AddMagMap is a shareware program that allows you to add custom objects to Magellan MapSend maps - trails, roads, lakes, etc., such as the addition of the Appalachian Trail shown at right.
The program also allows for the import of shapefiles and custom Garmin maps, such as those found at MapCenter.
AddMagMap differs from MobileMapper Office (covered in my book - GPS Mapping), which allows you to create custom maps for magellan receivers from scratch. Any of these solutions are probably best suited for the technically inclined. The website does a pretty good job of explaining things, though the creator's English is a little rough around the edges.
A couple of threads on Groundspeak and the Yahoo! eXplorist group may help inform things before you jump in.
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