I think you should look at some more options based on what you want from this change of pace you're considering.

The truth is, you most certainly will end up where there is no legal place to camp or even rent a room, and yes, people will mess with you when you camp on private land and they will call the law on you. That doesn't necessarily mean you'll be arrested or charged with a crime, but that potential is raised in those situations.

It's worth considering some of the advantages of a long distance trail hike like you'd have on the Appalachian Trail. You'll have places to camp out legally, places to restock supplies, and amazing scenery most all of the way. Crazy as it is, most of the long backpacking trails are not crowded, and you can always get off and walk to the nearest town to get a burger or slice of pizza, and even a night in a room with a shower and a bed.

It's a long hike to do the AT in one shot without running into some cold weather. I don't know much about any of those trails but I'm pretty sure that if you took your time and just meandered along it you could spend all Spring, Summer, and Autumn hiking it and not finish it.

Between the AT and the Pacific Crest Trail, which is also a very long hike, there are many other really great trails that run through some really cool areas and in all of them you'll find something different and challenging and you can test your endurance as much as you want on any of them.

Along any of the backpacking trails you're on you're sure to meet some great people who share your interest in getting out and away from the grind and you won't find yourself in a place where you're legally out of bounds.

If you're new to backpacking you'll have a lot easier time gaining the experience and honing the skills you need to be comfortable because you'll have better and more options as to when and where you'll set up camp for the night, and your route will be mostly within areas where those options are least limited.

And, if you complete any of the longer trails like the AT or PCT, you'll be a member of a very exclusive club. If you really want to go big you can hike the Triple Crown of Trails. Do that and you're among the backpacking elites wink

The main thing I'll ask you to consider is that you can chose to walk and camp in some incredibly beautiful areas on trails that are created just for that purpose. If you haven't done much of that, I'd offer it's a better place to start.

At the very least, I suggest you get all your gear together and start off with some short trips to get to know your gear, and then a couple longer trips, a week or two if you can, to get to know yourself once you've been out there more than a night or two, and then start making your plans for a long distance hike.
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