Is this really a winning analogy? To let everybody bumble along until patterns appear seems like a myspace strategy. Another option is to put up fences. And set folks on a finite number of paths. And call it facebook.
Leaving your app - using the trail analogy - as an open, untamed field may not be the best way to go, but I don't think any app would survive by setting up rigid fences and refusing to adapt them as they apparently become obsolete.