Windsor was first settled in 1748 as a French agricultural settlement, making it the oldest continually inhabited city in Canada west of the Quebec border. The area grew out of a small Jesuit Mission and was first named Petite Côte (Little Coast), and later became known as La Côte de Misère (Poverty Coast) because of the sandy soils near LaSalle.

These French roots can still be seen in the pattern of roads and streets in the downtown area being elongated, this reflects the French method of agricultural land division where the farms were long and narrow, fronting along the river. You’ll also find that many street names are French, such as:

• Ouellette
• Pelissier
• Marentette
• Lauzon

There is a significant French speaking minority in Windsor and the surrounding areas. Many of them are in the Lakeshore area.

In 1794, after the American Revolution, the settlement of Sandwich was founded. It was later renamed to Windsor, after the town in Berkshire, England. The Sandwich neighbourhood on Windsor's west side is home to the oldest buildings in the city including Mackenzie Hall, originally built as the Essex County courthouse in 1855. Today, this building functions as a community centre. The oldest building in the city is the Duff-Baby House built in 1798..

Windsor grew in steady unison with the city of Detroit, MI on the opposite bank of the river. The settlement grew slowly and remained under French control until 1797, when an increasing number of British loyalists began moving in, seeking to remain under British rule and avoid the political changes of post civil war America.

Windsor is also the final stop of the Underground Railroad and the history is preserved at the John Freeman Walls Historic Site

The town of Windsor changed further with the arrival of Great Western Railway in 1854, in what is now Downtown Windsor. This move ensured commercial success for years to come, connecting the township with the larger centers in the north.

In 1904, the Ford Motor Company set up shop in Windsor, beginning what would become the area’s most prominent industry. So big was the automotive industry that during the First World War the growing industrial complex was actually known as Ford City.

By 1930, the industry had become so influential that Windsor had grown to include the smaller surrounding communities into a city of 100,000 people. The Second World War led to further increase in both industrial production and growth of the city.

Today the city of Windsor is still primarily a manufacturing based economy, remaining a forerunner in automotive engineering. The Windsor region is also eastern Canada’s largest agricultural business community. This, combined with an ideal location and more than 800 companies in the Windsor area, secured an impressive 40% of the Canada-USA trade market, generating an exchange of $400 million dollars daily between the two countries.