Delorme maps will do that. Not automatically perse, by you can enter your start and end insert vias and stops and it will draw your route. We use it for planning then add updates as the route changes, and it always does. I save a separate file set for we ach trip, sometimes a separate fi l e for eave direction,.
You can also add notes and other graphics to record your plans or to document your trip highlights.
It is Windows based (possibly Apple too].