In the early 1900's the Independent Order of Foresters or I.O.F. chose Oakville as the location for their orphans' home. It was located at 53 Bond Street. The home was part of their plan to care for children of deceased members.
It later became the "Ortona Barracks", the headquarters of the Canadian Army in World War II. It is presently the Oaklands Regional Centre, a school and home for the developmentally handicapped.
In 1805, all the lands on the northern shore of Lake Ontario between Etobicoke and Hamilton, except the land situated at the mouths of Twelve Mile Creek and Sixteen Mile Creek, were purchased by the Assembly of Upper Canada from the Mississauga Indians.
The detail in this photograph is amazing. You can see the old Central School (the current library location), the old Radial Bridge (now Rebecca Street), etc.
Take a look at some old pictures of the Hamilton Radial Railway that used to run from Oakville to Hamilton and see how it looks today.