I would stay at least 2 days at John Day so you can explore the Fossil Beds, tour the old farm and do not miss Kam Wah Chung State Heritage Site. It is so interesting.
We are leaving as soon as we get our doctors appointments past and as its winter, making a beeline for Arizona and New Mexico. We plan to visit Organ Cactus Natl Monument, Tombstone, and Bisbee going east, and Navajo Natl Monument, Canyon De Chelly, and Monument Valley on the way home. In New Mexico, Gila Natl Monument, Silver City, and Calsbad Caverns going east and then we are going into Texas to spend some time at Big Bend. Homeward bound, we are going to visit Santa Fe and Taos Chaco Canyon. Most stops will be dry camping or boondocking and I just highlighted some of the more famous places.
If your a Good Sam Club member then have a trip planning site that gives tips on places to see and do along your route. I found it to be okay, but Google Maps works also.
Remember, its the journey Happy Travels
