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Cross Country Expedition

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A friend and I will be doing a 6 week cross country expedition in a few months. For a two week period plan to go from Kentucky to Maine. Neither of us have ever been to the north eastern states. Preferred route through WV and Pennsylvania, staying clear of the big cities (or any population as far as that goes). We would like to do this on as much back country trails as possible. I'm from So Cal and my friend is from Canada so no heavy duty rock crawling. We want to limit breakdowns, but would still like trails with some challenges. The goal is to hit through trails rather than loops so we can gain about 150 miles to 200 miles per day. Looking for people with knowledge of part or all of these areas who can provide some guidance on planning our travels.