I don’t know if you’ve been asked this before, but what would you think of a city being built around Winterfell? A map Roose Bolton looked at in S5 showed all major roadways in the North were connected by it, and LOIAF showed that a tributary of the the White Knife ends near it (and WOIAF states pirates used to use this river to raid the heart of the North near Winterfell, suggesting it is entirely navigable).

There sort of is one already, the winter town, which has a population of ~50,000 in autumn and winter, and ~10,000 in spring and summer. 

So you wouldn’t need to build a city, just expand the existing town. 

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