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It'd be easier if you had included a scale in your map. Depending on what the distances are you might be able to walk and sleep at a different location each day.
https://www.google.com/maps/place/Rosman,+NC,+USA/@35.111419,-82.9341445,13.15z/data=!4m5!3m4!1s0x8859a8d2b8ac0163:0xc0f480356f0102b8!8m2!3d35.143721!4d-82.8212432 shows relatively small distances ...
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