Are you sure you have a map installed on Mapsource? It should definitely be able to plot a route between two checkpoints. You may need to add extra way points to get it to follow a particular set of roads if you don't like what it initially suggests.
Google Maps will do it although it takes some work (as does Mapsource) but if you're planning on running it on a Garmin GPS then you'll need to use Mapsource or Basecamp.
I've got no idea how to run Google Maps on a phone as I use a GPS.
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