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So there's something I've always wondered about KW for a long time. As you probably know, our local road system is confusing. There's some sensibility to the way they're laid out in Cambridge, but once you cross over into Kitchener or Waterloo, things get loopy. Weber and King intersect each other multiple times and roads curve off to nowhere and change names, such as Fairway and Courtland. That's only the beginning. Anyways, how did KW's road system evolve into what it is today? Does anyone know enough about KW history to explain this?
I have one guess, which stems from the fact that Kitchener doesn't have an inner-city expressway. Many North American cities had expressways pushed through their downtown areas, but I can see that Kitchener resisted this. It appears as if the southern part of the Conestoga Parkway forms what looks like a partial ring road around what would've been the existing urban area at the time it was built. Perhaps roads were oriented in strange directions so that connectivity to the highway was maximized.
I would guess that many of the roads are very old and were there before things were built up. Some may have belonged to different municipalities and each may have had a different name for the road. Then there's geography: rivers and hills. It's much the same around Dundas/Ancaster/Aldershot/Hamilton. Old roads like Kings St. in Hamilton wind all over, just like Weber/King in KW. If you really want to get lost, go to Brantford.
Furthermore, addresses along King Street in Waterloo are designated as being either North or South, while addresses along King Street in Kitchener are designated as being either East or West, but on the map it is all one long road. This was done actually to reduce confusion in addresses between the cities.
It was the early German settlers that didn't find a need for a grid-system. When you think of it, our road system has some advantages and disadvantages.
Advantages: Roads in KW lead everywhere
Disadvantages: Planning bus routes, development.