Yet somehow, despite the general tendency to squareness in political boundaries, electoral boundaries wind up with bizarre shapes...
Switzerland gets a honorary mention - the country might not be, but the people are total squares.
And back on topic, Switzerland's Wanderweg paths are numerous, very well signposted with bright yellow signs, and excellently maintained as well as clearly described in numerous guidebooks. Walking the countryside in Switzerland is a joy.
They might be! https://www.nytimes.com/2022/03/15/arts/alps-map-glacier-roc...
Or if your territory is made up partially of land the ownership of which isn't a pressing concern for anyone because it doesn't support a population and has few resources.
The western part of the boundary between U.S. and Canada is unusually straight, but I suppose that was an expedient agreement at a time when neither side wanted to go to war over it. Not that relations were totally peaceful or friendly.