Woodstock was first settled in 1800 after Sir John Graves Simcoe, governor of Upper Canada, determined that the area would make a good site for new community. The early settlers were generally American immigrants from New York State.
In 1836 there were 200 people living in Woodstock, and by 1844 the population had grown to almost 1,000 inhabitants and nearly 200 homes. Woodstock was incorporated as a town in 1851 and had its first town meeting in the Royal Pavilion Hotel. This year also saw the start of the Town Hall and local government.
In 1901, Woodstock, now with a population of almost 9,000, asked the provincial legislature for city status and the “Town of Woodstock" was incorporated into the "City of Woodstock".
From 1900 to 1920, an electric train ran down the streets of Woodstock; as well, after 1920, bricks were used to pave the main street of Woodstock. The bricks were later removed in the 1940s.
In 1979 Woodstock suffered damage from a series of tornadoes, but everything has since been rebuilt and restored.