Virginia recommendations

Wild ponies are there. Great views. What's not to like? May be somewhat out of your way. N of Damascus, AT runs through it as well as other trails. Easy to do a loop hike there.

I have not done St. Mary's but I hear its good, and I believe you can do a loop there. Grayson Highlands is a bit of a drive but its amazing. The AT and the Crest Trail make a loop through some of the most scenic country up there. I'd guess the loop is about 13 miles if you start from Grayson Highlands Stat Park. If you start from Elk Garden you can do a "Lolipop" loop thats more like 18-20 miles but it includes even more amazing scenery. Get the Trails Illustrated map of the area. Its a good guide to the trails and it identifies the springs where you can get water. I suggest an over nighter and a camp along the ridge somewhere in one of the meadows.

Here are some pictures of a fall hike. It will be greener when you go.

Lots of great options. You can't go wrong with Grayson Highlands/Mt. Rogers area.

Saint Mary's Wilderness is beautiful and quite popular. There really aren't views there but great waterfall and stream valleys, plus some interesting vegetation and old ruins of mines.

For more options in the general vicinity of St. Mary's, check out Shenanodoah National Park's southern district for some great hikes in the Brown Mountain/Rockytop/Big Run area. Or head to the Blue Ridge Parkway area for a great backpack of Three Ridges (~15 miles).

Helpful links:

http://www.hikingupward.com
http://www.midatlantichikes.com

Thanks for the suggestions so far. I've never been anywhere north of South Carolina as far as Eastern US goes. I'll definitely take a look at these places.