The Early Village Information Station pavilion in George's Square contains panels that tell the story of the early village from 1806 to 1870. This information is reproduced below.
The area that is present day Oakville was first settled by Europeans in 1806, after the land was purchased from the Mississauga tribe and Trafalgar Township was surveyed. Twenty-one years later, in 1827, William Chisholm bought 960 acres at the mouth of Sixteen-Mile Creek, developed a harbour, and laid out the village of Oakville. As the village prospered and grew, roads and ships were built to connect it with the rest of Upper Canada. The arrival of the railroad in 1855 took business east and west by land rather than just north and south along Trafalgar Road to Lake Ontario. As rail traffic replaced shipping, Oakville's harbour declined. By 1871, the town's population had fallen by half, to 1000 people.
Trafalgar Township settlers lived in isolation during the early years. Travel was difficult, and there was no newspaper or postal service. But transportation and communication links were not long in coming. The first stage-coach service began along Dundas Street in the 1820s. By 1833 stage-coaches were also travelling along Lakeshore Road, and Oakville had regular steamship service to Hamilton and York.
Farmers north of Oakville needed a road to deliver their crops to Oakville's mills and harbour. In 1831 the House of Assembly provided funds for construction of the 7th Line, or Trafalgar Road. Fifteen years later this busy road was upgraded to a planked road, complete with toll gates. With postal service beginning in 1822, and a newspaper (the Oakville Observer) starting up in 1836, Oakville and Trafalgar Township's early years of isolation came to an end.
During the 1830s, Oakville entered a prosperous era. Shipments of wheat and lumber made the harbour a busy focus of commercial activity. Steamships and stagecoaches carried passengers, mail and freight to and from Hamilton and York. William Chisholm's 1835 town plan provided for a park at this location, to be named after his father George. Around George's Square and along Trafalgar Road, residents built substantial homes, many of which are still standing today. The village grew to 2000 residents by May 27 1857, when it was officially incorporated as a town.
As Oakville's population and prosperity increased, stately homes were built near George's Square. These houses represent different architectural styles and designs from various periods in the town's development.
The Underground Railroad secretly transported fugitive slaves from the southern United States across the border to freedom in Canada. From 1820 to 1865 thousands of black slaves escaped into Canada. Although Oakville was a small terminus for the Underground Railroad, hundreds of blacks came to this area. One was James Wesley Hill, who crossed the border in a packing box. Hill settled on a farm near Oakville and helped many slaves who followed by giving them work on his farm.
Relations between blacks and whites were mostly good in Oakville. Schools were integrated, church groups mingled and black employees worked in the town's businesses. For years, Oakville's black citizens celebrated Emancipation Day with an annual picnic in George's Square. Slavery was abolished in Canada in 1834.
Oakville's churches, schools and taverns knit the community together and created a social support network. Taverns and inns were usually the first public buildings in Upper Canadian towns. They doubled as town halls, churches and courthouses. Churches were built as soon as money could be raised. William Chisholm donated land to the Methodists and the Catholics for their churches. By 1840 Methodists, Catholics and Presbyterians all had chapels in Oakville. The first public school was established in the meeting house in 1836. The Oakville Common School was built in 1850. An addition to the building in 1854 allowed a grammar (high) school to be established as well.