You COULD walk from Ashland to Jacksonville now, but either on the shoulder of a busy road, or by bushwhacking through the wild (or both).
But an alternative is in the works: the Jack-Ash Trail is planned for the ridgetops between the two communities. Work could start later this year.
The trail has the backing of Luke Ruediger, devotee of all things related to the Siskiyou Crest, and a blogger about his efforts and interests. He and a companion plan to hike the trail route soon; he drops by to talk about trails, timber, and other issues in the Siskiyous.