Hi djtentman,

to Laptop GPS World.
Microsoft Streets and Trips has always been quite good at doing route optimization. It is a very simple procedure. All that a user needs to do is to enter all your stops, decide which one is the start and which one is your destination, and then press the "Optimize" button. It will reorder the stops so you can get from start to finish in the shortest time (or shortest distance, which ever your preference).
The current version, Streets & Trips 2010, is capable of exporting to Garmin personal navigation devices, and it is also able to export GPX files. But I haven't personally tested this functionality, so I do not know how well it would work in real life. This export feature is new to S&T, and I haven't yet heard much user feedback on it.