Sometimes they can be challenging or overgrown, so you have to know what you're doing and be prepared to turn back if necessary, but I owe a lot of truly incredible experiences to this app.
Since it uses OpenStreetMap you should consider updating it for others later. Don't think you can do it in Organic, but it can be as simple as in a browser adding a note to a trail about what state it is in.
Just a small gif (as png didn't exist/widely supported) that had the rounded corner. Then if someone wanted to change the color or background you would have to redo all the images. Fun fun.