Long trips, how long would the drive take you?

When we visit to Massachusetts, we generally take 4 to 5 weeks each way. There is so much to see. On drive days we like to start out about 10:00 and stop by 3:00. When we do a layover, depending on what we choose to see, we plan 3 to 5 nights. If we are just driving, we like to do 1 night then 2 nights. I would consider the Michigan UP as well as the Soo. Also lakes region of Minnesota, House on the rocks and Taliesin in Wisconsin, Teddy Roosevelt Park in ND, Black hills in SD.