Here's a fellow who getting ready to hike the Pacific Coast Trail (2,560 miles). I've always had an urge to do something like this, maybe start off smaller and do the Long Trail in Vermont, or longer sections of the Appalachian Trail. My nephew Jake and I hiked a little bit of the Long Trail a few years ago. It was fun but mega-buggy. Over the years I must have hiked a dozen sections of the Appalachian, but nothing over sixteen miles at a shot (it's 2,160 miles). There's a newer trail in New Hampshire, the COHOS Trail we haven't tried yet. Another killer trail is the Continental Divide Trail from Mexico to Canada (3,100 miles). Mom has a friend who's worked on sections of it in Wyoming. Just from what I know of the Wyoming portion it is quite varied and spectacular.