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What we call York Region today follows the same concession “grid” for the most part, so the old Township of York, did it have a defined northern boundary at what we now call Steeles?

As Township of Markham having clearly a continuation of York’s concession survey, why in their right mind would they skip 4 whole concessions?

Concessions are a different animal than numbered streets, I like to think of the concessions as being more similar to the Mile Roads in Metro Detroit. In that the roads in question are far apart.
Present day York Region is an amalgam of several historic townships making up York County which, at one time included much of what is now Toronto. Most were surveyed using the 'Concession Grid System' running east and west from Yonge St. ; although if you look at the attached image from Wiki, it appears that Scarborough and Georgia used a different reference. A 'concession' is a surveyed parcel of land that was fronted by a road allowance, typically numbered away from the front or baseline. The land was further broken into blocks by road allowances running perpendicular to the concession road, typically called 'sideroads' or 'sidelines', These were also numbered, although often using Roman Numerals. The standard of measurement was the 'chain' which was 66 feet (hence why a typical road allowance is one chain). The most common block of concession subdivision was 100 chains (1 1/4 miles) although that could vary.

Everything was numbered because it was a legal, land allocation system, not a social system. Besides, how many people could read and write back then. Naming became more common as areas became urbanized. As well, the 911 numbering system necessitated some roads to be named to avoid duplication. In this sense, "16th Ave." is name; although it is also numbered as Regional Rd. 73.

In some cases, as settlement spread out along development roads, they often just surveyed a corridor on both sides of the road, with later surveys further off the corridor being completely different.

1675000672820.png
 
Queen Street (formerly Lot Street) is in what was the Township of York.

16th Avenue in Markham is part of a different township: the Township of Markham.

Different townships have different concession reckonings.

For Markham, 1st Line is Yonge Street, 2nd Line is Bayview Avenue and so on until 12th Line, which is the York-Durham Line. 13th Avenue is also known as Steeles Avenue, there's 14th Avenue, there's 15th Avenue (also known as Highway 7), then there's 16th Avenue, then there's 17th Avenue (also known as Major Mackenzie Drive), then there's 18th Avenue (also known as Elgin Mills Road), then 19th Avenue, then finally 20th Avenue (also known as Stouffville Road).

For Toronto (specifically the part that was formerly York Township), Queen Street is the first concession, Bloor Street is the second, St. Clair Avenue is the third, Eglinton Avenue is the fourth and so on with Steeles Avenue being the 9th concession.

Yes, Steeles Avenue was both the 9th Concession (going by York Township reckoning) and 13th Avenue (going by Township of Markham reckoning).
The layout of York Township isn't precisely correct.

From Queen Street to Eglinton Avenue there are three concessions, called "from the Bay", and their concession roads are Queen Street, Bloor Street, and St Clair Avenue.

North of Eglinton, York Twp switches to concessions running north-south, with Yonge Street at the centre; the concession roads are:
- Weston Road (only adheres to the right of way north of Sheppard Avenue)
- Jane Street
- Keele Street
- Dufferin Street
- Bathurst Street
- Yonge Street
- Bayview Avenue
- Leslie Street (deviates quite a lot between Eglinton and Lawrence)
- Woodbine Avenue (now occupied by the Don Valley Parkway north of Lawrence)

(South of Eglinton many of the above streets divide lots in the "from the Bay" concessions.)

If you google "ontario make a topographic map" you'll find this awesome GIS that shows Ontario's cadastral structure: https://www.lioapplications.lrc.gov...ewer=Make_A_Topographic_Map.MATM&locale=en-CA
 
Not sure if this belongs here, it can be moved if necessary.

Anyways, I’m aware that 16th Avenue derives from the Concession Road system, where in York County’s case, concessions were drawn 100 chains or 1.25 miles apart. This makes sense for the naming conventions of both 14th Avenue and 19th Avenue.

Obviously, Queen (formerly Lot Street many years ago) is the first concession, yet by the position of 16th Avenue, Queen should be 5th Avenue. What gives? It’s something I’ve always wanted to know.
Did you ever get a reply to why Markham's avenues start at 14? Like you I've tried different ways of counting and can't come up to 14, and it doesn't reflect Markham Township's concession/lot fabric.
 
Did you ever get a reply to why Markham's avenues start at 14? Like you I've tried different ways of counting and can't come up to 14, and it doesn't reflect Markham Township's concession/lot fabric.

The numbering sequence doesn't come from counting the concession roads north from Queen, it comes from the system where after the numbering of north-south roads reached the old Markham Township's eastern limit at the 12th Concession (York-Durham Line) the numbering continued as east-west "Avenues" starting at 13th (Steeles Ave.).
 
The numbering sequence doesn't come from counting the concession roads north from Queen, it comes from the system where after the numbering of north-south roads reached the old Markham Township's eastern limit at the 12th Concession (York-Durham Line) the numbering continued as east-west "Avenues" starting at 13th (Steeles Ave.).
Thanks, that sounds plausible (if a tad weird IMO). Do you have a reference for it?
 

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