Hot Rod Power Tour! Seven cities in seven days. Thousands of cars, back road America.
We traveled about 2600 miles and a blast, met a lot of great car folks as well.
That would top my list, although I would prefer to stop over in moderately-sized towns, (up to 75,000 population) rather than cities. Problem is, these tours all take place back east. It would be cool to organize a power tour of the northwest, (WA, OR, ID, WY, MT and BC) where we have it all; huge mountains, tall trees, unspoiled coastline, farmlands, orchards and high, dry deserts. I can think of some great back roads, scenic stopovers and and towns to consider. I would prefer keeping a NW event much smaller than the "thousands" they draw back east, perhaps only a few hundred.
Potential Stopovers: Port Angeles WA, Astoria/Lincoln City/Newport, OR; Grants Pass/Ashland, OR; Bend, OR; Pendleton/Baker City, OR; Idaho Falls, ID; Jackson, WY; Bozeman/Livingston, MT; Anaconda, MT; Missoula, MT; Couer d' Alene, ID; Walla Walla, WA; Wenatchee, WA; Penticton, BC; Harrison Hot Springs, BC; Whistler, BC and Victoria, BC. This would be a sampler of some of the best scenery in the NW, while avoiding the larger population centers along the I-5, I-84 and I-90 corridors.