That works if the route line is straight, but if the route doubles back on itself the wipe might reveal the end as it reveals the begining, sort of thing.
you could do the animation in Flash or similar software, and export as .AVI so you can import it into an editing package.
I had a go at doing something similar in Premiere 6 using a Track Matte, (which I didn't have a clue about until I read this thread).
The result should be attached as a wmv file, my first attempt at using a matte, needs a bit of work, I basically followed the instructions in the thread above and the Premiere Help file. (if it's helpful I can go through exactly what I did)
I'm not sure what software you have, but it should be possible to do in most decent packages I guess.
There are probably better ways to do it, but the best software for it is a good editing app, or an animation program like Flash, and if you know what your doing and want professional results try After Effects or something.
Panasonic SD9, Panasonic NVGS-75, Canon MV600i