DID YOU KNOW: St. Paul Street is Hiding a Rare "Boston Secret" in Plain Sight? 🇨🇦

A rendition of the unique curves of St. Paul Street.

I’ve lived all over Niagara and driven down St. Paul Street more times than I can count, and I never thought twice about it. I’ve also hung out in cities like Boston, MA where winding streets are everywhere! But here in Ontario, a "curved" downtown is almost unheard of. It turns out, while every other city was being forced into a straight grid, St. Paul Street was busy following a mind of its own...

 

The Road That Refused to Be Straight

 

Most of our local streets were drawn by surveyors using a ruler to create perfect squares. St. Paul Street is a rare exception because it wasn't "built"—it was inherited from an ancient Indigenous trail. This natural path existed long before the city was a hub for the Welland Canal, serving as a vital link across the region. While cities like Boston are world-renowned for their tangled, "cow-path" layouts that date back centuries, Ontario’s landscape was almost entirely flattened into a rigid, predictable grid. St. Paul Street remains one of the few places in the province where history simply refused to be straightened out by a surveyor’s pen.

Fast Facts:

• • Original Route: Part of the Iroquois Trail spanning 50 km (31 miles).*
• • The Curve: Follows the lower ridge of the Niagara Escarpment.
• • Rarity: One of the only major downtown main streets in Ontario that isn't a straight line.
• • Heritage: Central to the St. Catharines Heritage Conservation District.

*While the entire Iroquois Trail stretched for hundreds of kilometres across Ontario and into the States, the section that became our local Highway 8 (connecting Queenston through St. Catharines) is the part roughly 50 km (31 miles) long that most locals identify with.

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SOFISTIKATEIT VISUAL ARCHIVE

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"St. Paul Street in St. Catharines" — Visual by Mike R. Duncan

Surprising Secrets

• The Ancient Ridge: The street curves because it stays on the natural high ground of the Niagara Escarpment, allowing early travellers to avoid the swampy lowlands of Twelve Mile Creek.
• The "Un-Planned" Path: Early settlers simply built their shops along the existing winding trail instead of straightening it out to a grid.
• Indigenous Heritage: The route was originally a major Indigenous trail connecting the Niagara River at Queenston to the head of Lake Ontario.
• The Boston Connection: While organic growth like this is common in older cities like Boston, the strict British surveying of Ontario makes this downtown layout a rare engineering "accident."

Source(s): St. Catharines Downtown Association | St. Catharines Museum Blog