Windsor

01 / Why it matters

Why Windsor matters

Windsor sits across the Detroit River from Detroit, on the south bank, and it's Canada's southernmost major city. Statistically it isn't part of Metro Detroit, since U.S. metro areas stop at the border, but Detroit–Windsor is North America's most populous cross-border urban area, and Windsor is the other half of the border region. The Ambassador Bridge (1929), the Detroit–Windsor Tunnel (1930) and, since July 27, 2026, the Gordie Howe International Bridge tie the two cities together.

The riverfront parks run about 5 kilometers from the Ambassador Bridge to the Hiram Walker distillery, with terrific views of the Detroit skyline, and you walk among the pieces of the Windsor Sculpture Park on the way. Windsor is the Automotive Capital of Canada, Canadian Club whisky has been made here since 1858, and during Prohibition rum-running across the river to Detroit was big business.

Its history is tangled up with Detroit's. French farmers settled here in 1749, making it the oldest continuously inhabited European-founded settlement in Canada west of Montreal. In the 1800s it was a major destination on the Underground Railroad, and many freedom seekers who crossed the Detroit River settled in Essex County. If you're heading over, bring a passport; the Canada Border Services Agency recommends it.