My husband and I did it on our own, not an organized ride. The only safety issues were I didn't see a single car for the whole ride, so just carry your own supplies. I did feel the altitude, making it challenging but definitely doable and enjoyable. You could stay either in fort davis or Balmorehea. We stayed in one of the indoor lodgings at the Balmorehea state park we reserved through the website in the above link, mostly cuz our daughter's weekend event was centered there, and made day trips to fort davis. Lodgings were not fancy, but comfortable and adequate.