That particular tracking thing is something I've been using to create an overlay map for my Garmin Edge 800. But it also has its uses on my computer as a tool for seeing places I needed to go. Even without having a GPS it could be useful for keeping track of where you've been. I made a setup guide for it a while back. The basic process is to download your local road network, and delete the stuff you have ridden. A lot of manual editing at the start if you already covered many roads. https://www.dropbox.com/s/vg1ir955nz9xb8u/Unvisited%20Road%20Garmin%20Overlay.pdf?dl=0
Since I do a bunch of OpenStreetMap editing I just used some of the free programs available for that. The JOSM editor will easily display hundreds of gps traces at once so you can prune out the roads you already covered. Whenever I'd do a new ride I'd just load the gps trace and delete some more roads. The program supports a variety of background maps including OSM and Bing satellite.
There is a website now that does the matching using data from Strava, which is probably good enough for most people and requires no effort. Depending how your local paths and roads were mapped on OSM, some won't be included for matching, as the site excludes service roads and footways. http://wandrer.earth
Strava's Personal Heatmaps (a paid feature) are another way to track city coverage. http://www.jonathanokeeffe.com/strava/map.php
does something similar using Strava data but is less permanent, they cache your rides for a while but I'm not sure how long.
If planning to use gps traces and want functionality similarish to the above 2 options, I also put together a guide for creating an offline gps database that displays all your gps traces at once. One thing I like about that program is that it lets you create very high resolution images. https://www.dropbox.com/s/lngmjuwmp4u4lwa/GPS%20Map%20Database%20with%20QGIS.pdf?dl=0