Hi Charles: I've recommended this guidebook to a number of other posters in this Q&A forum, so forgive me if I sound like a stuck record, but I think you should check out Jamie Jensen's "Road Trip USA" guidebook (available on Amazon here: http://www.amazon.com/Road-Trip-USA-Cross-Country-Adventures/dp/1566917662, plus his website also contains a ton of other useful info: http://www.roadtripusa.com/). One of the cross-country routes he highlights is called the Oregon Trail and covers the route from New York to Oregon and taking in such highlights as Mount Rushmore and the South Dakota Black Hills, Yellowstone National Park, and Oregon's Columbia River Gorge. Sounds like it might fit the bill for your trip! Here's some more info: http://www.roadtripusa.com/routes/oregontrail/oregontrail.html