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I'm running into troubles planning a city ahead, because you don't get highways until 2600 population, and by that time, I kind of just expand into the area where I wanted my highway to be. At first, I thought I'd run it underneath the city, but after a couple failed planning attempts, I learned that I need to dezone the way. Can I lay down a one-way road ahead of time, and then upgrade it to a highway later?

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Yes, as HorusKol says, you can simply upgrade them by using the "!" button (in amongst "straight", "curved" and "freeform").

However, when laying out the city, take special care to leave space around the roads you plan to upgrade, and don't attempt any close/tight intersections. The 3-lane highway is quite a bit wider than a 2-lane road, and this will have 1 of 3 effects when you upgrade:

  • Demolishable things like ordinary buildings or power lines will light up in orange when you hover over the section, and will be demolished when you click. Make a pass afterward to fix any broken power lines or pedestrian paths (especially underpasses).
  • Un-demolishable things like roads and buildings that you paid to build (e.g. fire stations) will glow red when you hover. You cannot upgrade until you relocate or manually demolish all of these.
  • Sometimes, road intersections will not like the change, will glow red and prevent the upgrade. Usually, you can fire up the bulldozer, demolish the conflicting roads, do the upgrade, and then re-connect the other roads. Sometimes it just doesn't work.
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    Just like in real life, once a city has grown into its road system, it's hard to upgrade it!
    – Paul Z
    Mar 6 at 16:12
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Any road can be upgraded (or downgraded) to any other road - including highways - as long as you have the money and have the new road type unlocked

Bear in mind that any buildings on a non-highway road will lose their road connection, and any zoned tiles will also dezone, when you upgrade to a highway.

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