The last few years I've been using Strava to find new places to ride (looking where other people like to ride) and keeping track of where I haven't been yet (empty spots on heatmap).
A few years back using the heatmap and my Edge 800 map display I set out to ride the entire city a chunk at a time. And since last year I've expanded my exploring to the multitude of unpaved roads surrounding the city.
Made the video with this:
http://renderfast.com/runparticles/ and Cam Studio screen recorder from about 80 rides covering 4,000 km.