My Magellan will do this with the software it came with.
One program I use, but never see anyone reference is USA Photomaps.
http://jdmcox.com/ It will display your routes, tracks, and waypoints over Photos, or Topo maps downloaded from terraserver. It will do this automatically, and save the images on your hard drive. I don't recommend it for dial-up users though. Best of all, it's free, but he does ask for a donation.
Give it a try, If you don't like it, at least you aren't out anything, and you can delete it.