Oakville for the first time. 8 This was the beginning of a whole new industry, interest and era in the town's history--that of the yachts. Yachting increased in popularity in the 1860s and, by the turn of the century, Oakville was often the destination for the Royal Canadian Yacht Club races during which, at times, fifty or more ships were seen in the harbour.

One prominent yacht builder, James Andrew, a native of Dundonald, Scotland, came as a youth to work on the lakes. By 1861 he was engaged in shipbuilding, building schooners on "the shores of many waters, gaining a reputation for swift-sailing ships". 9 When demand went down for sailing ships he turned to tugs and small steamers. Eventually he set himself up in a shipyard on the west bank of the Sixteen Mile Creek next to Doty's sawmill. His first ship, the Aggie, was christened in Oct., 1887. 10

The lakecraft which were launched into the waters of the Sixteen in the late nineteenth and early twentieth centuries were for a completely opposite purpose than those of the earlier days when shipping was paramount. Captain Andrew built racing and pleasure yachts for wealthy private citizens with no interest in the business of the lakes, only a strong interest in pleasure craft and pleasure sailing. As a result, the emphasis in shipbuilding had shifted from "weight, durability, and capacity," to "lightness of construction for speed". 11 The ships were fewer in number, but their fine craftsmanship and renowned performance gained them a reputation as some of the best built anywhere on the Great Lakes. Oakville was chosen as the destination of many Royal Canadian Yacht Club races including the Canada's Cup.

The Canada, one of Capt. Andrew's ships launched on June 23rd, 1896, was built from planking made of white oak drawn up from the river bottom at Dundas and the 6th Line, the site of the chute used to send staves down the river in the 1840s. 12 Andrew had been "given charge of the construction, had prepared all the material," and, because he had received, in advance, an early design of how the lead keel was supposed to look, he cast it ahead of time and the ship was completed ahead of schedule. 13 The Canada, skippered by Aemilius Jarvis, raced against the Vencedor from Chicago in August of that year. It won by over twenty minutes in a race between Toronto and Oakville. 14 In honour of the first winner of what would become an annual event, the race was named the Canada's Cup. In the next few years Jarvis would win only once more, in 1901, and lose in 1899, 1903, and 1907 in the Adele.

Andrew built several more yachts over the next twenty years including: The Minota and the Beaver in 1898-99, the Stratacona in 1902-03 and the Temeraire in 1904. 15 He was not alone in his pursuit of yacht building. Frederic Nicholls also built yachts at Oakville including the Crusader in 1907. Later there was an Oakville Yacht Building Company in the 1920s. 16

By the Depression yacht building and construction were on the wane. With less money and pleasure time, there was less of a desire for the products of the shipyards. One by one the yacht builders closed down or moved on to other activities. As of today there is only one yacht designer by the name of Mark Ellis left in Oakville. Though the yacht era in Oakville harbour was of short duration, the industry helped bridge the distance between the business and pleasure aspects of shipbuilding, and flourished in the time that Oakville was known as the cottage region of Ontario.


Brimacombe, Philip, The Story of Oakville Harbour, Cheltenham ON: Boston Mills Press, 1975
Canada Census, 1870-71, Ottawa: I.B. Taylor, 1876
Mathews, Hazel C., Oakville and the Sixteen: The History of an Ontario Port, Toronto: University of Toronto Press, 1953
Pope, J. H., Illustrated historical atlas of the county of Halton, Ont., compiled and drawn from official plans and special surveys Toronto, Walker & Mills, 1877
Smith, Russell D., "The Early Years of the Great Western Railway, 1833-1857," in Ontario Historical Society Journal, Vol. LX, #4, Dec., 1968 pp. 205-227


  1. Russell D. Smith, "The Early Years of the Great Western Railway, 1833-1857," (in Ontario Historical Society Journal, Vol. LX, #4, Dec., 1968 pp. 205-227) p. 205
  2. Hazel C. Mathews, Oakville and the Sixteen: The History of an Ontario Port, (Toronto: University of Toronto Press, 1952) pp. 198-199
  3. Philip Brimacombe, The Story of Oakville Harbour (Cheltenham Ont.: Boston Mills Press, 1975)
  4. Hazel C. Mathews, Oakville and the Sixteen: The History of an Ontario Port, p. 348
  5. Philip Brimacombe, The Story of Oakville Harbour
  6. Canada Census, 1870-71, (Ottawa: I.B. Taylor, 1876, Vols. 3), pp. 3-5, 226-227
  7. J. H. Pope, Illustrated historical atlas of the county of Halton, Ont., compiled and drawn from official plans and special surveys, (Toronto, Walker & Mills, 1877) p. 32
  8. Hazel C. Mathews, Oakville and the Sixteen: The History of an Ontario Port, p. 234
  9. Ibid., pp. 438-439
  10. Ibid., pp. 438-439
  11. Ibid.
  12. Ibid.
  13. C.H.J. Snider, Annals of the Royal Canadian Yacht Club: 1852-1937, (Toronto: Rous and Mann Ltd., 1937) p. 277
  14. Ibid., p. 275
  15. Ibid., pp. 280, 286, 290
  16. Ibid., pp. 295, 301