Cooksville was home to the Clair House vineyard and the Canada Vine Growers Association between 1864 and c1926, which was the first commercial winery in Ontario.

 

Cooksville was home to a renowned Master Baker, Henry Fullwood, between 1917 and 1956. He was famous for his soufflé and baked goods, and his products shipped internationally. In 1923 he won a gold medal for his Fullwood Fruit Cake in an exhibition in London, England. His bakery was known as the Model Bakery.

 

Cooksville was originally known as Harrisville after its first settler, Daniel Harris. In 1836 the community adopted the name of Cooksville, after Jacob Cook, one of the area’s industrious and leading citizens.

 

Cooksville was swept by fire on May 26, 1852. The fire started in Belcher’s Blacksmith shop and forge. Little of the village survived. The fire consumed 35 houses and businesses, 16 barns and 4 stables. The former Copeland General Store on the southeast corner of Hurontario Street and Dundas Street was built in 1852 following the fire.

 

The Agricultural Fall Fair was established in 1836 and ran during the first or second weekend in September until 1858, when it began to alternate annually with Streetsville. The fairs featured sport competitions, horse shows and racing, an auction, fruit stands and a famous bicycle race. When Streetsville no longer wished to “share the fair”, Cooksville formed their own fair committee in 1897. The last Cooksville Agricultural Fall Fair was held in 1951.

 

Confederation Parkway was originally called Hook Avenue named after Edward James Hook, who subdivided the property, and at first only ran south of Dundas Street. For a short time it was known as Royal Windsor, before being named Confederation Avenue in 1967, in honour of the centennial of Canada’s Confederation. At that time, a new public square was unveiled in front of Town Hall, called Confederation Square. In 1969 it was renamed Confederation Parkway, and in the late 1970s and early 1980s the road was extended north of Dundas Street.