I'm not really sure if this is what Miii was trying to say? But I tried to add some lines of where I thought a path might work and then read back over Miii's post and I think most of its similar. It's kinda hard to plan a path this way in my opinion, though
I have to make a gridded map of my towns in MS Paint to really plan things out (which doesn't take nearly as long as it seems).
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Here's a gridded map for my town Lorhaven that I've been working on a lot lately, just as an example.
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This way I can just go in and change ideas up as I think of new ones or if things don't end up working out in my town like I want c:
Like originally I wanted there to be a second bridge going directly down below the bridge under my mayor's home, on the left side of the map. But Isabelle wouldn't let me put one there >.< so I had to replan lol.