Get my kicks on RT.66. Get back to the Lower St. Lawrence River in May/June.
Cool idea and what will you be driving? Make it a motorcycle so you can afford Obama 4 dollar gas.
Since I have lived close to RT. 66 for the last 50 years I have a bit of advice. There are several guide books on how to travel the route. A lot of it does not exist anymore and so to really experience it you need to get a book.
A lot of people do not know the history of the route. It is fascinating. I recommend reading about the history as it also is a history of automobile travel in the US back in the 20's and 30's.
Another good book about a lot of the country it goes through, i.e., New Mexico, Arizona, and California is "A Tramp Across the Continent" by Charles F. Loomis. Fascinating travelogue and a fascinating character.
Have fun, time is short.