The river does not care which side you’re on. That’s the first thing I realize as I walk the Windsor waterfront, looking across the slow churn of the Detroit River toward the jagged skyline of Motor City. The water just moves—indifferent, unbothered by borders, carrying the same current past casino towers and crumbling warehouses, past sleek condominiums and derelict lots, touching both nations like a whispered secret.
Windsor is a city that often goes unnoticed. A shadow twin to Detroit, quieter, smaller, less storied. But shadows can be instructive. They show you the shape of things. And here on this stretch of Ontario’s southern edge—the southernmost city in Canada, which feels like it ought to be a punchline but isn’t—I feel that contrast keenly.
I expected steel and smog, I suppose. Windsor has long been Canada’s automotive heart, its fortunes rising and falling with the gears of the industry. Ford has roots here, deep ones. So does Chrysler. But as I stroll past the manicured parks along the river, past sculpture gardens and war memorials and families on bicycles, I find something else. Something softer. A city trying to remember itself beyond what it once built.
The story goes back farther than the factories, of course. The French settled here first, back in 1749, calling it La Petite Côte. The British came later, after the American Revolution pushed Loyalists north across the river. They brought with them loyalty to crown and order—but also rumblings of rebellion that would brew into the Upper Canada Rebellion. One of its leaders, François Baby, has a house here still—now a museum—and I think about how strange it is to walk the same streets as those who once debated whether this land should remain British, become American, or try something altogether new.
Windsor was once called Sandwich, which is somehow perfect. A name caught between two pieces of bread, or in this case, two empires. And like any good sandwich, Windsor is layered: Indigenous roots, French fur trade, British redcoats, Underground Railroad stops, 20th-century labor strikes. It has been a crossing and a refuge, a battleground and a border town.
During Prohibition, it flourished—not by law but by loophole. Detroit went dry and Windsor got wet, supplying bootleggers with Canadian whiskey and becoming a backdoor to sin. Al Capone’s men walked these streets, not with menace, but with money. Even the churches looked the other way, I imagine, if the offering plate was full.
Now, the riverfront is quiet. Two lovers sit on a bench with their backs to Canada, gazing out at the towers of another country. I wonder what they’re thinking. Do they dream of escape? Of something bigger? Or are they just content to sit, knowing the crossing is always there if they need it?
Windsor doesn’t demand your attention. It doesn’t throw its history at you like a parade. But it rewards those who linger. Those who ask: What does it mean to be a border town? To always be next to something louder? Windsor is the pause between verses. The breath before reply. And sometimes, that silence says more than anything else.