When William Chisholm bought the land that surrounds the mouth of the Sixteen in 1827, there was a system, albeit incomplete, of roads in the area between the Town of York and the Town of Burlington. To accommodate the settlers and to join the communities, a road had been constructed several years before after the Mississauga Purchase through the region. Sandwiched as it was between the rapidly expanding York and Niagara Districts, the strip soon transported a large number of settlers to their destinations west of York. Some years later the settlement of the Niagara Middle Grand District (up to Burlington) and the York area (Etobicoke and east) began to grow together.1
The road system planned and begun by John Graves Simcoe was the first step in securing the western regions. Simcoe decided to build a military road from Burlington Bay to the Thames, near London, Ont., and then in the opposite direction to York.2 In the early summer of 1793, a contingent of the Queen's Rangers, companies of militiamen in a post Revolution capacity, was put to work building this road which was named Dundas Street.3 However, "in the matter of roads there was little progress to report in these years, or for some time afterward".4 Despite the matter of increasing population, the pattern of the dispersed settlement still made it difficult to provide a good system of local roads. District officials "lacked, or claimed they lacked, the financial resources to get on with the task, with the result that there was mounting pressure on the provincial legislature to assist in the building of purely local roads".5
Weekly stagecoaches began winter service in 1817 in the highly developed eastern portion of Upper Canada on the Kingston Road, taking from two to four days to make the trip between York and Kingston.6 By the 1820s similar stagecoach lines were run by various proprietors along the Dundas Street between York and Hamilton.7 In the late 1820s and into the next decade, stagecoach travel became somewhat faster service and continued all the year round. In the 1830s these provided, "by contemporary standards, a fairly comfortable trip in winter and in dry midsummer weather, although most travellers found it wise to take full advantage of the regular and frequent stops at taverns along the way".8 In 1833 Boyce's Telegraph Coach began running along the Lake Shore Road. By eliminating the travel time to the lake shore the trip took six hours from York to Oakville, and a similar time from Oakville to Hamilton. William Weller's Telegraph Line was also added in 1835. Their numbers remained generally the same until the 1850s when the service increased; despite the introduction of the Great Western Railway, the time had been reduced to five hours.9
Great changes were occurring within Trafalgar township during the 1830s as well. Settlement was moving many miles inland with the opening of the new townships to the north and the need for local roads to be improved became apparent. Oakville on the shore of Lake Ontario would have to be linked to more northern villages in Trafalgar. In 1831 the House of Assembly appropriated funds for a road from Post's Inn at the south-west corner of the 7th Line (now Trafalgar Road) and Dundas Street to Oakville.10 By the 1840s the traffic was such that the 7th Line was improved when the Trafalgar, Esquesing and Erin Road Company was established in 1846. They created a planked road that stretched sixty miles from Oakville to Fergus, Ont. Other planked roads were to follow, but they lasted only a few years before having to be replaced.11
Transportation was of primary importance, but, in addition, communication became increasingly important as the town grew. The township gained a post office when the Trafalgar Post Office opened in 1822 in Dundas, Ont. at Dundas Street and the 9th Line, followed by Nelson's at Hannahsville, northwest of Oakville, in 1825.12 Oakville's Post Office, when it was established in 1835, was a "bye [by?] route of the Trafalgar Post Office, mailbags being transported back and forth on horseback." The frame post office was on the east bank of the Sixteen on the south side of Colbourne Street, west of Navy Street.13 Shortly thereafter, the Oakville Observer was established on February 8, 1836.14 Journalism was a practice that was heretofore vastly more difficult due to the small trickle of information into the town. With the quicker movement of people into the town there was a constant stream of news to report from abroad. As was typical of the papers in the province of the time, the Observer would have concentrated mostly on external news because local news was passed quite efficiently through the town by word of mouth.
As far back as 1825 it was asserted that the Post Office system should be under the supervision of the provincial legislature rather than the government in London, England, a demand that "was periodically renewed over the next several years".15 Finally, a provincial take-over of mail service was effected, a practice which increased time with efficiency and harmony of service and prices. After 1855 the Great Western Railway took over the carrying of the mail. As a result, the train stopped in Oakville and the Oakville Post Office received Trafalgar and Bronte's mail instead of the reverse as it had in the past.16
The quality and quantity of postal service did improve steadily not only on the roads but also with the advent of steamboats on the Great Lakes after 1815.17 In and around 1833 regular transport started on land and also on the waters of the north shore of Lake Ontario.18 The steamer Constitution was built to provide steamer service to and from the head of the lake to the capital at York both for passengers and freight. The ship was launched at William Chisholm's shipyard on Jan 19, 1833. Since the lake steamers in the 1830s were "the only method of speedy travel, so their accommodation was in fullest use, and their earnings at the largest".19 Moreover there was one, the Chief Justice Robinson, which was the only steam-operated vessel in the Western end of Lake Ontario, equipped with "an ice breaking ram-style bow and thus she was able to keep the Oakville service operating all winter".20 Oakville's population was now connected to the towns in its region of Upper Canada as well as by links to larger cities like York, Kingston and Montreal. The transportation would be invaluable in the next twenty years when Oakville's industry would flourish.
Brimacombe, Philip, The Story of Oakville Harbour, Cheltenham ON: Boston Mills Press, 1975
Craig, Gerald M., Upper Canada, the Formative Years, 1784-1841, Toronto: McClelland & Stewart, 1963
Mathews, Hazel C., Oakville and the Sixteen: The History of an Ontario Port, Toronto: University of Toronto Press, 1953