If I’d have read that ealier 
Then I’d made a different picture than the ones below - taken right at the point of the transition - standing on a small bridge over a drain, one looking forwards, the other looking backwards, camera position nearly fix.
Note that both show a constructed path, there are sure-fire clues on the ground. There are guideposts at both ends. Under current regime the one in the woods should get excellent and the other might get anything ranging from good to no, depending on which clue gets applied. I am fairly certain, that according the SAC Hiking scale this will classify for mountain hiking.
Changes in appearance like this may have prompted dissolving visibility from difficulty in historic OSM times. It’s both easy hiking, isn’t it, technically? I have seen that too often: In situations like this, people will just head straight to the next visible road, even when that is much more inconvenient than walking where the terrain provides an easy way.