"Wonder what the time frame was? I can't imagine any casual hiker walking across Afghanistan this day and age"
Just after we invaded Afghanistan. As he neared Kabul, he almost got himself killed when he was traversing country where the Taliban were active. It is a very interesting read, as he took the road less travelled, north of the main road running from Herat to Kandahar to Kabul.
As for the "liberal, hedonistic.....trail", the hippies were merely tolerated because they paid ridiculous prices and behaved well in public. Outside Kabul and maybe Kandahar, the locals were as conservative then as they are now, if not more so. That was my impression. A group of Peace Corps kids I ran into as they were leaving said it was really primitive back in the hills. From what I read now, including Stewart's book, it seems as if not much has changed, except the hippies with hash pipes running around in sandals and beads have been replaced by guys with guns wearing sunglasses and boots. Apparently they are not as well tolerated. ;}