I'll admit, I don't have the best track record in this area. But on the whole I'm a respectful interloper, staying to the edge of property lines when the woodland trail I'm on suddenly leads me right into an alien backyard.
One of my solutions is to determine if a house looks currently habited. If owners are out of town, they won't mind if I walk up their long driveway instead of staying longer on the busy thoroughfare. Now, of course, no one is out of town.
On yesterday's walk I suddenly found myself in a ferned forest with muddy paths and the only way out (rather than back) being along the side yard of a yellow split-foyer. I just squeaked by on that one, seeing the owner out with a mower only 10 minutes after I'd skirted his lawn.
It was a close call for this trespasser.