After my last group ride I discovered I could use a GPS. I already have a TomTom One with RAM mount and I was determined to make it work how I needed. There's no waypoint adder to this device, and the new TomTom Routes program dosn't support Waypoints either, so I downloaded Tyre. This program is a little slow, but it works perfectly.
Unrelated to this, I did have to hack the One to open up Itinerary Planning, but that's another story. After I unlocked this feature I was able to access the loaded maps I created in Tyre. Just make sure you put every waypoint you think you'll need because the TomTom will configure its own quick route between waypoints if you're not specific.