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It may feel like Chicago to be here, but it will feel a lot like Boston during the Big Dig to drive here, at least downtown.
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We apologize for the construction/road work/general whatever. Actually, we apologize a lot, but these things deserve it.
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We are going through a phase of trying to accommodate bike riders physically as well as legally, so be ready for bizarre forms of bike lanes. (And if Torontonians in general are perceived as entitled, believe me: the Toronto bike riders take it to a different level.)
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So do the Toronto pedestrians.
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Toronto has streetcars, which are electrically powered things bigger than a city bus that travel on rails in the middle of several downtown streets. If you're beside one and it wants to stop for passengers, you are required to stop behind its rear doors. Be sure to do this, even if it's impossible.
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We do have a few amusing geographical things, like a street called "Avenue Road" and another street called Dundas that follows one of the primal trail routes instead of the grid pattern and therefore manages to intersect two subway lines that are at right angles to each other.