Prior to European exploration and settlement, the Windsor area was inhabited by Canada’s indigenous peoples and Native Americans. Windsor was settled by the French in 1749 as an agricultural settlement. It is the oldest continually inhabited European settlement in Canada west of Montreal.
Windsor's French Canadian heritage is reflected in many French street names, such as Ouellette, Pelissier, François, Pierre, Langlois, Marentette, and Lauzon. There is a significant French-speaking minority in Windsor and the surrounding area, particularly in the Lakeshore, Tecumseh and LaSalle areas.
In 1794, after the American Revolution, the settlement of Sandwich was founded. It was later renamed Windsor, after the town in Berkshire, England. Located on Windsor's west side, the Sandwich neighbourhood is home to some of the oldest buildings in the city. Windsor was the site of the Battle of Windsor during the Upper Canada Rebellion in 1838.
Windsor was established as a village in 1854 (the same year the village was connected to the rest of Canada by the Grand Trunk Railway/Canadian National Railway), became a town in 1858, then gained city status in 1892.
During the 1920s alcohol prohibition was enforced in Michigan, while alcohol was legal in Ontario. Rum-running in Windsor was a common practice during that time. Also during the 1900s, Windsor had success as a railway centre, and made notable contributions to World War I and World War II fighting efforts.