For what it's worth, I've been picking up some GIS skills lately. Here's a proof-of-concept I made. I need to find a better background image, and I need to add the rest of my data (a few thousand files spanning three or four years), then categorize and color code it. But this includes a few of the more interesting rides.
If anyone wants to do the same thing with their data, I used MapWindow GIS (free and open source) and got the background here:
http://webgis.wr.usgs.gov/globalgis/datasets.htm