Actually, there are a couple of companies who have accurate topographic mapping programs instead of having to buy separate paper maps but getting all the ones you need can be pretty expensive (but way cheaper than buying all the paper USGS maps).
Delorme has a topo map program but I have "TOPO!" and it has excellent detail but only for California and it was about $50. Each state or set of states is another about-the-same cost. It is also not that easy-to-use, but I use it for 10-70 mile backpacking trips. Long driving trips planning with it would be a lot of work.
If you don't need EXACT details you can purchase Trailer Life's Directory Campground Navigator 2009 (I have 2008). This allows you to plan or plot your trip and after getting the "Directions" and creating waypoints, each waypoint will post the highest elevation for the segment. The program is affordable, not THAT easy to use, but will get the job done. It is VERY RV/Camping specific but a good program for what we do. Unlike other travel plotting programs elevation is important because it is geared to RVers who need to know grades and roads not good for rigs.
If you need more information on these feel free to email or PM me. I have had experience with Delorme's Map-n-GO & Street Atlas, Microsoft's Streets and Trips, and several other mapping programs because I am a nut about planning trips with great detail.
Good luck and happy plotting.
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