Woodstock , is also known as the Dairy Capital of Canada, or The Friendly City. In 1792, Sir John Graves Simcoe became Lieutenant Governor of Upper Canada and for the next five years, made plans for the development of the interior of Upper Canada. After visiting the area the following year he envisioned a series of villages linked by a military road and a system of rivers and canals, providing inland access during an era when commerce and settlements depended on major waterways. These communities and roadways also provided an overland supply route for the safe movement of troops and settlers.
Although designated a potential town site in 1798, Woodstock was not settled until 1800, when two Americans, Zacharias Burtch and Levi Luddington applied for land grants. Zacharias and his sons cleared 12.5 hectares (30 acres) and built the first log house along Dundas Street, on the present site of the Woodstock YMCA. The Burtches were joined by other American settlers who purchased land south of Dundas Street.
These American settlers dominated the political and commercial structure of the developing village causing provincial leaders to question the loyalty of this emerging community. The area was subsequently settled by a large population of English and Scottish settlers, as well as naval and military officers loyal to the crown.
The Woodstock City Hall, now a museum was designed after the town hall in Woodstock England. The Bell Tower of Old St. Paul’s Anglican Church served as a jail during the Mackenzie Rebellion of 1837.
Vansittart Avenue (named after Admiral Henry Vansittart, an early settler) in Woodstock's west end has one of the finest residential Victorian streetscapes in the province.
In June 2005, Toyota, the world's second largest automaker, announced plans to build a new, $800 million automobile assembly plant in Woodstock on a 1,000-acre (4 km²) undeveloped site in the city's northeast end.
Woodstock Raceway has harness racing once a week from June til September. A farmer’s market is held every Saturday on the fairgrounds. The fairgrounds are also the site of the Woodstock Wood Show usually held the first weekend in Oct. and is reputed to be the largest of it’s kind in North America. Housed in the Town Hall is the Woodstock Museum. Eight galleries tell the story of Woodstock from 10,000 BC to the present.