Here’s how I plot out a potential walk before I go, sometimes: I use CityStride’s map pathing.

Other times, of course, I just wing it. But I’ve been bit by missing a block mid-neighborhood in places before and my sense of completionism drives me to go back, so this helps.

I’m also not completing every citystride “segment” so I ignore that mechanic - it includes a few alleys which aren’t actually open to the public and paths that don’t exist anymore.