Country Roads, Take Me Home

A checkerboard of roads should make navigation straightforward, but in Headwaters, survey quirks, naming oddities and nature’s whims can challenge both drivers and GPS apps.

March 14, 2026 | | Country Living 101

A drive on the country roads of Headwaters can be a great adventure – or an exercise in frustration. Still, finding your way around should be easy. Theoretically.

Head (more or less) north or south in most of Headwaters and you’re (probably) on a concession road or line; head (more or less) east or west and you’re (probably) on a sideroad. Check the line and sideroad number at the next intersection, and you can (probably) figure out exactly where you are. Sounds straightforward, right? But there are gaps – sometimes huge gaps – between theory and practice.

The reasons for these gaps are historical, geographical and, inevitably, political. The first surveys of Ontario started in the late 18th century, when the plan was to divide the province into a tidy grid of townships, each roughly six miles square. But by the time most of Headwaters was surveyed in 1819–20, this plan had fallen by the wayside.

One reason was the geography of Headwaters, which created challenges for surveyors. Swamps, steep hills, deep valleys and rivers often got in the way. Imagine coming upon the Niagara Escarpment while bushwhacking through virgin forest with an axe, a 66-foot chain and a compass. No wonder the work of one surveyor didn’t always line up with that of another. This explains the  frequent jogs in country roads and why some roads end abruptly before continuing on the other side of a natural feature.

rural maps
Illustration by Ruth Ann Pearce

The curvature of the earth also affected surveyors’ measurements, so the grid needed to be reset every few miles. Then there’s timing. Ten years or more would often pass between the survey and settlement, making the surveyor’s markers hard to find – and road allowances sometimes a matter of guesswork.

Still, townships continued to be divided into tracts called “concessions” because the Crown would “concede” (grant or sell) lots within the concessions to settlers, who were required to clear the land, erect a dwelling, and build and maintain the roads.

And concessions were numbered, though the numbering system varied. Road allowances, called “concession roads” or “lines” usually established the eastern and western boundaries of each concession. In much of Headwaters, these lines run north-northwestward (or south-southeastward, depending on your perspective), and the line that marks the eastern boundary of each concession takes the concession number. So, for example, drivers on a First Line of a township will usually know that they are on the east side of the First Concession.

Lots were also numbered, usually from south to north, and allowances for cross roads or sideroads that run (more or less) eastward–westward were established at specific intervals between lots. In much of Headwaters, the interval was every five lots. So in Erin, for example, 5 Sideroad runs between Lots 5 and 6, 10 Sideroad runs between Lots 10 and 11, and so on.

But the direction of the grids varied. Lines in Caledon and Erin, for example, are oriented more sharply northwestward–southeastward than those in most of Dufferin County. And even in Dufferin, there are variations. In East Garafraxa and most (but not all) of Melancthon, the alignment of lines is similar to that of Caledon and Erin.

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  • For early surveyors, Hurontario Street (known south of Orangeville today as Highway 10) became the centre line for the grid of concessions in Chinguacousy, Caledon, Mono and Mulmur townships, though in Mulmur, it’s known as Centre Road. Envisioned as an essential link between Port Credit on Lake Ontario and Collingwood on Lake Huron (hence the portmanteau name), this street never entirely lived up to the government’s original grand plan. Still, its slight changes of direction as it was pushed northward through the bush dictated the alignment of the concessions in the townships it passed through.

    Hurontario Street also influenced the numbering of the concessions in these townships. In Mulmur, for example, concession roads are named First Line E or First Line W to specify whether a line is east or west of Centre Road. In Mono, the initialisms EHS (East of Hurontario St.) and WHS (West of Hurontario St.) fulfill the same purpose.

    Historically, EHS and WHS were also used in Chinguacousy and Caledon. But in 1974, when the provincial government folded the townships of Caledon, Albion and the northern part of Chinguacousy into the newly created Town of Caledon, residents were suddenly faced with, for example, five Fourth Lines: one in the former Albion Township, and two in each of the former Chinguacousy and Caledon townships, both of which included a Fourth Line EHS and WHS.

    Not only did this befuddle drivers, but it also created challenges for emergency services. The solution? Dispense with the former numbering systems and assign names such as Mountainview Road and Shaws Creek Road. And so a remnant of history was lost.

    Even for residents, the variation in the grids that make up Headwaters can be confusing. For visitors and the growing number of delivery drivers, it can be downright baffling. 

    About the Author

    Tony Reynolds is a freelance writer who lives happily above Broadway in Orangeville. More by Tony Reynolds

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