Source data is mostly from the Cleveland Critical Mass blog and everyone who has contributed GPS traces & route maps, especially Shawn Mariani, Will Skora, and Josef Arvidsson.
GDAL::OGR and GPSBabel (thanks for the tip, Will Skora!) were used to reshape the data, and Tilemill and Mapbox to build, style, and host the map. The Tilemill project for this map is on Github, (where the map's custom styling is defined).
This site runs on Drupal, which is also delivering ride destinations to TileMill. Code for this site is on Github, too.
Mucha inspiración from Tom Macwright's running map and the Global Adaptation Institute's RunKeeper track in DC.
I build websites -- and other stuff like apps and maps -- as Substrate Websoft. Find me, also, on Facebook or Twitter.
+ Jeff Schuler