Originally Posted by
Southerner
Cookerhiker's suggestion of 43 to Punchbowl is a good one.
Another option you might consider is getting dropped off at the Belfast Trail, hiking past Devil's Marbleyard, connecting with the AT 2.8 miles south of Matts Creek Shelter, then taking the AT north to the US 56 crossing (Tye River). That would be 52.2 miles on the AT and about 3.2 miles on the Belfast Trail. Highlights would include Devil's Marbleyard, James River & the Foot Bridge, Fuller Rocks / Rocky Rows, Bluff Mountain, Brown Mountain Creek, Cold Mountain, Tar Jacket Ridge, Spy Rock, (Crabtree Falls off-trail), and the Priest. As far as trail towns, you could hitch into Glasgow or Big Island at US 501 (not much in either place, unfortunately), hitch into Buena Vista at US 60 (good town, but a long hitch at 9 miles), and walk into Montebello at the Fish Hatchery Road just before Spy Rock. I haven't been, but I've heard the Dutch Haus in Montebello is a very nice hostel, which might add to the replicated hiker experience. The only major drawback to the section for relative newbies is the rather hard climb from Brown Mountain Creek across US 60 and to the top of Bald Knob, which, insult to injury, isn't even bald (though Cold Mountain to its north is bald).
Oh, and the info. above about Shenandoah Nat'l Park not allowing dispersed camping is incorrect, just in case that weighs on your consideration. I think the poster was getting it confused with Great Smoky Mountains Nat'l Park. Shenandoah has a set of rules to follow about distances from trails, roads, water, etc., but does allow dispersed camping without having to max out shelters. In fact, they have signs up at some of the huts (shelters) saying that huts can only be used by people out for three or more nights.