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Most cities don't just spring into existence, they aren't planned to be the way they are (there are a few exceptions, see Milton Keynes in England for example) but grow organically over time. However when you're building a world, you're designing cities that have existed for hundreds, if not thousands of years or longer.

How do you ensure your city feels organic in nature, that it doesn't appear planned an built in a day as it probably was?

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    $\begingroup$ Ever play Sim City? It just turns out that way. $\endgroup$ – JDługosz Nov 22 '15 at 4:37
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Simulate it. :)

Naturally I don't mean some highly detailed computer simulation.

I mean sit down with a pen and paper and follow the process through.

Founding

Why was it first founded here? What was the purpose of the settlement? Why choose this location? Most settlements are founded for a reason. For example London is where it is because it was the lowest crossing point on the Thames. Other cities grow up around easily defensible areas or other strategic objectives.

Growth

Sketch out the early stages of the city. Would they build walls or other structures, how would it grow inside? Take into account natural features that might change the shape of the city, for example important buildings would tend to be on high ground.

Events

What happens? What notable events have happened to the city? Has it been invaded? Grown? Plague? See with each ones what changes it might make to the structure of the city.

Expansion

As the city expands it grows outside the walls, then more walls form are built around the expansion. Is it remodeled or changed in the process? Where do the people live? Do they grow outwards or upwards?

Think about how each area might change. Where would the rich people move, where would the poor people be able to afford? Would areas decay or be built up? How do goods get in and out of the city, and get transported around, etc?

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    $\begingroup$ To expand: cities can be founded from trade outposts, military installations, geographic phenomena, and probably most commonly from sites of abundant natural resources (coasts, verdant areas, mineral deposits). A very common city changing event is a large scale fire. Many older large cities have large fires as major events in their histories. The older the city, the more likely that concentric shapes of walls are found. Newer cities instead will have older buildings versus new developments. $\endgroup$ – Attackfarm Sep 17 '14 at 0:38
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    $\begingroup$ Great answer! +1. The topography of the area should also be considered. Will the logical next expansion of the settlement be onto the swamp to the west or the flat plain to the east? Where are there rocky outcrops, crevice and other "hard-to-build-on" types of terrain located? These will most likely be the last places the settlement will spread to, (although unofficially, this might not be 100% true. Consider favellas). $\endgroup$ – Cal West Sep 17 '14 at 8:35
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    $\begingroup$ Don’t forget the fusion of smaller nearby cities into a larger entity and the big city annexing smaller ones. Some towns have several centers due to this, while others grew in rings like a tree and have just one central downtown. Also remember that often the name gives away the reason for original foundation (e.g. -ford ‘river crossing’). $\endgroup$ – Crissov Nov 9 '15 at 12:00
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The best way is to grab a bunch of maps (both cartographical and descriptive) and pictures of cities in the real world that share similarities. Then you can figure out reasonable trends and aspects for your target environment/history. Sure there may be no directly comparable cities but just go for the closest you can find.

One important thing to do when going from real maps is: unless you want it to appear based on a real city make sure that it has significant enough differences. For example mix and match some aspects and definitely include some unique elements. One good test is get a few friends to read it and ask them if it makes them think of one place - if they all say the same place (and this isn't their home-town) you may have more similarity than you want.

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    $\begingroup$ To expand l this idea, I would also use Google Streetview, or a similar technology. Search for images, both historical and present day, of that comparable city, too. Along with the maps, you could get a sense of which areas are older, which areas are renovated, which areas are new, which are mostly abandoned in terms of development. $\endgroup$ – Attackfarm Sep 16 '14 at 19:25
  • $\begingroup$ I would say that streetview is too close for anything bigger than a hamlet but Google maps would definitely be one of my preferred tools $\endgroup$ – Nick Wilde Sep 16 '14 at 19:29
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    $\begingroup$ A map won't show you the specifics the questioner is wanting. Unless you personally know the city, a map can't offer which buildings are "historic", which buildings are built over an older part of the city, and which buildings are newly developed. That natural progression needs either a detailed historical set of maps (which aren't common) or a more detailed view of the streets, buildings, and land. $\endgroup$ – Attackfarm Sep 16 '14 at 19:48
  • $\begingroup$ I suppose it is true that driving maps are generally next to useless for that purpose but with a careful eye you can make some good generalizations - and if you overlay a satelite view you can see make a fairly good analysis. Most towns (at least in North America) have tourist info centres many of which have historical maps - those maps in combination with more modern maps can be really useful. $\endgroup$ – Nick Wilde Sep 16 '14 at 20:36

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